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Merck

H6649

Sigma-Aldrich

Herbimycin A from Streptomyces hygroscopicus

≥95% (HPLC), powder

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About This Item

Fórmula empírica (notación de Hill):
C30H42N2O9
Número de CAS:
Peso molecular:
574.66
Beilstein/REAXYS Number:
4834067
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

Streptomyces hygroscopicus

Quality Level

assay

≥95% (HPLC)

form

powder

color

yellow

solubility

DMSO: 7.5 mg/mL

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CO[C@H]1C[C@H](C)[C@@H](OC)C2=CC(=O)C=C(NC(=O)\C(C)=C\C=C[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@H]1OC)C2=O

InChI

1S/C30H42N2O9/c1-16-10-9-11-23(37-5)28(41-30(31)36)18(3)12-17(2)27(40-8)24(38-6)13-19(4)26(39-7)21-14-20(33)15-22(25(21)34)32-29(16)35/h9-12,14-15,17,19,23-24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b11-9-,16-10+,18-12+/t17-,19-,23-,24-,26+,27+,28-/m0/s1

InChI key

MCAHMSDENAOJFZ-BVXDHVRPSA-N

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General description

DMSO stock solution can be diluted in phosphate buffered saline. The ratio of buffer:DMSO should be greater than 500:1.
Herbimycin A from Streptomyces hygroscopicus is a benzoquinoid ansamycin antibiotic. It is an analog of geldanamycin.

application

Herbimycin A from Streptomyces hygroscopicus has been used as an inhibitor of Src tyrosine kinase in HEK293T cells and rat intestinal epithelial cells. It has also been used to test its attenuation effect in intimal hyperplasia (IH) post balloon injury in rat carotid artery.

Biochem/physiol Actions

Herbimycin A is an inducer of heat shock protein (HSP). It increases HSP expression resulting in the attenuation of ischemia reperfusion induced pulmonary injury.
An antibiotic that inhibits protein tyrosine kinase. Herbimycin A is a potent inhibitor of angiogenesis.

Caution

Hygroscopic and photosensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)


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Visite la Librería de documentos

T Zakar et al.
Canadian journal of physiology and pharmacology, 77(2), 138-142 (1999-10-27)
Human amnion cells in primary culture respond to glucocorticoids in a characteristic fashion by the increased expression of the inducible prostaglandin endoperoxide H synthase isoenzyme, PGHS-2. Since PGHS-2 induction by agonists generally involves tyrosine kinases, we examined the possibility that
Naoki Kawai et al.
Gastroenterology, 122(2), 331-339 (2002-02-08)
Src activation is correlated with progression of colorectal cancer (CRC). CRCs accompanied by ulcerative colitis, chronic inflammation in the colon, often have elevated Src activity, and ulcerative colitis-related CRCs are more likely to become invasive, whereas Ras activation is rarely
T Oikawa et al.
Biological & pharmaceutical bulletin, 17(10), 1430-1432 (1994-10-01)
Six herbimycin A (HBM) derivatives were examined for their anti-angiogenic effects in a bioassay system involving chorioallantoic membranes (CAMs) of growing chick embryos on the basis of our previous observation that HBM is a potent angiogenesis inhibitor. 17-Cyclopropylamino-HBM dose-dependently inhibited
E M Connolly et al.
European journal of vascular and endovascular surgery : the official journal of the European Society for Vascular Surgery, 25(1), 40-47 (2003-01-15)
intimal hyperplasia (IH) is a major cause of re-stenosis post-vascular intervention. Induction of heat shock proteins (HSPs), by thermal pre-conditioning, reduces IH. Our aim was to investigate the effect of the pharmacological HSP inducer herbimycin A on IH in the
Andreas Rascher et al.
Applied and environmental microbiology, 71(8), 4862-4871 (2005-08-09)
Geldanamycin and the closely related herbimycins A, B, and C were the first benzoquinone ansamycins to be extensively studied for their antitumor properties as small-molecule inhibitors of the Hsp90 protein chaperone complex. These compounds are produced by two different Streptomyces

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