Geldanamycin from Streptomyces hygroscopicus - ≥98% (HPLC), high purity , CAS No.30562-34-6, Inhibitor of heat shock protein 90 alpha family class B member 1

2 Citations
Item Number
G102383
Grouped product items
SKUSizeAvailabilityPrice Qty
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

Basic Description

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
Specifications & PurityMoligand™, ≥98%(HPLC)
Biochemical and Physiological MechanismsPotent fluorescent labelled-HSP90 inhibitor for in vitro and in vivo use. Geldanamycin from Streptomyces hygroscopicus .
Storage TempStore at -20°C
Shipped InIce chest + Ice pads
GradeMoligand™
Action TypeINHIBITOR
Mechanism of actionInhibitor of heat shock protein 90 alpha family class B member 1
NoteWherever 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

Associated Targets(Human)

TRAP1 Tchem Heat shock protein 75 kDa, mitochondrial (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
HSP90AA1 Tchem Heat shock protein HSP 90-alpha (20 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
HSP90AB1 Tchem Heat shock protein HSP 90-beta (8 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)

Names and Identifiers

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
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

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

1 results found

Lot NumberCertificate TypeDateItem
L1811146Certificate of AnalysisSep 20, 2022 G102383

Chemical and Physical Properties

SolubilitySoluble in dimethyl sulfoxide at 100 mg/mL.
Sensitivityheat sensitive
Melt Point(°C)255°C

Safety and Hazards(GHS)

WGK Germany 2
RTECS LX8920000
Reaxy-Rn 6835113

Related Documents

Citations of This Product

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]
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]

References

1. Zhang C et al..  (2017)  Design, synthesis and pharmacological evaluation of 4,5-diarylisoxazols bearing amino acid residues within the 3-amido motif as potent heat shock protein 90 (Hsp90) inhibitors..  Eur J Med Chem,  125  (315-326).  [PMID:27688186]
2. Geng K et al..  (2018)  Design, synthesis and pharmacological evaluation of ALK and Hsp90 dual inhibitors bearing resorcinol and 2,4-diaminopyrimidine motifs..  Eur J Med Chem,  152  (76-86).  [PMID:29698859]
3. Li Z et al..  (2015)  Discovery of novel 17-phenylethylaminegeldanamycin derivatives as potent Hsp90 inhibitors..  Chem Biol Drug Des,  85  (2): (181-8).  [PMID:24903735]
4. Pan X et al..  (2022)  Discovery of Quinacrine as a Potent Topo II and Hsp90 Dual-Target Inhibitor, Repurposing for Cancer Therapy..  Molecules,  27  (17):   [PMID:36080326]
5. Shabbir A et al..  (2015)  Role of HSP70 in motoneuron survival after excitotoxic stress in a rat spinal cord injury model in vitro..  Eur J Neurosci,  42  (12): (3054-65).  [PMID:26490753]
6. Li Z et al..  (2019)  Synthesis and biological evaluation of geldanamycin-ferulic acid conjugate as a potent Hsp90 inhibitor..  RSC Adv,  (72): (42509-42515).  [PMID:35542888]
7. Lizhen Wang,Chengsong Xie,Elisa Greggio,Loukia Parisiadou,Hoon Shim,Lixin Sun,Jayanth Chandran,Xian Lin,Chen Lai,Wan-Jou Yang,Darren J Moore,Ted M Dawson,Valina L Dawson,Gabriela Chiosis,Mark R Cookson,Huaibin Cai.  (2008-03-28)  The chaperone activity of heat shock protein 90 is critical for maintaining the stability of leucine-rich repeat kinase 2..  The Journal of neuroscience : the official journal of the Society for Neuroscience,  28  ((13)): (3384-3391).  [PMID:18367605]
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]
10. Sailendra Mahanta,Smita Pilla,Subhankar Paul.  (2013-07-19)  Design of novel Geldanamycin analogue hsp90 alpha-inhibitor in silico for breast cancer therapy..  Medical hypotheses,  81  ((3)): (463-469).  [PMID:23860250]
11. Aarif Ahsan,Dipankar Ray,Susmita G Ramanand,Ashok Hegde,Christopher Whitehead,Alnawaz Rehemtulla,Yoshihiro Morishima,William B Pratt,Yoichi Osawa,Theodore S Lawrence,Mukesh K Nyati.  (2013-07-31)  Destabilization of the epidermal growth factor receptor (EGFR) by a peptide that inhibits EGFR binding to heat shock protein 90 and receptor dimerization..  The Journal of biological chemistry,  288  ((37)): (26879-26886).  [PMID:23897823]
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]
20. Chang Hoon Ji,Hee Yeon Kim,Ah Jung Heo,Su Hyun Lee,Min Ju Lee,Su Bin Kim,Ganipisetti Srinivasrao,Su Ran Mun,Hyunjoo Cha-Molstad,Aaron Ciechanover,Cheol Yong Choi,Hee Gu Lee,Bo Yeon Kim,Yong Tae Kwon.  (2019-08-04)  The N-Degron Pathway Mediates ER-phagy..  Molecular cell,  75  ((5)): (1058-1072).  [PMID:31375263]
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]
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]

Solution Calculators