Adriamycin - Moligand™, ≥97% , Inhibitor of DNA topoisomerase II alpha, CAS No.23214-92-8, Inhibitor of DNA topoisomerase II alpha

CAS: 23214-92-8 Cat. No.: A183027 Fórmula: C₂₇H₂₉NO₁₁ Peso molecular: 543.5 Número EC: 245-495-6 PubChem CID: 31703

CALIDAD & PUREZA Moligand™, ≥97%

Synonyms

Adriablastin|hydroxydaunomycin|Hydroxyldaunorubicin|Doxorubicine|Doxorubicina [INN-Spanish]|DOXORUBICIN (MART.)|Doxorubicinum [INN-Latin]|14-Hydroxydaunomycin|Doxil|ADM|Hydroxyl Daunorubicin|Doxorubicine (INN-French)|(1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-(3-amino-2,3,6-tridesoxy-alpha-L-lyxo-hexopyranosid)|(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione|VALRUBICIN IMPURITY, DOXORUBICIN [USP IMPURITY]|doxorrubicina|Doxorubicin-P4/D10 conjugate|DOXORUBICIN [VANDF]|Hydroxydaunorubicin|(1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside|VALRUBICIN IMPURITY, DOXORUBICIN (USP IMPURITY)|Doxorubicin (USAN/INN)|Doxorubicin-hLL1|(8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione|Adriamycin|ADR|ThermoDox|(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside|Conjugate of doxorubicin with humanized monoclonal antibody LL1 against CD74|(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione|Adriamycin semiquinone|doxorubicin|(8S-cis)-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione|Caelyx (liposomal doxorubicin)|1,2,3,4,6,11-Hexahydro-4beta,5,12-trihydroxy-4-(hydroxyacetyl)-10-methoxy-6,11-dioxonaphthacen-1beta-yl-3-amino-2,3,6-trideoxy-alpha-L-lyxohexopyranoside|Doxorubicina (INN-Spanish)|5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-|DOXORUBICIN [MI]|Doxorubicina|(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside|DOXORUBICIN [INN]|DOXORUBICIN [WHO-DD]|Doxorubicine [INN-French]|Epirubicin hydrochloride impurity, doxorubicin-|DM2|(8S,10S)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione|Conjugate of doxorubicin with monoclonal antibody P4/D10 against GP120|DOXORUBICIN [HSDB]|DOXORUBICIN [USAN]|DOXORUBICIN [MART.]|Doxorubicin [USAN:INN:BAN]|(8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE|(8S-cis)-10-|5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-|Doxorubicin-P4/D10|Doxorubicinum|FI 106|5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-|14-Hydroxydaunorubicine|Doxorubicin-hLL1 conjugate|Valrubicin impurity, doxorubicin|Adriblastina (TN)|GR-319

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

Adriamycin is a Topoisomerase II catalytic inhibitor, also is a broad spectrum antibiotic used in the treatment of cancers.

Especificaciones

Sinónimos

Adriablastin | hydroxydaunomycin | Hydroxyldaunorubicin | Doxorubicine | Doxorubicina [INN-Spanish] | DOXORUBICIN (MART.) | Doxorubicinum [INN-Latin] | 14-Hydroxydaunomycin | Doxil | ADM | Hydroxyl Daunorubicin | Doxorubicine (INN-French) | (1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-( Show more

Especificaciones y pureza

Moligand™, ≥97%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

Inhibitor of DNA topoisomerase II alpha

Pureza

≥97%

Nombres e identificadores

Sonrisas canónicas

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O

IUPAC Name

(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

InChIKey

AOJJSUZBOXZQNB-TZSSRYMLSA-N

INCHI

1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1

Isómeros SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O

PubChem CID

31703

Peso molecular

543.5

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Anthracyclines

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Anthracyclines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracyclines
• Alternative Parents: Tetracenequinones Aminoglycosides Anthraquinones Hexoses O-glycosyl compounds Tetralins Anisoles Aryl ketones Alkyl aryl ethers Oxanes Tertiary alcohols Vinylogous acids Alpha-hydroxy ketones Secondary alcohols 1,2-aminoalcohols Oxacyclic compounds Acetals Polyols Organopnictogen compounds Organic oxides Primary alcohols Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthracycline - Anthracyclinone-skeleton - Aminoglycoside core - Tetracenequinone - 9,10-anthraquinone - 1,4-anthraquinone - Anthracene - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Tetralin - Aryl ketone - Anisole - Amino saccharide - Alkyl aryl ether - Benzenoid - Oxane - Monosaccharide - Vinylogous acid - Tertiary alcohol - Alpha-hydroxy ketone - Secondary alcohol - 1,2-aminoalcohol - Ketone - Acetal - Organoheterocyclic compound - Polyol - Ether - Oxacycle - Alcohol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Amine - Primary amine - Primary alcohol - Primary aliphatic amine - Organonitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
• External Descriptors: Anthracyclinones

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

TOP2B Tclin DNA topoisomerase 2-beta (1 Activities)

Discover Target: TOP2B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TOP2A Tclin DNA topoisomerase 2-alpha (6 Activities)

Discover Target: TOP2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)

Discover Target: PDE5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DHFR Tclin Dihydrofolate reductase (3072 Activities)

Discover Target: DHFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

F2 Tclin Thrombin (11687 Activities)

Discover Target: F2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HMGCR Tclin HMG-CoA reductase (2475 Activities)

Discover Target: HMGCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

INSR Tclin Insulin receptor (5558 Activities)

Discover Target: INSR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PRSS1 Tclin Trypsin I (2306 Activities)

Discover Target: PRSS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

Discover Target: ADRB2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

Discover Target: CHRM2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

Discover Target: ADRB1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

Discover Target: ADRA2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP1 Tclin DNA topoisomerase I (7553 Activities)

Discover Target: TOP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

Discover Target: TOP2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACE Tclin Angiotensin-converting enzyme (1423 Activities)

Discover Target: ACE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

Discover Target: DRD2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

Discover Target: GABRA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

Discover Target: CNR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

Discover Target: DRD4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

Discover Target: PTGS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH2 Tclin Histamine H2 receptor (5428 Activities)

Discover Target: HRH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)

Discover Target: ADRA1D

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

Discover Target: MAOB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR1B Tclin Serotonin 1b (5-HT1b) receptor (2801 Activities)

Discover Target: HTR1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

Discover Target: HTR2C

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

Discover Target: AVPR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

Discover Target: ADORA1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

Discover Target: AGTR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CALCR Tclin Calcitonin receptor (2215 Activities)

Discover Target: CALCR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A4 Tclin Serotonin transporter (12625 Activities)

Discover Target: SLC6A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

Discover Target: PTGS2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HRH1 Tclin Histamine H1 receptor (7573 Activities)

Discover Target: HRH1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)

Discover Target: ADRA1B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRM1 Tclin Mu opioid receptor (19785 Activities)

Discover Target: OPRM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

Discover Target: AVPR1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

OPRD1 Tclin Delta opioid receptor (15096 Activities)

Discover Target: OPRD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Agtr2 Angiotensin II type 2 (AT-2) receptor (803 Activities)

Discover Target: Agtr2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mc4r Melanocortin receptor 4 (1205 Activities)

Discover Target: Mc4r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ltc4s Leukotriene C4 synthase (1 Activities)

Discover Target: Ltc4s

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Sigmar1 Sigma opioid receptor (160 Activities)

Discover Target: Sigmar1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Npy1r Neuropeptide Y receptor type 1 (8 Activities)

Discover Target: Npy1r

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

polA Taq polymerase 1 (482 Activities)

Discover Target: polA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cckar Cholecystokinin A receptor (90 Activities)

Discover Target: Cckar

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PIK3CA PI3-kinase p110-alpha subunit (51 Activities)

Discover Target: PIK3CA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Pde4d Phosphodiesterase 4D (4 Activities)

Discover Target: Pde4d

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cpt1a Carnitine palmitoyltransferase 1A (532 Activities)

Discover Target: Cpt1a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcc1 Multidrug resistance-associated protein 1 (42 Activities)

Discover Target: Abcc1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb1b P-glycoprotein 1 (174 Activities)

Discover Target: Abcb1b

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nos2 Nitric oxide synthase, inducible (3573 Activities)

Discover Target: Nos2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp2 Matrix metalloproteinase-2 (12 Activities)

Discover Target: Mmp2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mmp9 Matrix metalloproteinase 9 (38 Activities)

Discover Target: Mmp9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

Discover Target: pol

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Abcb1a P-glycoprotein 3 (492 Activities)

Discover Target: Abcb1a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Top2 DNA topoisomerase II (15 Activities)

Discover Target: Top2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HD1 Histone deacetylase (38 Activities)

Discover Target: HD1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cacna1g Voltage-gated T-type calcium channel alpha-1G subunit (1 Activities)

Discover Target: Cacna1g

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trichophyton benhamiae (1686 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Artemia salina (1320 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Agrobacterium tumefaciens (620 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Salmonella typhimurium (15756 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus epidermidis (22802 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Streptococcus pyogenes (16140 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mycobacterium tuberculosis (203094 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Saccharomyces cerevisiae (19171 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus cereus (7522 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: ≥27.2 mg/mL in DMSO; insoluble in EtOH; ≥24.8 mg/mL in H2O with ultrasonic
• Sensibilidad: light & heat sensitive
• Peso molecular: 543.500 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 543.174 Da
• Monoisotopic Mass: 543.174 Da
• Topological Polar Surface Area: 206.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 977.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

• Item-specific tested applications and conditions: Not specified for this item; refer to CoA/Spec Sheet.

• General research practices (literature/examples; not validated for this specific item)

  • Stock preparation: Dissolve in anhydrous DMSO to 10–20 mM; vortex and sonicate briefly if needed. Filter through 0.22 µm PTFE if particulate remains.
  • Fluorescence readout: For solution studies, excite at ~480–500 nm and collect emission 560–600 nm. Use matched blanks to correct for buffer/cosolvent background.
  • Nucleic acid binding assays: Titrate ligand into buffered DNA solution (e.g., 10 mM phosphate, 100 mM NaCl, pH 7.0) and monitor spectral shifts or fluorescence quenching/enhancement.
  • Conjugation (C-13 hydrazone): Mix Adriamycin with hydrazide linker in 50 mM acetate buffer, pH 5.5, 10% DMSO; incubate at RT 4–16 h; purify by RP-HPLC.

Always validate and optimize conditions for your system and consult institutional SOPs. These examples are informational and not product-specific recommendations.

Biological Roles

• Literature/general background (no clinical claims)

  • Origin: An anthracycline natural product derivative historically associated with Streptomyces peucetius. Functions as a polycyclic quinone glycoside with DNA intercalating ability in research contexts.
  • Molecular interactions: Intercalates between nucleic acid base pairs and is known to stabilize DNA-topoisomerase II cleavage complexes in mechanistic studies (literature). The quinone/hydroquinone system participates in redox cycling under certain conditions.
  • Cellular effects (research context): Modulates nucleic acid topology and replication-associated processes in a wide range of cell models, frequently used as a benchmark cytotoxic compound for assay development and pathway interrogation (literature).
  • Spectroscopic utility: Intrinsic fluorescence supports live-cell imaging method development and uptake/efflux studies in model systems, enabling transporter and permeability research without external dyes (literature).

• Biochemical parameters (literature)

  • Binding: Affinity to DNA varies with sequence and ionic strength; GC-rich regions often show stronger intercalation signals.
  • pH dependence: Protonation state (amine pKa ~8.2–8.6) influences membrane interaction and nucleic acid binding.

• Notes

  • All uses are for laboratory research only. Actual behavior depends on cell type, buffer composition, exposure time, and illumination; validate in each system.

Buffer Applications

Adriamycin is not a conventional buffering agent. However, buffer choice strongly impacts its solubility, stability, and reactivity in research workflows.

• Practical buffer guidance (literature/general)

  • Stock preparation: Dissolve in DMSO to 10–20 mM (typical in literature), then dilute into buffer. Alternatively, dissolve the protonated form (e.g., hydrochloride) directly in aqueous buffer at pH 5.5–7.4.
  • Working pH: Slightly acidic to neutral buffers (acetate pH 5.0–6.0; phosphate pH 6.5–7.4) balance solubility and stability. Avoid strong base (≥pH 9) which accelerates degradation.
  • Light and oxygen: Use amber tubes and minimize headspace for longer incubations; add antioxidant only if compatible with the assay, as redox-active additives can alter outcomes.
  • Ionic strength: Moderate ionic strength (e.g., PBS) supports reproducible binding assays with nucleic acids and proteins; adjust salt to tune intercalation or binding phenomena.

• Example buffer choices (general)

  • 50–100 mM sodium phosphate, pH 7.0–7.4 (spectroscopy, binding assays).
  • 50 mM sodium acetate, pH 5.5–6.0 (hydrazone/oxime ligations at the C-13 carbonyl).

• Not a buffering component: Do not use Adriamycin to establish pH; select appropriate buffering agents and verify pH after adding organic cosolvents.

Green Alternatives

Because Adriamycin is an active research ligand rather than a process solvent or bulk reagent, “green replacement” discussions focus on handling media and auxiliary reagents rather than substituting the active itself.

• Greener handling choices (general/literature)

  • Prefer aqueous buffers at controlled pH (5.5–7.4) over chlorinated or high-VOC solvents when feasible.
  • Use DMSO as the primary organic cosolvent; it offers high solvating power and favorable EHS profile versus DMF or NMP in many settings.
  • Minimize solvent volumes through concentrated stock solutions and microplate-based assays to reduce waste.

• Comparison of common media (general)

  • Aqueous buffer (acetate, phosphate): Low environmental impact; supports stability at moderate pH; may require cosolvent for high concentrations.
  • DMSO: High solubilizing power; low volatility; readily compatible with downstream aqueous dilution; consider proper waste management.
  • Alcohol/water mixes: Can be used but may compromise stability and introduce volatility; less preferred than DMSO for concentrated stocks.

• Operational green tips

  • Protect from light to minimize degradation and waste.
  • Adopt closed-well, small-volume assays and validated deactivation/cleanup protocols to reduce exposure and disposal burden.

Pharmaceutical Uses

No therapeutic claims are made. The following pertains to research and development contexts only.

• Formulation and delivery research (literature/general)

  • Model cytotoxic payload: Frequently used in preclinical studies to evaluate delivery platforms (e.g., liposomes, polymeric micelles, nanoparticles) and to benchmark release kinetics, permeability, and stability.
  • Conjugation studies: Serves as a payload in antibody–drug conjugate (ADC) method development via C-13 hydrazone linkers or amide linkages through the daunosamine amine.
  • Excipient interactions: Binding to serum proteins and components of lipid systems is often characterized to understand distribution behavior in model systems.

• Pharmacopeial/compendial status

  • Any monograph or compendial status is not specified for this item; refer to CoA/Spec Sheet.

• Manufacturing notes (research only)

  • Light- and pH-sensitive; formulation screening typically explores pH 5–7 buffers, chelators to limit metal-catalyzed degradation, and lyophilization for stability in development settings (literature).
  • Analytical controls: Stability-indicating HPLC/UPLC with fluorescence or UV detection near 480–500 nm is commonly employed (literature).

Physical Properties

• Item-specific specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed values (for reference; not item specifications)

  • Physical state: Solid (anthracycline aglycone glycoside); tends to be red to orange crystalline powder (literature).
  • Melting behavior: Decomposes on heating; distinct melting point not typically reported (literature).
  • Solubility: Free base is sparingly soluble in water; highly soluble in polar organics (e.g., DMSO, DMF). Hydrochloride salt is water-soluble (literature).
  • pKa: Primary amine on daunosamine pKa ~8.2–8.6; phenolic pKa values higher and less relevant under neutral conditions (literature).
  • LogP/logD: logP (neutral) ~1.3–1.4; logD7.4 reduced due to protonation of amine (literature).
  • UV-Vis: Strong absorption bands near ~233, 254, 480–500 nm depending on solvent and pH (literature).
  • Fluorescence: Excitation ~470–500 nm; emission ~560–600 nm with environment dependence (literature).
  • Stability considerations: Anthracycline quinone/hydroquinone chromophore is sensitive to prolonged light exposure and oxidative/reductive conditions; aqueous solutions may slowly degrade, especially at alkaline pH (literature).

• Density, refractive index, vapor pressure: Not typically applicable/reported for this polyfunctional solid (literature).

Quality and Grades

• Item-specific

  • Grade/Purity: Moligand™ (as provided).

• Interpretation and implications (general)

  • Moligand™ designation indicates suitability as a research-grade molecular ligand for biochemical, chemoproteomic, binding, or conjugation studies. While not a clinical grade, such materials are typically prepared to support reliable in vitro/in vivo exploratory research where defined identity and performance are critical.
  • Identity: For small-molecule ligands like Adriamycin, identity is commonly supported by orthogonal methods (e.g., HPLC/UPLC purity profile, MS, and 1H/13C NMR). Specific item certificates provide the definitive acceptance criteria.
  • Purity: Exact assay, impurity thresholds (e.g., related anthracyclines), residual solvents, water content, metals, and UV cutoffs are batch-dependent. Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers: None specified for this item; refer to CoA/Spec Sheet. Anthracyclines are sometimes provided without stabilizers; if present, stabilizers can influence spectral baselines and bioconjugation chemistry.

• Fit-for-purpose selection

  • Choose Moligand™ grade when the objective is mechanistic biochemistry, target engagement assays, fluorescence tracking, or conjugation method development, as opposed to analytical reference standard or GMP needs.
  • For LC-based quantitation or impurity profiling, consider also obtaining a reference standard grade where available.

Reaction and Applications

This compound is primarily a bioactive research ligand rather than a commodity reagent; however, its chemistry and photophysics enable several laboratory applications.

• Biochemical applications (literature/general)

  • DNA/RNA interaction studies: Acts as a classic intercalator; used to study nucleic acid binding thermodynamics and topology (e.g., topoisomerase II–related assays) in research contexts.
  • Fluorescent tracer: Intrinsic fluorescence (Ex ~480–500 nm/Em ~560–600 nm, solvent-dependent) allows label-free visualization in model systems.

• Chemical/derivatization applications (literature)

  • C-13 carbonyl is amenable to hydrazone/oxime formation with hydrazide/alkoxyamine partners (common in prodrug and conjugation method development).
  • Daunosamine primary amine can be acylated or coupled to activated esters (e.g., NHS esters) to form amide-linked conjugates. Protecting-group strategies may be required to control site-selectivity.
  • Quinone/hydroquinone redox couple participates in electron-transfer studies; reduction can transiently alter spectral properties.

• Practical tips

  • Work under subdued light; store working solutions on ice when feasible. Use freshly prepared buffers at slightly acidic to neutral pH (ca. 5.5–7.4) to balance stability and solubility.
  • For bioconjugation at the C-13 ketone, mildly acidic acetate buffers (pH 5–6) often improve hydrazone formation; aniline catalysts can accelerate oxime ligations (literature).
  • For amide couplings on the sugar, avoid over-acylation/hydrolysis by using stoichiometric control and monitoring by LC-MS.

Reaction Conditions

The following are general literature conditions for derivatization and conjugation; they are not specifications for this item.

• Hydrazone formation at C-13 ketone (literature example)

  • Reagents: Hydrazide-bearing linker (1.2–3.0 eq).
  • Solvent/buffer: 50 mM sodium acetate, pH 5.0–5.5, with 5–20% DMSO to aid solubility.
  • Temperature/time: RT to 37°C, 2–16 h.
  • Notes: Remove dissolved oxygen/light exposure where possible; aniline (10–100 mM) can catalyze oxime formation with alkoxyamines.

• Amide coupling on daunosamine amine (literature example)

  • Reagents: NHS-activated esters or EDC/NHS with carboxylate partners.
  • Solvent: Aqueous buffer (pH 7–8) with DMSO or DMF cosolvent; or anhydrous DMF for preactivation.
  • Temperature/time: 0–25°C, 1–6 h; monitor by LC-MS.
  • Notes: Competing phenolic acylation can occur; transient protection or micellar media can improve selectivity.

• Reductive modifications (literature)

  • Quinone reduction: Sodium dithionite or electrochemical methods under controlled conditions; monitor to avoid over-reduction of sensitive centers.

• Spectroscopy/assay conditions (general)

  • UV-Vis/fluorescence: Measure in phosphate buffer (pH 7.0) or DMSO; Exc ~480–500 nm, Em ~560–600 nm. Use low micromolar concentrations to avoid inner-filter effects.

Safety and Handling

• Item-specific hazard data

  • GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.

• General laboratory precautions (professional guidance; defer to SDS as authoritative)

  • Handle in a chemical fume hood to minimize inhalation and exposure; avoid aerosol generation.
  • Wear appropriate PPE: lab coat, nitrile gloves (double-gloving recommended for cytotoxic research chemicals), and safety glasses/face shield.
  • Prevent skin/eye contact; avoid ingestion and inhalation. Use closed containers and secondary containment during transport in the lab.
  • Decontamination: Wipe work surfaces with suitable deactivating/oxidizing agents compatible with anthracyclines, followed by detergent and water (check institutional SOPs).
  • Waste: Collect contaminated disposables and solutions as hazardous chemical waste per institutional and regulatory requirements.

• Incompatibilities and special risks (literature/general)

  • Light- and pH-sensitive; avoid prolonged exposure to strong light, strong bases, and strong oxidizers/reductants that can degrade the quinone chromophore.
  • Do not autoclave solutions in closed vials; pressure buildup and degradation may occur.
  • Avoid contact with reactive carbonyl- or amine-modifying reagents unless derivatization is intended (compound bears both amine and ketone functionalities).

• First-aid overview (general)

  • Skin/eye contact: Immediately flush with water for ≥15 minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention.
  • Ingestion/needlestick: Seek immediate medical attention per institutional exposure protocols.
  • Always consult the product SDS for definitive, item-specific safety guidance.

Solvent Selection

• Polarity and ionization (literature/general)

  • Adriamycin contains a protonatable primary amine (daunosamine) and multiple hydroxyls, plus a hydrophobic anthracycline core. As the free base it is amphipathic and moderately lipophilic; as its protonated form it is significantly more water-compatible.

• Practical solvent choices (research guidance)

  • Stock solutions: DMSO is widely used to prepare concentrated stocks (e.g., 10–20 mM, literature). Aqueous buffers (pH ~4.5–7) can dissolve the protonated form; the hydrochloride salt exhibits higher aqueous solubility.
  • Working solutions: Dilute DMSO stocks into buffered saline, PBS, or culture media substitutes while keeping final DMSO ≤0.1–1% depending on system tolerance (user SOP-dependent).
  • Avoid strong bases (≥pH 9) which can accelerate degradation of the anthracycline chromophore.

• Miscibility/compatibility (literature)

  • Highly soluble in DMSO and DMF; limited in pure alcohols and very limited in nonpolar solvents (hexanes, toluene). Cosolvent systems (water/alcohol) may be used if pH is controlled.

• Comparison notes (general)

  • Relative to highly hydrophobic dyes, Adriamycin’s protonatable amine eases aqueous handling. Compared with permanently charged fluorophores, its solubility is more pH-dependent; buffer control is therefore more critical.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage: Store at 2–8°C (as provided in Product Data). Protect from light.
  • Shipped in: Wet ice (as provided).

• Reconstitution (item-specific status)

  • No specific reconstitution solvent or concentration is specified for this item; refer to CoA/Spec Sheet.

• General guidance (literature/practice; not item specifications)

  • For immediate use, prepare concentrated stocks in anhydrous DMSO (e.g., 10–20 mM) or, if supplied as an acid salt, in water or buffer at pH 5.5–7.4. Filter-sterilize if required by the application.
  • Aliquot stocks to minimize freeze–thaw and light exposure. Store aliquots protected from light; frozen DMSO stocks at ≤−20°C are common practice in research labs, but confirm compatibility with your workflow.
  • Aqueous working solutions are best prepared fresh. Avoid prolonged storage at alkaline pH.

• Stability notes

  • Anthracycline chromophores are light- and pH-sensitive; use amber vials and minimize headspace.
  • Do not expose to strong oxidants or bases during storage.

• Research Use Note

  • For research use only (as provided). Not for human or veterinary use.

Structure and Identity

Brief: Adriamycin (commonly known as doxorubicin) is an anthracycline polycyclic quinone with an amino sugar (daunosamine) glycoside.

• Item-specific (from Product Data)

  • SKU: A183027
  • Product name: Adriamycin
  • CAS: 23214-92-8
  • PubChem CID: 31703
  • InChIKey: 10725 (as provided)
  • Grade/Purity: Moligand™

• Literature identity (for reference; not item specifications)

  • Synonyms (literature): doxorubicin, hydroxydaunorubicin
  • Molecular formula (literature): C27H29NO11
  • Molecular weight (literature): ~543.52 g/mol (free base)
  • SMILES (literature): C[C@H]1C(=O)C2=C(C(=O)c3c(O)ccc(O)c3C2=O)CC@@H[C@@H]1O[C@H]1CC@@HCC@HC@HO1
  • InChIKey (literature): AOJJSUZBOXZQNB-QLFBSQMISA-N

• Structural features (general/literature)

  • Core: Tetracyclic anthracyclinone (anthraquinone-like) aglycone bearing phenolic and quinone functions.
  • Sugar: L-daunosamine (3-amino-2,3,6-trideoxy-L-fucose) at C-7 via O-glycosidic linkage.
  • Functional groups: Hydroquinone/quinone system, phenols, tertiary alcohol, ketone at C-13, primary amine on sugar, multiple secondary alcohols and an acetal.
  • Stereochemistry: Multiple defined stereocenters on the glycoside and side chain (literature absolute configuration as shown in SMILES above).
  • 2D description: A fused, planar aromatic system (three rings with quinone/phenolic substitution) attached via an oxygen bridge to a substituted cyclohexenone bearing a side-chain ketol; the amino-deoxysugar is linked through a glycosidic bond, projecting out of plane.

Synthetic Utility

Although primarily a bioactive ligand, Adriamycin’s densely functionalized scaffold provides versatile handles for derivatization in chemical biology and method development.

• Functional group leverage (literature/general)

  • C-13 ketone: Forms hydrazones/oximes (payload release linkers, reversible conjugation). Can be reduced to alcohol under controlled conditions.
  • Primary amine (daunosamine): Amenable to acylation, urea/thiourea formation, and coupling to NHS esters or isocyanates. Careful chemoselectivity required to avoid modifications at phenolic OH groups.
  • Phenolic hydroxyls: Undergo etherification/esterification; protection strategies (e.g., silyl, benzyl) often used in multistep syntheses.
  • Quinone: Participates in Michael-type additions and redox chemistry; reduction modulates reactivity and spectral properties.

• Retrosynthetic/value (literature)

  • Serves as a reference scaffold for SAR studies on anthracyclines, enabling exploration of sugar modifications, C-13 side chain tuning, and ring-substitution patterns.

• Practical considerations

  • Protect from light and control pH during transformations to limit side reactions (e.g., quinone degradation).
  • Use mild, selective coupling conditions (e.g., HATU/EDC on protected analogs; aniline-catalyzed oxime ligations at pH 4.5–6.0) and monitor by LC-MS due to complex impurity profiles.
  • Purification commonly via preparative RP-HPLC; strong chromophore facilitates UV-guided fractionation.

Target Specificity

This product is a small-molecule ligand and not an antibody or affinity reagent with defined antigen specificity.

• Item-specific tested target specificity: Not applicable/not specified for this item; refer to CoA/Spec Sheet.

• Literature context (general)

  • Interacts with nucleic acids via intercalation and influences topoisomerase II–mediated processes in mechanistic assays. These are broad biochemical interactions rather than selective binding to a single protein epitope.