Plicamycin - Moligand™, ≥95% , CAS No.18378-89-7

CAS: 18378-89-7 Cat. No.: P113149 Molecular Weight: 1085.15 Beilstein Registry Number: 5236667 EC Number: 634-048-4

GRADE & PURITY Moligand™, ≥95%

Synonyms

Mithramycin A | Aurlelic acid | DB06810 | PA-144 | MITHRAMYCINA | MITHRAMYCIN | BDBM50547623 | Plicamycin [USAN:USP:INN:BAN] | PLICAMYCIN [USAN] | D00468 | Antibiotic LA 7017 | Mithramycinum | Mitramycine | plicamycin | Aureolic acid | CCRIS 5629 | NJWSNN

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Mithramycin A is an antibiotic DNA/RNA polymerase and DNA binding transcriptional inhibitor observed to facilitate TNF-α and Fas-ligand induced apoptosis. As a DNA binding transcriptional inhibitor, mithramycin A binds to GC rich sequences located in the minor groove of DNA and is noted to be reversible and Mg2+ dependent. Additionally reported to a block transcriptional activation of the SV40 promoter via competitive binding against Sp1 transcription factor to GC rich areas in the early promoter. Mithramycin A is noted to supress TNF-α induced expression of fractalkine (CX3CL1) mRNA in a dose-dependent manner and to act as an effective differentiation agent of HL60 promyelocytic leukemia cells
A polymerase inhibitor that binds to GC rich sequences located in the minor groove of DNA;DNA binding fluorescent dye. Until 2000 it was used to reduce high levels of plasma calcium; Used as an antineoplastic agent

Specifications

Synonyms

Mithramycin A | Aurlelic acid | DB06810 | PA-144 | MITHRAMYCINA | MITHRAMYCIN | BDBM50547623 | Plicamycin [USAN:USP:INN:BAN] | PLICAMYCIN [USAN] | D00468 | Antibiotic LA 7017 | Mithramycinum | Mitramycine | plicamycin | Aureolic acid | CCRIS 5629 | NJWSNN

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

Anticancer antibiotic. Inhibits transcription and protein synthesis. Binds to DNA in native chromatin. Substrate of Pgp in MDR phenotypes.DNA and RNA polymerase inhibitor, DNA binding transcriptional inhibitor (Sp1 and Sp3). Shows antineoplastic activity.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

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.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 504757537
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757537
• Canonical Smiles: CC1C(C(CC(O1)OC2CC(OC(C2O)C)OC3=CC4=CC5=C(C(=O)C(C(C5)C(C(=O)C(C(C)O)O)OC)OC6CC(C(C(O6)C)O)OC7CC(C(C(O7)C)O)OC8CC(C(C(O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O
• IUPAC Name: (2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one
• InChIKey: CFCUWKMKBJTWLW-BKHRDMLASA-N
• INCHI: 1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27+,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43-,44-,45+,49+,50+,51-,52+/m1/s1
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2C[C@@H](O[C@@H]([C@H]2O)C)OC3=CC4=CC5=C(C(=O)[C@H]([C@@H](C5)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)O)O[C@H]7C[C@H]([C@H]([C@H](O7)C)O)O[C@H]8C[C@]([C@@H]([C@H](O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O
• WGK Germany: 3
• RTECS: PZ2800000
• UN Number: 2811
• Molecular Weight: 1085.15
• Beilstein: 5236667
• Reaxy-Rn: 24710368
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24710368&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Not available
• Direct Parent: Oligosaccharides
• Alternative Parents: Anthracenes Naphthols and derivatives O-glycosyl compounds Tetralins Aryl alkyl ketones 1-hydroxy-4-unsubstituted benzenoids Oxanes Beta-hydroxy ketones Acyloins Vinylogous acids Alpha-hydroxy ketones Tertiary alcohols Secondary alcohols Oxacyclic compounds Acetals Dialkyl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Oligosaccharide - Anthracene - Glycosyl compound - 1-naphthol - O-glycosyl compound - Tetralin - Aryl ketone - Aryl alkyl ketone - 1-hydroxy-4-unsubstituted benzenoid - Benzenoid - Oxane - Acyloin - Beta-hydroxy ketone - Vinylogous acid - Tertiary alcohol - Alpha-hydroxy ketone - Secondary alcohol - Ketone - Organoheterocyclic compound - Oxacycle - Acetal - Ether - Dialkyl ether - Hydrocarbon derivative - Carbonyl group - Alcohol - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
• External Descriptors: anthracycline antibiotic - carbohydrate-containing antibiotic - aureolic acid

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

Associated Targets(Human)

A673 (619 Activities)

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DU-145 (51482 Activities)

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PANC-1 (6144 Activities)

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PC-3 (62116 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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Prostatic carcinoma cell (85 Activities)

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LNCaP (8286 Activities)

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HeLa (62764 Activities)

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DMS-114 (15429 Activities)

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U-118-MG (352 Activities)

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ES8 (149 Activities)

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ES7 (149 Activities)

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EWSR1 Tbio Friend leukemia integration 1 transcription factor (Proto-oncogene Fli-1)/RNA-binding protein EWS (19 Activities)

Discover Target: EWSR1

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TC-32 (111 Activities)

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VCaP (1078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in phosphate buffered saline (1 mg/ml), ethanol, ethyl acetate, lower alcohols, and acetone. Insoluble in water.
• Sensitivity: light sensitive & Moisture sensitive
• Melt Point(°C): 170-175°C
• Molecular Weight: 1085.100 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 24
• Rotatable Bond Count: 15
• Exact Mass: 1084.47 Da
• Monoisotopic Mass: 1084.47 Da
• Topological Polar Surface Area: 358.000 Ų
• Heavy Atom Count: 76
• Formal Charge: 0
• Complexity: 1940.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 25
• 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

References

1. Danfeng Wang, Min Liu, Yushu Wu, Tianxin Weng, Lu Wang, Yongfang Zhang, Yanna Zhao, Jun Han.  (2022)  Idarubicin/mithramycin-acridine orange combination drugs co-loaded by DNA nanostructures: Different effects of intercalation and groove binding on drug release and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2022.118947]

2. Danfeng Wang, Min Liu, Yushu Wu, Yanna Zhao, Qingpeng Wang, Tianxin Weng, Lu Wang, He Liu, Yongfang Ren, Jun Han.  (2021)  Self-assembled DNA nanotrains for targeted delivery of mithramycin dimers coordinated by different metal ions: Effect of binding affinity on drug loading, release and cytotoxicity.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2021.116722]