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Chemical compound
Geldanamycin is a 1,4-benzoquinone ansamycin antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual ADP/ATP-binding pocket of the protein.[1] HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis.[2]
Hsp90-geldanamycin complex. PDB 1yet[3]
Geldanamycin induces the degradation of proteins that are mutated or overexpressed in tumor cells such as v-Src, Bcr-Abl, p53, and ERBB2. This effect is mediated via HSP90. Despite its potent antitumor potential, geldanamycin presents several major drawbacks as a drug candidate such as hepatotoxicity, further, Jilani et al.. reported that geldanamycin induces the apoptosis of erythrocytes under physiological concentrations.[4] These side effects have led to the development of geldanamycin analogues, in particular analogues containing a derivatisation at the 17 position:
17-AAG
17-DMAG
^Schulte, T. W.; Akinaga, S.; Soga, S.; Sullivan, W.; Stensgard, B.; Toft, D.; Neckers, L. M. (1998). "Antibiotic radicicol binds to the N-terminal domain of Hsp90 and shares important biologic activities with geldanamycin". Cell Stress & Chaperones. 3 (2): 100–108. doi:10.1379/1466-1268(1998)003<0100:ARBTTN>2.3.CO;2 (inactive 2024-04-26). PMC 312953. PMID 9672245.{{cite journal}}: CS1 maint: DOI inactive as of April 2024 (link)
^Wayne, N.; Mishra, P.; Bolon, D.N. (2011). "Hsp90 and Client Protein Maturation". Molecular Chaperones. Methods Mol Biol. Vol. 787. pp. 33–44. doi:10.1007/978-1-61779-295-3_3. ISBN 978-1-61779-294-6. PMC 5078872. PMID 21898225.
^Stebbins, C. E.; Russo, A. A.; Schneider, C.; Rosen, N.; Hartl, F. U.; Pavletich, N. P. (1997). "Crystal structure of an Hsp90-geldanamycin complex: Targeting of a protein chaperone by an antitumor agent". Cell. 89 (2): 239–250. doi:10.1016/S0092-8674(00)80203-2. PMID 9108479. S2CID 5253110.
^Jilani, Kashif; Qadri, Syed M.; Lang, Florian (2013). "Geldanamycin-Induced Phosphatidylserine Translocation in the Erythrocyte Membrane". Cell Physiol Biochem. 32 (6): 1600–1609. doi:10.1159/000356596. PMID 24335345.
Geldanamycin is a 1,4-benzoquinone ansamycin antitumor antibiotic that inhibits the function of Hsp90 (Heat Shock Protein 90) by binding to the unusual...
a variety of cancers. Hsp90 inhibitors include the natural products geldanamycin, Retaspimycin hydrochloride (IPI 504, a hydroquinone hydrochloride salt...
azithromycin The antihelminthics ivermectin Ansamycins The antitumor agents geldanamycin and macbecin, The antibiotic rifamycin Polyenes The antifungals amphotericin...
Another variation consists of benzene or a benzoquinone ring system as in geldanamycin or ansamitocin. Ansamycins were first discovered in 1959 by Sensi et...
(17-N-allylamino-17-demethoxygeldanamycin, 17-AAG) is a derivative of the antibiotic geldanamycin that is being studied in the treatment of cancer, specifically in younger...
Beaulieu, Carole (4 March 2017). "Streptomyces cameroonensis sp. nov., a Geldanamycin Producer That Promotes Theobroma cacao Growth". Microbes and Environments...
fungi. These include the cephalosporin producing Acremonium chrysogenum. Geldanamycin is produced by Streptomyces hygroscopicus. Erythromycin is produced by...
Nguyen P, Trepel J, Garcia de Herreros A, et al. (February 2001). "Geldanamycin abrogates ErbB2 association with proteasome-resistant beta-catenin in...
mass transfer. An antibiotic called geldanamycin was separated from media by the capsular perstraction. Geldanamycin is hydrophobic. Outer particle diameter...
it is obtained as a byproduct, or contaminant, at the fermentation of geldanamycin. It is also called polyetherin A, azalomycin M, helixin C, antibiotic...
MutL) superfamily. A common binding pocket for ATP and the inhibitor geldanamycin is situated in the N-terminal domain. Amino acids that are directly involved...
receptor. ORF2 (c-terminal) moderates viral entry by binding to HSC70. Geldanamycin blocks the transport of HEV239 capsid protein, but not the binding/entry...
Streptomyces melanosporofaciens produces elaiophylin, cyclooctatin, geldanamycin, chilaphylin and melanosporin. A mutant of Streptomyces melanosporofaciens...
simultaneously. Small molecule inhibitors, like arsenic trioxide and geldanamycin analogues, have also been identified in downregulating BCR-ABL kinase...
can help prevent rejection after an organ transplant. The antibiotics geldanamycin, hygromycin B, nigericin, validamycin, and cyclothiazomycin are found...
from the genus of Streptomyces. Streptomyces geldanamycininus produces geldanamycin. List of Streptomyces species LPSN bacterio.net Deutsche Sammlung von...
motif at the C-terminus of the HSP. Inhibition of HSP90 activity by geldanamycin derivatives is based on their binding to the ATP binding site. Client...
monocillin II core, but does not have either the epoxide or halogen added. Geldanamycin Zhou H, Qiao K, Gao Z, Vederas JC, Tang Y (2010). "Insights into Radicicol...
these regimens. A recent study showed that blocking Hsp90 function with geldanamycin inhibits PostC protection and PKCε translocation. Additional studies...
of palytoxin, mycolactones, halichondrins, saxitoxin, tetrodotoxin, geldanamycin, batrachotoxin and many others. Kishi has also contributed to the development...
Hartl FU, Pavletich NP (April 1997). "Crystal structure of an Hsp90-geldanamycin complex: targeting of a protein chaperone by an antitumor agent". Cell...
P, Trepel J, Garcia de Herreros A, Dunach M, Neckers LM (Feb 2001). "Geldanamycin abrogates ErbB2 association with proteasome-resistant beta-catenin in...
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