Rubitecan - ≥98%(HPLC) , DNA topoisomerase I inhibitor, CAS No.91421-42-0, DNA topoisomerase I inhibitor

CAS: 91421-42-0 Cat. No.: R139432 Peso molecular: 393.35 Número EC: 995-853-7 PubChem CID: 472335

GRADE & PURITY ≥98%(HPLC)

Synonyms

9-nitro-20-(S)-camptothecin | 9-nitro-20(S)-camptothecin | H19C446XXB | (4s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione | NaOCH3 | BCP06207 | Camptogen | BDBM50248354 | CAS-91421-42-0 | CHEBI:90225 | EX-A4

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Rubitecan (RFS 2000), a Camptothecin derivative, is an orally active topoisomerase I inhibitor with broad antitumor activity, and induces protein-linked DNA single-strand breaks, thereby blocking DNA and RNA synthesis in dividing cells.

Specifications

Sinónimos

9-nitro-20-(S)-camptothecin | 9-nitro-20(S)-camptothecin | H19C446XXB | (4s)-4-ethyl-4-hydroxy-10-nitro-1h-pyrano[3', 4':6, 7]indolizino[1, 2-b]quinoline-3, 14(4h, 12h)-dione | NaOCH3 | BCP06207 | Camptogen | BDBM50248354 | CAS-91421-42-0 | CHEBI:90225 | EX-A4

Especificaciones y pureza

≥98%(HPLC)

Mecanismos bioquímicos y fisiológicos

Topoisomerase I inhibitor. Rubitecan induces protein- linked DNA single strand breaks, blocking DNA and RNA synthesis in dividing cells. This mode of action makes rubitecan a potential chemotherapeutic agent, and it has been used with some success against

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

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

Tipo de acción

INHIBITOR

Mecanismo de acción

DNA topoisomerase I inhibitor

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%(HPLC)

Nombres e identificadores

• Pubchem Sid: 504758930
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758930
• Sonrisas canónicas: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5[N+](=O)[O-])N=C4C3=C2)O
• IUPAC Name: (19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
• InChIKey: VHXNKPBCCMUMSW-FQEVSTJZSA-N
• INCHI: 1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
• Isómeros SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5[N+](=O)[O-])N=C4C3=C2)O
• PubChem CID: 472335
• Peso molecular: 393.35
• Reaxy-Rn: 5365063

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Clase Camptothecins

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Clase: Camptothecins
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Camptothecins
• Alternative Parents: Nitroquinolines and derivatives Pyranopyridines Nitroaromatic compounds Pyridinones Benzenoids Tertiary alcohols Heteroaromatic compounds Carboxylic acid esters Lactones Lactams Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Azacyclic compounds Organic oxoazanium compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Organic zwitterions Carbonyl compounds Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Camptothecin - Nitroquinoline - Pyranopyridine - Quinoline - Nitroaromatic compound - Pyridinone - Pyridine - Benzenoid - Heteroaromatic compound - Tertiary alcohol - Carboxylic acid ester - Lactam - Lactone - C-nitro compound - Organic nitro compound - Organoheterocyclic compound - Azacycle - Oxacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organic oxoazanium - Organic zwitterion - Organic oxygen compound - Carbonyl group - Organonitrogen compound - Organic nitrogen compound - Alcohol - Organooxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
• External Descriptors: Not available

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)

F2 Tclin Thrombin (11687 Activities)

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

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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

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

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

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

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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A-375 (9258 Activities)

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Caco-2 (12174 Activities)

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HEK293 (82097 Activities)

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Jurkat (10389 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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HTT Tchem Huntingtin (19182 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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Objetivos asociados (no humanos)

Hdac6 Histone deacetylase 6 (222 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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P338 (231 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Rotación específica [α]: 39° (C=0.4,CHCl3:MeOH=8:2)
• Punto de fusión (°C): 268°C(lit.)
• Peso molecular: 393.300 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 393.096 Da
• Monoisotopic Mass: 393.096 Da
• Topological Polar Surface Area: 126.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 861.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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