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Geldanamycin

CAS No.
30562-34-6
Chemical Name:
Geldanamycin
Synonyms
GA;Streptomyces hygroscopicus;[(4Z,6E,8R,9R,10Z,12R,13R,14R,16R)-13-Hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaen-9-yl] carbamate;(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21(1)-pentene-3,20,22-trione;CS-503;nsc122750;CP-122634;NSC 212518;Geldamycin;GELDANAMYCIN
CBNumber:
CB8462842
Molecular Formula:
C29H40N2O9
Molecular Weight:
560.64
MDL Number:
MFCD00274570
MOL File:
30562-34-6.mol
MSDS File:
SDS
Last updated:2024-03-19 17:34:45

Geldanamycin Properties

Melting point 255 °C
Boiling point 627.87°C (rough estimate)
Density 1.2443 (rough estimate)
refractive index 1.5800 (estimate)
Flash point 87℃
storage temp. -20°C
solubility DMSO: soluble
form powder
pka 8.42±0.70(Predicted)
color yellow to orange
λmax 305nm(MeOH)(lit.)
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months
CAS DataBase Reference 30562-34-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII Z3K3VJ16KU

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H303-H227
Precautionary statements  P210e-P280a-P370+P378a-P403+P235-P501a
Hazard Codes  T,Xi
Risk Statements  36/37/38
Safety Statements  26-27-36/37/39-24/25
WGK Germany  2
RTECS  LX8920000
HS Code  29419090
NFPA 704
0
1 0

Geldanamycin price More Price(55)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich G3381 Geldanamycin from Streptomyces hygroscopicus ≥98% (HPLC), powder 30562-34-6 1mg $708 2024-03-01 Buy
Sigma-Aldrich 345805 Geldanamycin, Streptomyces hygroscopicus - CAS 30562-34-6 - Calbiochem A benzoquinoid antibiotic that inhibits p60c-src tyrosine kinase and c-myc gene expression in murine lymphoblastoma cells. 30562-34-6 100μg $310 2022-05-15 Buy
TCI Chemical G0334 Geldanamycin >98.0%(HPLC) 30562-34-6 10mg $381 2024-03-01 Buy
Alfa Aesar J63397 Geldanamycin 99+% 30562-34-6 25mg $200 2024-03-01 Buy
Alfa Aesar J67124 Geldanamycin, 1 mg/ml in DMSO, sterile-filtered 30562-34-6 1ml $280 2021-12-16 Buy
Product number Packaging Price Buy
G3381 1mg $708 Buy
345805 100μg $310 Buy
G0334 10mg $381 Buy
J63397 25mg $200 Buy
J67124 1ml $280 Buy

Geldanamycin Chemical Properties,Uses,Production

Description

Geldanamycin from Streptomyces hygroscopicus.
Geldanamycin is a benzoquinone ansamycin antitumor antibiotic. Geldanamycin binds specifically to Hsp90 (Heat Shock Protein 90) and to its endoplasmic reticulum homologue GP96. The Hsp90 chaperone is required for the activation of several families of eukaryotic protein kinases and nuclear hormone receptors, many of which are proto-oncogenic and play a prominent role in cancer. The geldanamycin antibiotic has antiproliferative and antitumor effects, as it binds to Hsp90, inhibits the Hsp90-mediated conformational maturation/refolding reaction, and results in the degradation of Hsp90 substrates. Hsp90 also plays a key role in regulating the physiology of cells exposed to environmental stress and thus, geldanamycin interferes with cellular stress response.
Geldanamycin was found to be a potent antibiotic active at nanomolar concentrations against 60 cell lines as well as in mouse tumor models.
It is an inhibitor of proto-oncogenic protein kinases, such as erbB22, EFG receptor tyrosine kinases, and non-receptor tyrosine kinases, such as v-src and Raf-1. In addition, it is a potent inhibitor of the nuclear hormone receptor family including the estrogen and androgen hormone receptors.

Description

Geldanamycin is a benzoquinone ansamycin antibiotic which binds heat shock protein 90 (Hsp90) and its paralog GRP94, altering their actions. Through its interaction with these chaperones, geldanamycin indirectly affects numerous client proteins with roles in diverse cellular processes, including gene expression, cell proliferation, apoptosis, and angiogenesis. For example, geldanamycin inhibits c-jun expression in human colon adenocarcinoma HT29 cells (IC50 = 75 nM), inhibiting AP-1 binding. It also reduces signaling through mitogenic signaling proteins and interferes with steroid receptor function. Inhibitors of Hsp90, including geldanamycin, show promise in cancer therapy.

Chemical Properties

Yellow to Orange Powder

Uses

Geldanamycin is a potent antitumor antibiotic active at nanomolar concentration against 60 cell lines. It binds specifically to the heat shock protein Hsp90 and to its endoplasmic reticulum homologue GP96, and thus interferes with conformational maturation of proteins and the cellular stress response. In addition, it is a potent inhibitor of the nuclear hormone receptor family.

Uses

Geldanamycin?binds to and inhibits the cytosolic chaperone functions of heat shock protein 90 (HSP90). HSP90 maintains the stability and functional shape of many oncogenic signaling proteins. It interferes with conformational maturation of proteins and the cellular stress response. In addition, it is a potent inhibitor of the nuclear hormone receptor family.

Uses

Geldanamycin is benzoquinone ansamycin antibiotic isolated from Streptomyces hygroscopicus. It is a potent antitumour metabolite that acts by binding to the 90-kDa heat-shock protein (Hsp90) essential to maintain the conformation, stability, activity and cellular localisation of several key oncogenic proteins such as ERBB2, C-RAF, CDK4, AKT/PKB, steroid hormone receptors, mutant p53, HIF-1α, survivin and telomerase hTERT.

Definition

ChEBI: An ansamycin consisting of a 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It shows antimicrobial activity against many Gram-positive and some Gram-negative bacteria.

General Description

Chemical structure: benzenoid

Biological Activity

Selectively inhibits heat shock protein 90 (Hsp90). Binds to the ATP site of Hsp90 (K d = 1.2 μ M) and inhibits its chaperone activity. Consequently inhibits activities of oncogenic kinases (e.g. src, Raf), p53 and steroid receptors.

Biochem/physiol Actions

Primary Targetpc60c-svc tyrosine kinase

storage

+4°C

References

1) Neckers et al. (1999), Geldanamycin as a potential anti-cancer agent: its molecular target and biochemical activity; Invest. New Drugs, 17 361 2) Zang et al. (2006), HSP90 protects apoptotic cleavage of vimentin in geldanamycin-induced apoptosis; Mol. Cell. Biochem., 281 111

75747-28-3
30562-34-6
Synthesis of Geldanamycin from Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

Geldanamycin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 328)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
+8613288715578 sales@hbmojin.com China 12453 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5993 58
Wuhan Xinhao Biotechnology Co., Ltd
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Hebei shuoxi biotechnology co. LTD
+8613081092107 CHINA 968 58

View Lastest Price from Geldanamycin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Geldanamycin pictures 2024-04-02 Geldanamycin
30562-34-6
US $10.00-100.00 / kg 1kg 99% 5000 Metric Ton/Month Wuhan Xinhao Biotechnology Co., Ltd
Geldanamycin pictures 2024-03-16 Geldanamycin
30562-34-6
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Geldanamycin pictures 2023-10-19 Geldanamycin
30562-34-6
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
  • Geldanamycin pictures
  • Geldanamycin
    30562-34-6
  • US $10.00-100.00 / kg
  • 99%
  • Wuhan Xinhao Biotechnology Co., Ltd
  • Geldanamycin pictures
  • Geldanamycin
    30562-34-6
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Geldanamycin pictures
  • Geldanamycin
    30562-34-6
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd

Geldanamycin Spectrum

CP-122634 9,13-Dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione 9-Carbamate NSC 212518 GELDANAMYCIN FROM STRE GeldanaMycin, froM StreptoMyces hygroscopicus var geldanus GeldanaMycin froM StreptoMyces hygroscopi 2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, 9-carbamate Geldanamycin [(3R,5R,6S,7R,8E,10R,11R,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 GeldanamyCln nsc122750 GELDANAMYCIN GELDANAMYCIN, STREPTOMYCES HYGROSCOPICUS 9,13-DIHYDROXY-8,14,19-TRIMETHOXY-4,10,12,16-TETRAMETHYL-2-AZABICYCLO[16.3.1]DOCOSA-4,6,10,18,21-PENTAENE-3,20,22-TRIONE, 9-CARBAMATE GELDANAMYCIN (GDM) GELDANAMYCIN FROM STREPTOMYCES*HYGROSCOP ICUS GELDANAMYCIN, 99+% 2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, 9-carbamate (8CI) [(3R,5R,6S,7R,8E,10R,11R,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 [(8Z,12Z,14Z)-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 Geldanamycin from Streptomyces hygroscopicus, ≥98% (HPLC) geldanamycin 30562-34-6 GELDANAMYCIN;NSC-122750; NSC 122750; NSC122750 Geldanamycin (NSC122750) CS-503 Geldanamycin, Streptomyces hygroscopicus - CAS 30562-34-6 - Calbiochem Geldanamycin, 99%, from Streptomyces hygroscopicus var geldanus, a HSP90 inhibitor Geldanamycin> Geldanamycin Geldanamycin (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 Geldanamycin USP/EP/BP CAS No.30562-34-6 Geldanamycin Geldanamycin (GLD), 98% [(4Z,6E,8R,9R,10Z,12R,13R,14R,16R)-13-Hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaen-9-yl] carbamate (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21(1)-pentene-3,20,22-trione GA Streptomyces hygroscopicus Geldamycin 30562-34-6 562-34-6 0562-34-6 C29H40N2O9 Antibiotics Antibiotics G-M Antibiotics A to Z BioChemical Inhibitors antibiotic Inhibitor Amines Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Heat Shock Protein 90 Antibiotics Antibiotics for Research and Experimental Use Antitumors for Research and Experimental Use Biochemistry Macrolides (Antibiotics for Research and Experimental Use)