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Merck
CN

C2659

Chromomycin A₃

from Streptomyces griseus, ≥95% (HPLC), powder, RNA synthesis inhibitor

别名:

Aburamycin B, CMA3, NSC 58514

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关于此项目

经验公式（希尔记法）:
C57H82O26
化学文摘社编号:
7059-24-7
分子量:
1183.25
UNSPSC Code:
41106305
PubChem Substance ID:
24892514
NACRES:
NA.77
EC Number:
230-348-0
MDL number:
MFCD00043151

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产品名称

色霉素A3 来源于灰色链霉菌, ≥95% (HPLC)

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

assay

≥95% (HPLC)

form

powder

antibiotic activity spectrum

Gram-positive bacteria, fungi, neoplastics

mode of action

DNA synthesis | interferes

storage temp.

−20°C

Quality Level

200

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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

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 1 Oral

存储类别

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

ppe

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

法规信息

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分析证书(COA)

Lot/Batch Number
0000486095
0000486095
0000458754
0000458753
0000458754

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Phylogenomic analysis by chromosome sorting and painting
Stanyon R, et al.
Methods in Molecular Biology, 13-29 (2008)
Gry Brandt Boe-Hansen et al.
Molecular reproduction and development, 87(5), 574-597 (2020-02-23)
Environmental temperature has effects on sperm quality with differences in susceptibility between cattle subspecies and breeds, but very little is known about the seminal plasma protein (SPP) changes resulting from testicular heat stress. Scrotal insulation (SI) for 48 hr was applied
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
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
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
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