Geldanamycin
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MedKoo CAT#: 205922

CAS#: 30562-34-6

Description: Geldanamycin is a benzoquinone ansamycin antibiotic that binds to Hsp90 (Heat Shock Protein 90) and inhibits its function. HSP90 client proteins play important roles in the regulation of the cell cycle, cell growth, cell survival, apoptosis, angiogenesis and oncogenesis. Hsp90-geldanamycin complex. PDB 1yet Geldanamycin induces the degradation of proteins that are mutated in tumor cells such as v-Src, Bcr-Abl and p53 preferentially over their normal cellular counterparts. This effect is mediated via HSP90. Despite its potent antitumor potential, geldanamycin presents several major drawbacks as a drug candidate (namely, hepatotoxicity) that have led to the development of geldanamycin analogues.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 750
Size
Price

25mg
USD 250
200mg
USD 1250
Size
Price

50mg
USD 450

Geldanamycin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205922
Name: Geldanamycin
CAS#: 30562-34-6
Chemical Formula: C29H40N2O9
Exact Mass: 560.27338
Molecular Weight: 560.6359
Elemental Analysis: C, 62.13; H, 7.19; N, 5.00; O, 25.68


Synonym: NSC 122750; NSC-122750; NSC122750; U 29135; U-29135; U29135. Geldanamycin.

IUPAC/Chemical 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 Key: QTQAWLPCGQOSGP-KSRBKZBZSA-N

InChi Code: 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

SMILES Code: NC(O[C@@H](/C(C)=C/[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC1=C2OC)[C@@H](OC)/C=C\C=C(C)\C(NC(C1=O)=CC2=O)=O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Geldanamycin was originally discovered in the organism Streptomyces hygroscopicus. It is a macrocyclic polyketide that is synthesized by a Type I polyketide synthase. The genes gelA, gelB, and gelC encode for the polyketide synthase. The PKS is first loaded with 3-amino-5-hydroxybenzoic acid (AHBA). It then utilizes malonyl-CoA, methylmalonyl-CoA, and methoxymalonyl-CoA to synthesize the precursor molecule Progeldanamycin.   This precursor is subjected to several enzymatic and non-enzymatic tailoring steps to produce the active molecule Geldanamycin, which include hydroxylation, o-methylation, carbamoylation, and oxidation.   
 
 
 


References

1: Gorska M, Popowska U, Sielicka-Dudzin A, Kuban-Jankowska A, Sawczuk W, Knap N, Cicero G, Wozniak F. Geldanamycin and its derivatives as Hsp90 inhibitors. Front Biosci. 2012 Jun 1;17:2269-77. Review. PubMed PMID: 22652777.

2: Fukuyo Y, Hunt CR, Horikoshi N. Geldanamycin and its anti-cancer activities. Cancer Lett. 2010 Apr 1;290(1):24-35. Epub 2009 Oct 21. Review. PubMed PMID: 19850405.

3: Hadden MK, Lubbers DJ, Blagg BS. Geldanamycin, radicicol, and chimeric inhibitors of the Hsp90 N-terminal ATP binding site. Curr Top Med Chem. 2006;6(11):1173-82. Review. PubMed PMID: 16842154.

4: Chiosis G, Caldas Lopes E, Solit D. Heat shock protein-90 inhibitors: a chronicle from geldanamycin to today's agents. Curr Opin Investig Drugs. 2006 Jun;7(6):534-41. Review. PubMed PMID: 16784024.

5: Neckers L. Chaperoning oncogenes: Hsp90 as a target of geldanamycin. Handb Exp Pharmacol. 2006;(172):259-77. Review. PubMed PMID: 16610363.

6: Miyata Y. Hsp90 inhibitor geldanamycin and its derivatives as novel cancer chemotherapeutic agents. Curr Pharm Des. 2005;11(9):1131-8. Review. PubMed PMID: 15853661.

7: Sausville EA. Geldanamycin analogs. J Chemother. 2004 Nov;16 Suppl 4:68-9. Review. PubMed PMID: 15688614.

8: Liao ZY, Zhen YS. [Advances in antitumor activity of the hsp90 inhibitor geldanamycin]. Yao Xue Xue Bao. 2001 Sep;36(9):716-20. Review. Chinese. PubMed PMID: 12580116.

9: Blagosklonny MV. Hsp-90-associated oncoproteins: multiple targets of geldanamycin and its analogs. Leukemia. 2002 Apr;16(4):455-62. Review. PubMed PMID: 11960322.

10: Ochel HJ, Eichhorn K, Gademann G. Geldanamycin: the prototype of a class of antitumor drugs targeting the heat shock protein 90 family of molecular chaperones. Cell Stress Chaperones. 2001 Apr;6(2):105-12. Review. Erratum in: Cell Stress Chaperones 2001 Jul;6(3):295. PubMed PMID: 11599571; PubMed Central PMCID: PMC434387.