6377-18-0

Basic information

• Product Name: CHARTREUSIN
• Synonyms: LAMBDAMYCIN;CHARTREUSIN;antibioticx-465a;nsc5159;u-7257;chartreusin from streptomyces*chartreusis;10-[[6-Deoxy-2-O-(6-deoxy-3-O-methyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]oxy]-6-hydroxy-1-methylbenzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione;LaMbdaMycin, NSC 5159, 747, 1293, X465A, G 261A
• CAS NO: 6377-18-0
• Molecular Formula: C32H32O14
• Molecular Weight: 640.59
• Product Categories: Antibiotic
• Mol File: 6377-18-0.mol

Chemical Properties

• Melting Point: 185℃
• Boiling Point: 592.39°C (rough estimate)
• Flash Point: 307.8°C
• Appearance: /
• Density: 1.3027 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6130 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly), Pyridine (Slightly)
• Water Solubility: 15mg/L(25 oC)
• Stability: Hygroscopic
• CAS DataBase Reference: CHARTREUSIN(CAS DataBase Reference)
• NIST Chemistry Reference: CHARTREUSIN(6377-18-0)
• EPA Substance Registry System: CHARTREUSIN(6377-18-0)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36/37/39-45
• Hazardous Substances Data: 6377-18-0(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Chartreusin is utilized as an antitumor antibiotic in the field of oncology. It is effective in targeting and binding to GC-rich regions in DNA, which is a common feature in many cancer cells. By inhibiting RNA synthesis and causing DNA single-strand scission through the formation of free radicals, Chartreusin disrupts the normal functioning of cancer cells, thereby inhibiting their growth and proliferation.
Furthermore, Chartreusin's potent inhibition of topoisomerase II, an enzyme essential for DNA replication and transcription, contributes to its antitumor activity. This dual mechanism of action makes Chartreusin a valuable compound in the development of cancer treatments.
Used in Drug Development:
In the pharmaceutical industry, Chartreusin is used as an antiproliferative agent for the development of new drugs targeting cancer cells. Its ability to inhibit topoisomerase II makes it a promising candidate for the creation of novel therapeutics that can effectively combat cancer by disrupting essential cellular processes.
Overall, Chartreusin's unique properties and mechanisms of action make it a valuable compound in the fields of oncology and pharmaceutical drug development, with potential applications in the treatment of various types of cancer.

InChI:InChI=1/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3

Upstream product

• 67-56-1 methanol 

Downstream Products

• 34170-23-5 chartarin 

Relevant articles and documents

Molecular Basis for the Final Oxidative Rearrangement Steps in Chartreusin Biosynthesis

Oxidative rearrangements play key roles in introducing structural complexity and biological activities of natural products biosynthesized by type II polyketide synthases (PKSs). Chartreusin (1) is a potent antitumor polyketide that contains a unique rearranged pentacyclic aromatic bilactone aglycone derived from a type II PKS. Herein, we report an unprecedented dioxygenase, ChaP, that catalyzes the final α-pyrone ring formation in 1 biosynthesis using flavin-activated oxygen as an oxidant. The X-ray crystal structures of ChaP and two homologues, docking studies, and site-directed mutagenesis provided insights into the molecular basis of the oxidative rearrangement that involves two successive C-C bond cleavage steps followed by lactonization. ChaP is the first example of a dioxygenase that requires a flavin-activated oxygen as a substrate despite lacking flavin binding sites, and represents a new class in the vicinal oxygen chelate enzyme superfamily.