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Geldanamycin

Product Name
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;CP-122634;nsc122750;NSC 212518;Geldamycin;GeldanamyCln
CBNumber
CB8462842
Molecular Formula
C29H40N2O9
Formula Weight
560.64
MOL File
30562-34-6.mol
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Geldanamycin Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H227Combustible liquid

H303May be harmfulif swallowed

Precautionary statements

P403+P235Store in a well-ventilated place. Keep cool.

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N-Bromosuccinimide Price

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

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.

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

Geldanamycin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Geldanamycin manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Geldanamycin 30562-34-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-31
Hebei Yanxi Chemical Co., Ltd.
Product
Geldanamycin 30562-34-6
Price
US $20.00-1.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
30 tons
Release date
2023-10-08
Wuhan Xinhao Biotechnology Co., Ltd
Product
Geldanamycin 30562-34-6
Price
US $10.00-100.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000 Metric Ton/Month
Release date
2024-03-19

30562-34-6, GeldanamycinRelated Search:

CHLOROPHOSPHONAZO III p-Toluquinone 17-Demethoxy-17-[[2-(dimethylamino)ethyl]amino]geldanamycin 17-AAG Retaspimycin 17-Amino Geldanamycin 17-DIMETHYLAMINOETHYLAMINO-17-DEMETHOXY-GELDANAMYCIN 17-Amino Geldanamycin-13C,15N2 3-HEXENE-1 6-DIOLE 2-METHOXY-3-METHYL-[1,4]BENZOQUINONE 2-methoxyethyl carbamate herbimycin B N-DECYL ACRYLAMIDE N-DECYL METHACRYLAMIDE 17-Demethoxy-17-(allylamino-d5)geldanamycin,17-(Allylamino-d5) Geldanamycin,17-Demethoxy-17-(2-propenylamino-d5)geldanamycin Geldanamycin GELDANAMYCIN 95% 17-DESMETHOXY-17-N,N-DIMETHYLAMINOETHYLAMINO-GELDANAMYCIN, HCL,17-N,N-DIMETHYLAMINOETHYLAMINO-17-DEMETHOXY-GELDANAMYCIN, HCL

  • 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
  • [(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
  • 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
  • Geldanamycin, 99%, from Streptomyces hygroscopicus var geldanus, a HSP90 inhibitor
  • nsc122750
  • GELDANAMYCIN
  • GELDANAMYCIN, STREPTOMYCES HYGROSCOPICUS
  • GA
  • 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+%
  • Streptomyces hygroscopicus
  • 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&gt
  • 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%
  • Geldamycin
  • Geldanamycin, Hsp90 inhibitor
  • Geldanamycin-FITC, fluorescent labelled HSP90 inhibitor
  • 30562-34-6
  • 0562-34-6
  • 562-34-6
  • C29H40N2O9
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