An inhibitor of tyrosine kinases and Hsp90
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Herbimycin A

Item No. 15504

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
17-demethoxy-15R-methoxy-11-O-methyl-geldanamycin
CAS Number
70563-58-5
Synonyms
  • Antibiotic TAN 420F
  • NSC 305978
Molecular Formula
C30H42N2O9
Formula Weight
574.7
Purity
≥95%
Formulation (Request formulation change)
A yellow lyophilisate
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O=C(C=C(C1=O)NC(/C(C)=C/C=C\[C@H](OC)[C@@H](OC(N)=O)/C(C)=C/[C@@H]([C@H]([C@H](C[C@@H]2C)OC)OC)C)=O)C=C1[C@@H]2OC
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+,2
InChi Key
MCAHMSDENAOJFZ-BVXDHVRPSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $418

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    2.5 mg

    $1,355

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    Product Description

    Herbimycin A is a benzoquinone ansamycin antibiotic from Streptomyces.1 It has herbicidal activity and acts as a cell-permeable inhibitor of non-receptor tyrosine kinases and the heat shock protein Hsp90.1,2,3 Herbimycin A inhibits Bcr-Abl with an IC50 value of 5 μM, a concentration that also effectively blocks Src, Yes, Fps, Ros, and ErbB but not protein kinases (PK) PKA, PKC, Rac, Myc, or Raf.2,4 Presumably through its effects on tyrosine kinase signaling, herbimycin A also impairs endothelial cell proliferation in the context of angiogenesis, NF-κB activation, phosphorylation of phospholipase C-γ1, and eggshell formation in schistosome parasites.5,6,7,8 Ansamycins, including herbimycin A and geldanamycin (Item No. 13355), bind Hsp90 and destabilize client proteins, including Src, Bcr-Abl, and ErbB2, leading to their ubiquitination and proteasomal degradation.3,9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Omura, S., Iwai, Y., Takahashi, Y., et al. Herbimycin, a new antibiotic produced by a strain of Streptomyces. J. Antibiot. (Tokyo) 32(4), 255-261 (1979).

    2. Uehara, Y., and Fukazawa, H. Use and selectivity of herbimycin A as inhibitor of protein-tyrosine kinases. Methods Enzymol. 201, 371-379 (1991).

    3. Blagosklonny, M.V. Hsp-90-associated oncoproteins: Multiple targets of geldanamycin and its analogs. Leukemia 16(4), 455-462 (2002).

    4. Fukazawa, H., Li, P.M., Yamamoto, C., et al. Specific inhibition of cytoplasmic protein tyrosine kinases by herbimycin A in vitro. Biochem. Pharmacol. 42(9), 1661-1671 (1991).

    5. Fan, T.P.D., Jaggar, R., and Bicknell, R. Controlling the vasculature: Angiogenesis, anti-angiogenesis and vascular targeting of gene therapy. Trends Pharmacol. Sci. 16(2), 57-66 (1995).

    6. Ogina, S., Tsuruma, K., Uehara, T., et al. Herbimycin A abrogates nuclear factor-κB activation by interacting preferentially with the IκB kinase β subunit. Mol. Pharmacol. 65(6), 1344-1351 (2004).

    7. Park, D.J., Min, H.K., and Rhee, S.G. IgE-induced tyrosine phosphorylation of phospholipase C-γ1 in rat basophilic leukemia cells. The Journal of Biological Chemisty 266(36), 24237-24240 (1991).

    8. Buro, C., Oliveira, K.C., Lu, Z., et al. Transcriptome analyses of inhibitor-treated schistosome females provide evidence for cooperating Src-kinase and TGFβ receptor pathways controlling mitosis and eggshell formation. PLoS Pathog. 9(6), e1003448 (2013).

    9. Whitesell, L., Mimnaugh, E.G., De Costa, B., et al. Inhibition of heat shock protein Hsp90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: Essential role for stress proteins in oncogenic transformation. Proc. Natl. Acad. Sci. USA 91(18), 8324-8328 (1994).