Herbimycin | CAS#70563-58-5 | HSP90 inhibitor | PKC inhibitor | Src inhibitor | Bcr-Abl inhibitor

MedKoo Cat#: 540192 | Name: Herbimycin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Herbimycin is an inhibitor of HSP90, PKC, Src and Bcr-Abl. It inhibits proliferation of chronic myelogenous leukemia cells.

Chemical Structure

Herbimycin

CAS#70563-58-5

Theoretical Analysis

MedKoo Cat#: 540192

Name: Herbimycin

CAS#: 70563-58-5

Chemical Formula: C30H42N2O9

Exact Mass: 574.2890

Molecular Weight: 574.67

Elemental Analysis: C, 62.70; H, 7.37; N, 4.87; O, 25.06

Price and Availability

Size	Price	Availability	Quantity
500µg	USD 685.00	2 Weeks

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Related CAS #

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Synonym

Antibiotic Tan 420F; Herbimycin; Herbimycin A; NSC 305978; NSC305978; NSC-305978

IUPAC/Chemical Name

(4E,6E,8S,9S,10E,12S,13R,14S,16S,17R)-8,13,14,17-tetramethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate

InChi Key

MCAHMSDENAOJFZ-GDYSMBPZSA-N

InChi Code

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

SMILES Code

C[C@H]1C[C@H](OC)[C@H](OC)[C@@H](C)/C=C(C)/[C@H](OC(N)=O)[C@@H](OC)/C=C/C=C(C)/C(NC2=CC(C=C(C2=O)[C@@H]1OC)=O)=O

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 574.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Yan R, Bian C, Yu X. Total synthesis of herbimycin A. Org Lett. 2014 Jun 20;16(12):3280-3. doi: 10.1021/ol5012899. Epub 2014 Jun 9. PubMed PMID: 24911938. 2: Zhao W, Jiang B, Wu L, Nan Y, Cui J, Yu L, Wei Y, Li J, Shan G. Two herbimycin analogs, 4,5-dihydro-(4S)-4-hydroxyherbimycin B and (15S)-15-hydroxyherbimycin B, from Streptomyces sp. CPCC 200291. J Antibiot (Tokyo). 2015 Jul;68(7):476-80. doi: 10.1038/ja.2015.12. Epub 2015 Feb 18. PubMed PMID: 25690359. 3: Kim SH, Kang JG, Kim CS, Ihm SH, Choi MG, Yoo HJ, Lee SJ. 17-Allylamino-17-demethoxygeldanamycin and Herbimycin A Induce Cell Death by Modulating β-Catenin and PI3K/AKT Signaling in FRO Anaplastic Thyroid Carcinoma Cells. Anticancer Res. 2015 Oct;35(10):5453-60. PubMed PMID: 26408708. 4: Kim SH, Kang JG, Kim CS, Ihm SH, Choi MG, Yoo HJ, Lee SJ. Herbimycin A inhibits cell growth with reversal of epithelial-mesenchymal transition in anaplastic thyroid carcinoma cells. Biochem Biophys Res Commun. 2014 Dec 12;455(3-4):363-70. doi: 10.1016/j.bbrc.2014.11.018. Epub 2014 Nov 15. PubMed PMID: 25446094. 5: Cabral-da-Silva MC, dos Santos NE, de Mello FG, Taylor JS, Tolkovsky AM, Linden R, Reis RA. Herbimycin A induces sympathetic neuron survival and protects against hypoxia. Neuroreport. 2003 Dec 19;14(18):2397-401. PubMed PMID: 14663199. 6: Murakami Y, Mizuno S, Hori M, Uehara Y. Reversal of transformed phenotypes by herbimycin A in src oncogene expressed rat fibroblasts. Cancer Res. 1988 Mar 15;48(6):1587-90. PubMed PMID: 3345529. 7: Hamel L, Kenney M, Jayyosi Z, Ardati A, Clark K, Spada A, Zilberstein A, Perrone M, Kaplow J, Merkel L, Rojas C. Induction of heat shock protein 70 by herbimycin A and cyclopentenone prostaglandins in smooth muscle cells. Cell Stress Chaperones. 2000 Apr;5(2):121-31. PubMed PMID: 11147963; PubMed Central PMCID: PMC312898. 8: Sachidhanandam SB, Lu J, Low KS, Moochhala SM. Herbimycin A attenuates apoptosis during heat stress in rats. Eur J Pharmacol. 2003 Aug 1;474(1):121-8. PubMed PMID: 12909203. 9: Briant D, Ohan N, Heikkila JJ. Effect of herbimycin A on hsp30 and hsp70 heat shock protein gene expression in Xenopus cultured cells. Biochem Cell Biol. 1997;75(6):777-82. PubMed PMID: 9599667. 10: Tsuji A, Asano T, Suzuki S, Aoyagi T, Hayakawa M, Nakamura H. Effect of herbimycin A on renal cancer cell growth. Nihon Jinzo Gakkai Shi. 1996 May;38(5):198-201. PubMed PMID: 8699609. 11: Kiang JG. Genistein inhibits herbimycin A-induced over-expression of inducible heat shock protein 70 kDa. Mol Cell Biochem. 2003 Mar;245(1-2):191-9. PubMed PMID: 12708759. 12: Iwai Y, Nakagawa A, Sadakane N, Omura S, Oiwa H, Matsumoto S, Takahashi M, Ikai T, Ochiai Y. Herbimycin B, a new benzoquinonoid ansamycin with anti-TMV and herbicidal activities. J Antibiot (Tokyo). 1980 Oct;33(10):1114-9. PubMed PMID: 7451361. 13: Sato S, Honma Y, Hozumi M, Hayashi Y, Matsuo Y, Shibata K, Omura S, Hino K, Tomoyasu S, Tsuruoka N. Effects of herbimycin A and its derivatives on growth and differentiation of Ph1-positive acute lymphoid leukemia cell lines. Leuk Res. 1994 Mar;18(3):221-8. PubMed PMID: 8139288. 14: Preis PN, Saya H, Nádasdi L, Hochhaus G, Levin V, Sadée W. Neuronal cell differentiation of human neuroblastoma cells by retinoic acid plus herbimycin A. Cancer Res. 1988 Nov 15;48(22):6530-4. PubMed PMID: 2846152. 15: Honma Y, Okabe-Kado J, Hozumi M, Uehara Y, Mizuno S. Induction of erythroid differentiation of K562 human leukemic cells by herbimycin A, an inhibitor of tyrosine kinase activity. Cancer Res. 1989 Jan 15;49(2):331-4. PubMed PMID: 2910452. 16: Sepp-Lorenzino L, Ma Z, Lebwohl DE, Vinitsky A, Rosen N. Herbimycin A induces the 20 S proteasome- and ubiquitin-dependent degradation of receptor tyrosine kinases. J Biol Chem. 1995 Jul 14;270(28):16580-7. PubMed PMID: 7622464. 17: Queiroz CM, Mello LE. Effects of herbimycin A in the pilocarpine model of temporal lobe epilepsy. Brain Res. 2006 Apr 7;1081(1):219-27. PubMed PMID: 16696126. 18: Endo N, Tashiro E, Umezawa K, Kawada M, Uehara Y, Doki Y, Weinstein IB, Imoto M. Herbimycin A induces G1 arrest through accumulation of p27(Kip1) in cyclin D1-overexpressing fibroblasts. Biochem Biophys Res Commun. 2000 Jan 7;267(1):54-8. PubMed PMID: 10623573. 19: Makishima M, Yamamoto-Yamaguchi Y, Honma Y. 19-Allylaminoherbimycin A, an analog of herbimycin A that is stable against treatment with thiol compounds or granulocyte-macrophage colony-stimulating factor in human leukemia cells. Biochim Biophys Acta. 1995 Dec 12;1272(3):199-205. PubMed PMID: 8541353. 20: Suzukake-Tsuchiya K, Moriya Y, Hori M, Uehara Y, Takeuchi T. Induction by herbimycin A of contact inhibition in v-src-expressed cells. J Antibiot (Tokyo). 1989 Dec;42(12):1831-7. PubMed PMID: 2559910.

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