70563-58-5

Basic information

• Product Name: HERBIMYCIN A
• Synonyms: antibiotictan420f;herbimycin;HERBIMYCIN A;HERBIMYCIN A, STREPTOMYCES HYGROSCOPICUS;HERBIMYCIN A, STREPTOMYCES SPECIES;herbimycin A from streptomyces hygros-copicus;herbimycin A from streptomyces*hygroscopicus;Herbimycin A, Streptomyces sp.
• CAS NO: 70563-58-5
• Molecular Formula: C30H42N2O9
• Molecular Weight: 574.66
• Product Categories: Heat Shock Protein 90;Antibiotic
• Mol File: 70563-58-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 229-231 °C
• Boiling Point: 752℃
• Flash Point: >110°(230°F)
• Appearance: yellow/powder
• Density: 1.19 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: −20°C
• Solubility: DMSO: 7.5 mg/mL DMSO stock solution can be diluted in phosp
• PKA: 8.56±0.70(Predicted)
• Sensitive: Light Sensitive & Hygroscopic
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• BRN: 4834067
• CAS DataBase Reference: HERBIMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: HERBIMYCIN A(70563-58-5)
• EPA Substance Registry System: HERBIMYCIN A(70563-58-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: LX8930000
• F: 10-21
• Hazardous Substances Data: 70563-58-5(Hazardous Substances Data)

Usage

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

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

Upstream product

• 137788-16-0 (3S,4S,5E,7S,8R,9S,11S)-12<(4-methoxybenzyl)oxy>-3,8,9-trimethoxy-5,7,11-trimethyl-1,5-dodecadien-4-ol 
• 145798-93-2 tert-Butyl-[(E)-(1S,4S,5R,6S,8S)-5,6-dimethoxy-1-((S)-1-methoxy-allyl)-9-(4-methoxy-benzyloxy)-2,4,8-trimethyl-non-2-enyloxy]-dimethyl-silane 
• 1568-70-3 4-methoxy-2-nitrophenol 
• 922166-91-4 ethyl (2E,4Z,6S,7S,8E,10S,11R,12S,14S,15R)-15-[3-bis(tert-butoxycarbonyl)amino-2,5-dimethoxyphenyl]-7-hydroxy-6,11,12,15-tetramethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate 
• 922166-95-8 C₄₃H₇₅NO₁₁Si 
• 922166-88-9 (E)-(3S,4S,7S,8R,9S,11S,12R)-12-[3-bis(tert-butoxycarbonyl)amino-2,5-dimethoxyphenyl]-3,8,9,12-tetramethoxy-5,7,11-trimethyldodeca-1,5-dien-4-yl acrylate 
• 922166-83-4 (E)-(1R,2S,4S,5R,6S,9S,10S)-9-tert-butyldimethylsilyloxy-1-(3-diallylamino-2,5-dimethoxyphenyl)-4,5,10-trimethoxy-2,6,8-trimethyldodec-7,11-dien-1-ol 
• 922166-94-7 (E)-N,N-diallyl-N-{3-[(1R,2S,4S,5R,6S,9S,10S)-9-tert-butyldimethylsilyloxy-1,4,5,10-tetramethoxy-2,6,8-trimethyldodec-7,11-dienyl]-2,5-dimethoxyphenyl}amine 
• 922166-97-0 C₃₈H₆₁NO₁₂ 
• 922166-90-3 C₃₈H₅₉NO₁₂ 
• 922166-96-9 C₃₇H₆₁NO₁₁ 
• 922166-81-2 (E)-(3S,4S,7S,8R,9S,11S)-4-tert-butyldimethylsilyloxy-12-tert-butyldiphenylsilyloxy-3,8,9-trimethoxy-5,7,11-trimethyldodec-1,5-diene 
• 922166-84-5 (E)-N-{3-[(1R,2S,4S,5R,6S,9S,10S)-9-tert-butyldimethylsilyloxy-1,4,5,10-tetramethoxy-2,6,8-trimethyldodec-7,11-dienyl]-2,5-dimethoxyphenyl}amine 
• 922166-93-6 (E)-(3S,4S,7S,8R,9S,11S)-12-tert-butyldiphenylsilyloxy-3,8,9-trimethoxy-5,7,11-trimethyldodec-1,5-dien-4-ol 

Downstream Products

• 91700-92-4 Herbimycin C 
• 1208939-02-9 11-hydroxy-(11-demethoxy)herbimycin C 
• 91700-93-5 C₃₀H₄₄N₂O₉ 

Relevant articles and documents

Total synthesis of herbimycin A

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

Total synthesis of herbimycin A

(Chemical Equation Presented) Hsp90 has recently emerged as a promising biological target for treatment of cancer. Herbimycin A and other members of the benzoquinoid ansamycin class of natural products are known to inhibit Hsp90 activity. The total synthesis of herbimycin A was achieved from the commercially available Roche ester 1 by using allylmetals to control the stereogenic centers at C6, C7, C10, C11, and C12 and a ring-closing metathesis to control the (Z)-double bond of the (E,Z)-dienic moiety.

Gloucose-regulated mRNA instability element

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.

Total Synthesis of Herbimycin A

(Equation presented) Herbimycin A (HA) belongs to a class of antibiotics known as the benzoquinoid ansamycins. Members of this class have shown promising biological activity as Hsp90 inhibitors. An enantioselective synthesis of HA is described, employing

Total synthesis of herbimycin A

The first total synthesis of herbimycin A (1), the benzoquinoid ansamycin antibiotic, has been accomplished by coupling two segments of the aliphatic ansa-chain 2 and the aromatic chromophore 3, elucidating the absolute stereochemistry.