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SML1278

Sigma-Aldrich

Geldanamycin Ready Made Solution

1 mg/mL, from Streptomyces hygroscopicus

Synonym(s):

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)

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About This Item

Empirical Formula (Hill Notation):
C29H40N2O9
CAS Number:
30562-34-6
Molecular Weight:
560.64
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Streptomyces hygroscopicus

Quality Level

200

form

DMSO solution

storage condition

protect from light

concentration

1 mg/mL

antibiotic activity spectrum

neoplastics

Mode of action

enzyme | inhibits

shipped in

dry ice

storage temp.

−20°C

SMILES string

N1C2=CC(=O)C(=C(C[C@H](C[C@@H]([C@@H]([C@H](\C=C(\[C@@H]([C@H](\C=C/C=C(/C1=O)\C)OC)OC(=O)N)/C)C)O)OC)C)C2=O)OC

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

General description

Chemical structure: benzenoid

Application

Geldanamycin Ready-Made Solution has been used as a heat shock protein 90 (Hsp90) inhibitor to pre-treat proteosome holo-enzyme during proteasome assay to study the role of proteasome on fibril fragmentation.

Biochem/physiol Actions

Geldanamycin is a benzoquinone ansamycin and is a well known tyrosine kinase inhibitor. It possesses anticancer effects and shows therapeutic effects against osteosarcoma.
Geldanamycin is a potent antitumor antibiotic active at nanomolar concentration against 60 cell lines. Geldanamycin 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, Geldanamycin is a potent inhibitor of the nuclear hormone receptor family.

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

188.6 °F

Flash Point(C)

87 °C

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

SML1278-1ML-PW:
SML1278-VAR:
SML1278-1ML:
SML1278-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000305639
0000310345
0000174303
11180206

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Rachel Cliffe et al.
Cell reports, 26(8), 2140-2149 (2019-02-21)
Filamentous aggregates (fibrils) are regarded as the final stage in the assembly of amyloidogenic proteins and are formed in many neurodegenerative diseases. Accumulation of aggregates occurs as a result of an imbalance between their formation and removal. Here we use
Magdalena Gorska et al.
PloS one, 8(8), e71135-e71135 (2013-09-10)
Osteosarcoma is one of the most malignant tumors of childhood and adolescence that is often resistant to standard chemo- and radio-therapy. Geldanamycin and geldanamycin analogs have been recently studied as potential anticancer agents for osteosarcoma treatment. Here, for the first

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