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Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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G102383-10mg | 10mg | In stock | $48.90 | |
G102383-50mg | 50mg | In stock | $147.90 | |
G102383-250mg | 250mg | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $666.90 |
Potent fluorescent labelled-HSP90 inhibitor
Synonyms | [(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate | CCG-208040 | HMS1362E15 | [(3S,5S,6R,7S,8E,10R,11S,12Z,14E)-6-Hydroxy-5,11,21-trime |
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Specifications & Purity | Moligand™, ≥98%(HPLC) |
Biochemical and Physiological Mechanisms | Potent fluorescent labelled-HSP90 inhibitor for in vitro and in vivo use. Geldanamycin from Streptomyces hygroscopicus . |
Storage Temp | Store at -20°C |
Shipped In | Ice chest + Ice pads |
Grade | Moligand™ |
Action Type | INHIBITOR |
Mechanism of action | Inhibitor of heat shock protein 90 alpha family class B member 1 |
Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Product Description | λmax 305(MeOH)(Lit.) A benzoquinoid antibiotic that inhibits p60c-src tyrosine kinase and c-myc gene expression in murine lymphoblastoma cells. Geldanamycin has antiproliferative and antitumor effects. Rapidly depletes p185c-erbB2 protein tyrosine kinase in breast carcinoma cells. Binds to HSP90 and disrupts Raf1-HSP90 complex leading to destabilization of Raf1. Inhibits basal and hypoxia-induced expression of c-Jun (IC50 = 75 nM) and abolishes hypoxia-induced increase in c-Jun N-terminal kinase activity. Also known to selectively destabilize mutated p53 protein from a number of breast, leukemia, and prostate cell lines. A benzoquinoid antibiotic that is a potent inhibitor of pp60src tyrosine kinase. Geldanamycin has antiproliferative and antitumor effects. Inhibits basal and hypoxia-induced expression of c-Jun (IC50 = 75 nM) and abolishes hypoxia-induced increase in c-Jun N-terminal Kinase activity. Binds to HSP90 and disrupts raf1-HSP90 complex leading to destabilizing of Raf1. Also destabilizes mutant p53 protein from a number of breast, leukemic, and prostate cell lines. Inhibits c-myc expression in murine lymphoblastoma cells. Approximately ten-fold more potent than herbimycin A |
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Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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IUPAC Name | [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-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 |
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INCHI | InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1 |
InChi Key | QTQAWLPCGQOSGP-KSRBKZBZSA-N |
Canonical SMILES | CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC |
Isomeric SMILES | C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)/C)OC)OC(=O)N)\C)C)O)OC |
WGK Germany | 2 |
RTECS | LX8920000 |
Alternate CAS | 30562-34-6 |
PubChem CID | 5288382 |
MeSH Entry Terms | geldanamycin;geldanomycin |
Molecular Weight | 560.64 |
Reaxy-Rn | 6835113 |
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
Lot Number | Certificate Type | Date | Item |
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L1811146 | Certificate of Analysis | Sep 20, 2022 | G102383 |
Solubility | Soluble in dimethyl sulfoxide at 100 mg/mL. |
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Sensitivity | heat sensitive |
Melt Point(°C) | 255°C |
WGK Germany | 2 |
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RTECS | LX8920000 |
Reaxy-Rn | 6835113 |
1. Xu Yao, Jie Zhu, Lin Li, Bo Yang, Bixia Chen, Endong Bao, Xiaohui Zhang. (2023) Hsp90 protected chicken primary myocardial cells from heat-stress injury by inhibiting oxidative stress and calcium overload in mitochondria. BIOCHEMICAL PHARMACOLOGY, 209 (115434). [PMID:36708886] [10.1016/j.bcp.2023.115434] |
2. Yuanyuan Zhu, Yanyan Huang, Tian-Hao Yan, Jialuo Li, Yongming Li, Hannah F. Drake, Huifei Zhong, Yulong Jin, Rui Zhao, Hong-Cai Zhou. (2022) Metal-Organic Framework-Based Nanoheater with Photo-Triggered Cascade Effects for On-Demand Suppression of Cellular Thermoresistance and Synergistic Cancer Therapy. Advanced Healthcare Materials, 11 (13): (2200004). [PMID:35306753] [10.1002/adhm.202200004] |
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8. Suzanna L Prosser,Kees R Straatman,Andrew M Fry. (2009-01-14) Molecular dissection of the centrosome overduplication pathway in S-phase-arrested cells.. Molecular and cellular biology, 29 ((7)): (1760-1773). [PMID:19139275] |
9. Robert Y L Wang,Rei-Lin Kuo,Wei-Chieh Ma,Hsing-I Huang,Jau-Song Yu,Sih-Min Yen,Chi-Ruei Huang,Shin-Ru Shih. (2013-05-29) Heat shock protein-90-beta facilitates enterovirus 71 viral particles assembly.. Virology, 443 ((2)): (236-247). [PMID:23711381] |
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12. Jana Franke,Simone Eichner,Carsten Zeilinger,Andreas Kirschning. (2013-08-13) Targeting heat-shock-protein 90 (Hsp90) by natural products: geldanamycin, a show case in cancer therapy.. Natural product reports, 30 ((10)): (1299-1323). [PMID:23934201] |
13. Wen-Ying Lee,Yen-Chou Chen,Chwen-Ming Shih,Chun-Mao Lin,Chia-Hsiung Cheng,Ku-Chung Chen,Cheng-Wei Lin. (2013-11-12) The induction of heme oxygenase-1 suppresses heat shock protein 90 and the proliferation of human breast cancer cells through its byproduct carbon monoxide.. Toxicology and applied pharmacology, 274 ((1)): (55-62). [PMID:24211270] |
14. Anna M Leung,Maria J Redlak,Thomas A Miller. (2014-08-26) Role of heat shock proteins in oxygen radical-induced gastric apoptosis.. The Journal of surgical research, 193 ((1)): (135-144). [PMID:25145901] |
15. Tim Jiang,Bona Mu,Rongmin Zhao. (2020-08-28) Plastid chaperone HSP90C guides precursor proteins to the SEC translocase for thylakoid transport.. Journal of experimental botany, 71 ((22)): (7073-7087). [PMID:32853383] |
16. Lena Mancuso,Gerrit Jürjens,Jekaterina Hermane,Kirsten Harmrolfs,Simone Eichner,Jörg Fohrer,Wera Collisi,Florenz Sasse,Andreas Kirschning. (2013-08-29) Bioreduction of aryl azides during mutasynthesis of new ansamitocins.. Organic letters, 15 ((17)): (4442-4445). [PMID:23981134] |
17. Dixian Luo,Yiwen Bu,Jun Ma,Sandeep Rajput,Yingchun He,Guangxian Cai,Duan-Fang Liao,Deliang Cao. (2013-11-13) Heat shock protein 90-α mediates aldo-keto reductase 1B10 (AKR1B10) protein secretion through secretory lysosomes.. The Journal of biological chemistry, 288 ((51)): (36733-36740). [PMID:24217247] |
18. Nagham Asp,Sascha Pust,Kirsten Sandvig. (2014-04-22) Flotillin depletion affects ErbB protein levels in different human breast cancer cells.. Biochimica et biophysica acta, 1843 ((9)): (1987-1996). [PMID:24747692] |
19. Masaki Nagane,Hironobu Yasui,Yuri Sakai,Tohru Yamamori,Koichi Niwa,Yuichi Hattori,Takashi Kondo,Osamu Inanami. (2014-12-17) Activation of eNOS in endothelial cells exposed to ionizing radiation involves components of the DNA damage response pathway.. Biochemical and biophysical research communications, 456 ((1)): (541-546). [PMID:25498542] |
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21. Xu Yao, Jie Zhu, Lin Li, Bo Yang, Bixia Chen, Endong Bao, Xiaohui Zhang. (2023) Hsp90 protected chicken primary myocardial cells from heat-stress injury by inhibiting oxidative stress and calcium overload in mitochondria. BIOCHEMICAL PHARMACOLOGY, 209 (115434). [PMID:36708886] [10.1016/j.bcp.2023.115434] |
22. Yuanyuan Zhu, Yanyan Huang, Tian-Hao Yan, Jialuo Li, Yongming Li, Hannah F. Drake, Huifei Zhong, Yulong Jin, Rui Zhao, Hong-Cai Zhou. (2022) Metal-Organic Framework-Based Nanoheater with Photo-Triggered Cascade Effects for On-Demand Suppression of Cellular Thermoresistance and Synergistic Cancer Therapy. Advanced Healthcare Materials, 11 (13): (2200004). [PMID:35306753] [10.1002/adhm.202200004] |