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Merck

C9270

Sigma-Aldrich

Coumermycin A1

Synonym(e):

Notomycin A1

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About This Item

Empirische Formel (Hill-System):
C55H59N5O20
CAS-Nummer:
Molekulargewicht:
1110.08
Beilstein:
470805
MDL-Nummer:
UNSPSC-Code:
51102829
PubChem Substanz-ID:
NACRES:
NA.85

Form

powder

Löslichkeit

DMSO: 50 mg/mL

Wirkungsspektrum von Antibiotika

Gram-negative bacteria
Gram-positive bacteria

Wirkungsweise

DNA synthesis | interferes
enzyme | inhibits

SMILES String

CO[C@@H]1[C@@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc3ccc4C(O)=C(NC(=O)c5c[nH]c(C(=O)NC6=C(O)c7ccc(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)c9ccc(C)[nH]9)[C@H]8O)c(C)c7OC6=O)c5C)C(=O)Oc4c3C)OC1(C)C

InChI

1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

InChIKey

WTIJXIZOODAMJT-DHFGXMAYSA-N

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Allgemeine Beschreibung

Chemical structure: coumarin-glycoside

Anwendung

Coumermycin A1 is an aminocoumarin antibiotic used to study processes such as DNA replication, transcription, and recombination that involve DNA topoisomerase II activity. It has been used to treat Staphylococcus aureus endocarditis in the rat model and to study the effect of coumermycin A1 on the expression of 67 fusions in Salmonella typhimurium. .

Biochem./physiol. Wirkung

Coumermycin A1 inhibits DNA Gyrase which thereby inhibits cell division in bacteria.

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


Analysenzertifikate (COA)

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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

S B Jovanovich et al.
Journal of bacteriology, 169(10), 4431-4435 (1987-10-01)
We have estimated the extent to which relaxation of supercoiling by the DNA gyrase inhibitor coumermycin A1 affects gene expression in vivo in Salmonella typhimurium. We isolated a set of Mu d1-8 Lac+ operon fusions to random promoters and measured
Joseph A Burlison et al.
Organic letters, 8(21), 4855-4858 (2006-10-06)
[structure: see text] The coumarin antibiotics are not only potent inhibitors of DNA gyrase but also represent the most effective C-terminal inhibitors of 90 kDa heat shock proteins (Hsp90) reported thus far. In contrast to the N-terminal ATP-binding site, little
Ryan C Chai et al.
Molecular oncology, 11(5), 567-583 (2017-03-18)
Heat shock protein 90 (HSP90) regulates multiple signalling pathways critical for tumour growth. As such, HSP90 inhibitors have been shown to act as effective anticancer agents in preclinical studies but, for a number of reasons, the same effect has not
C M Perronne et al.
Antimicrobial agents and chemotherapy, 31(4), 539-543 (1987-04-01)
The efficacy of a 5-day treatment with coumermycin A1 (hereafter referred to as coumermycin) (at three dosage regimens), with ciprofloxacin, or with coumermycin plus ciprofloxacin was tested in experimental aortic valve endocarditis induced in rats by a strain of methicillin-susceptible
Lutz Heide
Methods in enzymology, 459, 437-455 (2009-04-14)
The aminocoumarin antibiotics novobiocin, clorobiocin and coumermycin A(1) are formed by different Streptomyces strains and are potent inhibitors of bacterial gyrase. Their biosynthetic gene clusters have been analyzed in detail by genetic and biochemical investigations. Heterologous expression of these gene

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