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SML0985

Sigma-Aldrich

Geldanamycin-Biotin

≥98% (HPLC)

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Synonym(s):
4,7,10,13-Tetraoxa-16-azaheneicosanamide, Biotinyl-geldanamycin, Biotinylated-Geldanamycin, N-[2-[2-[2-[[(8S,9S,12S,13R,14S,16R)-9-[(aminocarbonyl)oxy]-13-hydroxy-8,14-dimethoxy-4,12,16-trimethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaen-19-yl]amino]ethoxy]ethoxy]ethyl]-21-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-17-oxo-
Empirical Formula (Hill Notation):
C55H87N7O17S
CAS Number:
Molecular Weight:
1150.38
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

DMSO: soluble 10 mg/mL
methanol: soluble 3 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

O=C(C(NCCOCCOCCNC(CCOCCOCCOCCOCCNC(CCCC[C@@H]1SC[C@]([C@]1([H])N2)([H])NC2=O)=O)=O)=C3C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C/[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(C)\C4=O)C=C(N4)C3=O

InChI

1S/C54H85N7O17S/c1-35-31-38-48(41(62)33-39(51(38)66)59-52(67)37(3)9-8-10-42(70-4)43(78-53(55)68)14-13-36(2)50(65)44(32-35)71-5)58-18-22-75-25-24-73-21-17-57-47(64)15-19-72-23-27-76-29-30-77-28-26-74-20-16-56-46(63)12-7-6-11-45-49-40(34-79-45)60-54(69)61-49/h8-10,13-14,33,35-36,40,42-45,49-50,58,65H,6-7,11-12,15-32,34H2,1-5H3,(H2,55,68)(H,56,63)(H,57,64)(H,59,67)(H2,60,61,69)/b10-8-,14-13+,37-9+/t35-,36+,40+,42+,43+,44+,45+,49+,50-/m1/s1

InChI key

FCOFNJAJLZRONU-IULOFKFCSA-N

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This Item
SML1278A8476762024
Geldanamycin-Biotin ≥98% (HPLC)

SML0985

Geldanamycin-Biotin

Geldanamycin Ready Made Solution 1 mg/mL, from Streptomyces hygroscopicus

SML1278

Geldanamycin Ready Made Solution

Azide-PEG3-biotin conjugate

762024

Azide-PEG3-biotin conjugate

assay

≥98% (HPLC)

assay

-

assay

≥98% (HPLC)

assay

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO: soluble 10 mg/mL, H2O: insoluble, methanol: soluble 3 mg/mL

solubility

-

solubility

DMSO: soluble, methanol: soluble

solubility

-

storage condition

desiccated, protect from light

storage condition

protect from light

storage condition

-

storage condition

-

Biochem/physiol Actions

Geldanamycin-Biotin is a benzoquinone ansamycin antitumor antibiotic. Geldanamycin binds specifically to Hsp90 (HeatShock 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 stess response.
Geldanamycin-Biotin is a cell permeable HSP90 inhibitor.
Geldanamycin was isolated from Streptomyces hygroscopicus in 1970 and is highly hepatotoxic. It helps to decrease the acute respiratory distress syndrome and induces the survival of mice affected with virulent H5N1 influenza virus. Geldanamycin also blocks the chaperone actions of the Hsp90 protein.

Other Notes

It is recommended that the product be stored desiccated and protected form light at at −20 °C. Geldanamycin-Biotin as supplied is stable for 5 years when stored properly. Solutions is DMSO are stable for at least two weeks when stored at −20 °C. Geldanamycin decomposes in acidic solution.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Geldanamycin Reduces Acute Respiratory Distress Syndrome and Promotes the Survival of Mice Infected with the Highly Virulent H5N1 Influenza Virus.
Wang V, et al.
Frontiers in Cellular and Infection Microbiology, 7, 267-267 (2017)
Anti-malarial activity of geldanamycin derivatives in mice infected with Plasmodium yoelii
Mout R, et al.
Malaria Journal, 11(1), 54-54 (2012)
Romel Rosales Ramirez et al.
Journal of virology, 93(4) (2018-11-23)
Dengue virus (DENV) is a mosquito-borne virus of the family Flaviviridae The RNA viral genome encodes three structural and seven nonstructural proteins. Nonstructural protein 1 (NS1) is a multifunctional protein actively secreted in vertebrate and mosquito cells during infection. In

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