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Chromomycin A3

Chromomycin A3 structure

CAS No:
7059-24-7
Formula:
C57H82O26
Chemical Name:
Chromomycin A3
Synonyms:
D-threo-2-Pentulose,1-C-[(2S,3S)-7-[[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy]-3-[[O-4-O-acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-5-deoxy-1-O-methyl-,(1S)-;Olivomycin D,3D-O-(4-O-acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl)-7-methyl-;Chromomycin A3;(1S)-1-C-[(2S,3S)-7-[[4-O-Acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy]-3-[[O-4-O-acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-5-deoxy-1-O-methyl-D-threo-2-pentulose;Toyomycin;Aburamycin B;Antibiotic B 599;CMA3;NSC 58514;1409-52-5;7261-09-8;11023-62-4;14711-93-4;20056-86-4
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Chromomycin A3 is an aureolic acid-type antitumor antibiotic. Chromomycin A3 forms dimeric complexes with divalent cations, such as Mg2+, which strongly binds to the GC rich sequence of DNA to inhibit DNA replication and transcription. Chromomycin A3 has a variety of utilities as a staining agent for human sperm chromatin, autophagy inducing agent, and apoptosis inhibitor[1].

Chromomycin A3 is a chromomycin.|Chromomycin A3 is a glycosidic antineoplastic antibiotic isolated from the bacterium Streptomyces griseus. Chromomycin A3 reversibly binds to guanine-cytosine (G-C) base pairs in the minor groove of DNA, thereby inhibiting RNA synthesis. This agent is used as a fluorescent chromosome dye. (NCI04)|Glycosidic antibiotic from Streptomyces griseus used as a fluorescent stain of DNA and as an antineoplastic agent.

Chromomycin A3 Basic Attributes

Molecular Weight：

1183.25

Exact Mass：

1183.25

EC Number：

230-348-0

UNII：

DVW027E7NL

DSSTox ID：

DTXSID4046363

NCI Thesaurus Code：

C895

HScode：

29419090

Characteristics

PSA：

359.34000

XLogP3：

1.54640

Density：

1.43g/cm3

Melting Point：

185 °C (decomp)

Boiling Point：

1147.6ºC at 760 mmHg

Flash Point：

311.1ºC

Refractive Index：

1.608

Water Solubility：

soluble in ethanol, DMSO, and ethyl acetate (10 mg/ml).

Storage Conditions：

2-8°C

Toxicity：

Excitation max: ~445 nm. Emission max: ~575 nm. Sol in ethanol, ethyl acetate, DMSO, methanol. LD50 in mice (mg/kg): 1.85 i.v. (Slavik, Carter).

Specific rotation：

D23 -57° (ethanol)

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

UN 3462 6.1/PG 1

wgk germany：

hazard class code：

61-28

safety instructions：

53-28-36/37/39-45

RTECS Number：

GB7875000

Marks：

T+,T

Precautionary statement(s)：

P201-P264-P301 + P310-P308 + P313

Hazard Statements：

H300-H360

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P310, P308+P313, P321, P330, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)|Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

MeSH Entry Terms：

Chromomycin A3

Chromomycin A3 Use and Manufacturing

Fluorescent DNA stain in flow cytometry and karyotype analysis of chromosomes.

Computed Properties

Molecular Weight:1183.2
XLogP3:2.3
Hydrogen Bond Donor Count:8
Hydrogen Bond Acceptor Count:26
Rotatable Bond Count:20
Exact Mass:1182.50943272
Monoisotopic Mass:1182.50943272
Topological Polar Surface Area:359
Heavy Atom Count:83
Complexity:2190
Defined Atom Stereocenter Count:25
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes