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C2659

Sigma-Aldrich

Chromomycin A₃

from Streptomyces griseus, ≥95% (HPLC), powder, anti-bacterial, anti-fungal and antitumor

Synonym(s):

Aburamycin B, CMA3, NSC 58514

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About This Item

Empirical Formula (Hill Notation):
C57H82O26
CAS Number:
7059-24-7
Molecular Weight:
1183.25
EC Number:
230-348-0
MDL number:
MFCD00043151
UNSPSC Code:
41106305
PubChem Substance ID:
24892514
NACRES:
NA.77

product name

Chromomycin A3 from Streptomyces griseus, ≥95% (HPLC)

Quality Level

200

Assay

≥95% (HPLC)

form

powder

antibiotic activity spectrum

Gram-positive bacteria
fungi
neoplastics

Mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

CO[C@H]1[C@@H](O)CC(O[C@H]1C)O[C@H]2CC(O[C@@H](C)[C@H]2OC(C)=O)Oc3cc4cc5C[C@@H]([C@@H](OC)C(=O)[C@@H](O)[C@H](C)O)[C@H](OC6C[C@@H](OC7C[C@H](OC8C[C@](C)(O)[C@@H](OC(C)=O)[C@H](C)O8)[C@@H](O)[C@H](C)O7)[C@H](O)[C@@H](C)O6)C(=O)c5c(O)c4c(O)c3C

InChI

1S/C57H82O26/c1-21-34(79-40-19-37(53(26(6)75-40)77-28(8)59)82-38-16-33(61)52(70-11)25(5)74-38)15-31-13-30-14-32(54(71-12)51(68)46(63)22(2)58)55(50(67)44(30)49(66)43(31)45(21)62)83-41-18-35(47(64)24(4)73-41)80-39-17-36(48(65)23(3)72-39)81-42-20-57(10,69)56(27(7)76-42)78-29(9)60/h13,15,22-27,32-33,35-42,46-48,52-56,58,61-66,69H,14,16-20H2,1-12H3/t22-,23-,24+,25-,26-,27-,32-,33-,35+,36-,37-,38?,39?,40?,41?,42?,46-,47+,48-,52+,53+,54+,55-,56-,57-/m0/s1

InChI key

ZYVSOIYQKUDENJ-MTPXVABGSA-N

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General description

Chemical structure: aureolic acid

Application

Chromomycin A3 from Streptomyces griseus has been used as a reagent in flow sorting. It has also been used to stain spermatozoa to evaluate the sperm nuclear chromatin integrity.

Biochem/physiol Actions

Chromomycin A3 from Streptomyces griseus is an antibiotic exhibiting anti-bacterial, anti-fungal and antitumor activities. It serves as a fluorescent DNA stain. It is useful for the detection of protamine deficiency in sperm chromatin. The compound blocks macromolecule synthesis by a specific, reversible interaction with DNA in the presence of bivalent metal ions. Binding to DNA minor groove mediates an efficient competitive inhibition of DNA gyrase and significantly affects topoisomerase II activity.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Biosynthesis of the Antitumor Chromomycin A3 in Streptomyces griseus: Analysis of the Gene Cluster and Rational Design of Novel Chromomycin Analogs
Menendez, N et al.
Chemistry and Biology, 11(2), 21-32 (2019)
Strategies for choosing a deoxyribonucleic acid stain for flow cytometry of metaphase chromosomes.
Jensen R, et al.
The Journal of Histochemistry and Cytochemistry, 25(8), 954-964 (1977)
S Chakrabarti et al.
Biochemical pharmacology, 56(11), 1471-1479 (1998-11-25)
Chromomycin A3 (CHR), an anticancer antibiotic, blocks macromolecular synthesis via reversible interaction with DNA only in the presence of divalent cations like Mg2+. In the absence of DNA, the antibiotic forms a dimer: Mg2+ complex [(CHR)2Mg2+]. It is the DNA-binding
Dietary supplementation with astaxanthin may ameliorate sperm parameters and DNA integrity in streptozotocin-induced diabetic rats
Menendez, N et al.
Clinical and Experimental Reproductive Medicine, 43(2), 90-96 (2016)
A Bell et al.
Journal of molecular recognition : JMR, 10(6), 245-255 (1998-10-15)
We present titrations of the human delta beta-globin gene region with DNA minor groove binders netropsin, bisnetropsin, distamycin, chromomycin and four bis-quaternary ammonium compounds in the presence of calf thymus topoisomerase II and DNase I. With increasing ligand concentration, stimulation
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