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C2659

Sigma-Aldrich

Chromomycin A₃

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

Synonym(e):

Aburamycin B, CMA3, NSC 58514

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About This Item

Empirische Formel (Hill-System):
C57H82O26
CAS-Nummer:
7059-24-7
Molekulargewicht:
1183.25
EG-Nummer:
230-348-0
MDL-Nummer:
MFCD00043151
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24892514
NACRES:
NA.77

product name

Chromomycin A3, ≥95% (HPLC)

Qualitätsniveau

200

Assay

≥95% (HPLC)

Form

powder

Wirkungsspektrum von Antibiotika

Gram-positive bacteria
fungi
neoplastics

Wirkungsweise

DNA synthesis | interferes

Lagertemp.

−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

InChIKey

ZYVSOIYQKUDENJ-MTPXVABGSA-N

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Allgemeine Beschreibung

Chemical structure: aureolic acid

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H300

Gefahreneinstufungen

Acute Tox. 1 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Analysenzertifikate (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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H Simon et al.
FEBS letters, 353(1), 79-83 (1994-10-10)
The influence of netropsin (Nt), distamycin A (Dst-3) and chromomycin A3 (CHR) on the binding of gyrase from Streptomyces noursei to an 162 bp-fragment of pBR 322 containing a strong gyrase cleavage site and on the gyrase mediated cleavage of
Phylogenomic analysis by chromosome sorting and painting
Stanyon R, et al.
Methods in Molecular Biology, 13-29 (2008)
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
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)
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)
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