70563-58-5 Usage
Description
Herbimycin A, an ansamycin antibiotic, is a potent inhibitor of protein tyrosine kinases and the heat shock protein Hsp90. It is derived from a complex of benzoquinone ansamycin antibiotics isolated from Streptomyces hygroscopicus. Herbimycin A exhibits antitumor effects, induces apoptosis, and inhibits angiogenesis. It also reverts tyrosine kinase-induced oncogenic transformation without directly inhibiting phosphorylation activity.
Uses
Used in Pharmaceutical Industry:
Herbimycin A is used as an inhibitor for various protein tyrosine kinases, including c-Abl, HSP 90, c-Src, c-Yes, Fes, and Ros. It is particularly effective against Bcr-Abl with an IC50 value of 5 μM, which also effectively blocks Src, Yes, Fps, Ros, and ErbB. It is also a COVID-19-related research product.
Used in Cancer Research and Treatment:
Herbimycin A is used as an anticancer agent, targeting various oncogenic signaling pathways and exhibiting synergistic effects when combined with conventional chemotherapeutic drugs. It induces apoptosis and inhibits angiogenesis, making it a promising candidate for cancer treatment.
Used in Drug Delivery Systems:
Herbimycin A is used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for Herbimycin A delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Used in Research Applications:
Herbimycin A is used as a research tool to study the effects of inhibiting protein tyrosine kinases and Hsp90 on cellular processes, including cell transformation, angiogenesis, and apoptosis. It is also used to investigate the destabilization of client proteins, such as Src, Bcr-Abl, and ErbB2, leading to their ubiquitination and proteasomal degradation.
Biological Activity
Ansamycin antibiotic that acts as a Src family kinase inhibitor. Binds to the SH domain and inhibits the activity of p60 v-src and p210 BCR-ABL . Exhibits antiangiogenic activity in endothelial cells in vitro . Also inhibits Hsp90 and impairs recovery from heat shock.
Biochem/physiol Actions
Cell permeable: yes
References
1) Whitesell et al. (1994), Inhibition of heat shock protein HSP-90-pp60vsrc heteroprotein complex formation by benzoquinone ansamycins: essential role for stress proteins in oncogenic transformation; Proc. Natl. Acad. Sci. USA, 91 8324
2) Blagosklonny et al. (2002), Hsp-90-associated oncoproteins: multiple targets of geldanamycin and it’s analogs; Leukemia, 16 455
3) GW McCollum et al. (2004), Herbimycin A inhibits angiogenic activity in endothelial cells and reduces neovascularization in a rat model of retinopathy of prematurity; Exp. Eye Res., 78 987
Check Digit Verification of cas no
The CAS Registry Mumber 70563-58-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,0,5,6 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 70563-58:
(7*7)+(6*0)+(5*5)+(4*6)+(3*3)+(2*5)+(1*8)=125
125 % 10 = 5
So 70563-58-5 is a valid CAS Registry Number.
InChI:InChI=1/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
70563-58-5Relevant articles and documents
Total synthesis of herbimycin A
Yan, Rui,Bian, Chuancai,Yu, Xiaoming
supporting information, p. 3280 - 3283 (2014/07/08)
Benzoquinone ansamycin antibiotic herbimycin A was synthesized in 19 linear steps and 4.2% yield. Highlighted is the design of a chiral γ-lactone as the C11-C15 synthon that enabled a facile catalytic asymmetric synthesis of the challenging C8-C20 fragmen
Gloucose-regulated mRNA instability element
-
, (2008/06/13)
The subject invention pertains to nucleic acid constructs for post-transcriptional control of expression of a ploynucleotide encoding a protein in a eukaryotic cell, wherein the constructs include a metabolite responsive instability element such as the glucose-regulated mRNA instability element. The subject invention further pertains to host cells and vectors comprising the nucleic acid constructs of the invention, as well as probes, methods, and kits for detecting metabolite responsive instability elements or mutations thereof.
The total synthesis of herbimycin A
Nakata,Osumi,Ueno,Kimura,Tamai,Tatsuta
, p. 2974 - 2991 (2007/10/02)
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