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S3131

Sigma-Aldrich

Sulindac sulfide

≥98% (HPLC), solid

Synonym(s):

(Z)-5-Fluoro-2-methyl-1-[p-(methylthio)benzylidene]indene-3-acetic acid

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About This Item

Empirical Formula (Hill Notation):
C20H17FO2S
CAS Number:
32004-67-4
Molecular Weight:
340.41
EC Number:
250-892-2
MDL number:
MFCD00869764
UNSPSC Code:
12352200
PubChem Substance ID:
24899543
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

color

yellow

solubility

DMSO: ≥22 mg/mL

SMILES string

[H]\C(c1ccc(SC)cc1)=C2/C(C)=C(CC(O)=O)c3cc(F)ccc23

InChI

1S/C20H17FO2S/c1-12-17(9-13-3-6-15(24-2)7-4-13)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-

InChI key

LFWHFZJPXXOYNR-MFOYZWKCSA-N

Application

Human endothelial cells, HMEC-1 were treated with Sulindac sulfide and the effect on cell survival was studies by MTT assay.

Biochem/physiol Actions

Sulindac sulfide is a non-steroidal anti-inflammatory compound with a preference for COX-1; it is an inhibitor of Ras activation of Raf-1. It impairs nucleotide exchange on Ras by CDC25 and accelerates Ras hydrolysis of GTP by p120GAP. It is an active metabolite of sulindac. It is also shown to inhibit growth and induce apoptosis in human prostate cancer cells through a COX-1 and COX-2 independent mechanism. Sulindac sulfide is an analgesic that has antiproliferative and apoptotic effects. It inhibits the expression and activity of cyclooxygenase-2 in human colon cancer cells and reduces tumor burden in adenomatous polyposis patients.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Luise Richter et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(33), 14597-14602 (2010-08-04)
Following ectodomain shedding by beta-secretase, successive proteolytic cleavages within the transmembrane sequence (TMS) of the amyloid precursor protein (APP) catalyzed by gamma-secretase result in the release of amyloid-beta (Abeta) peptides of variable length. Abeta peptides with 42 amino acids appear
Z Zhang et al.
Gastroenterology, 118(6), 1012-1017 (2000-06-02)
Many reports indicate that nonsteroidal anti-inflammatory drugs (NSAIDs) have antineoplastic effects, but the precise molecular mechanism(s) responsible are unclear. We evaluated the effect of cyclooxygenase (COX) inhibitors (NSAIDs) on human colon carcinoma cells (HCA-7) and identified several genes that are
C Herrmann et al.
Oncogene, 17(14), 1769-1776 (1998-10-20)
The non-steroidal anti-inflammatory drug sulindac is used in cancer prevention and therapy, but the molecular aspects of its anti-tumor effect remain unresolved. In vivo the prodrug sulindac, is converted into the metabolite sulindac sulfide. We found that sulindac sulfide strongly
J T Lim et al.
Biochemical pharmacology, 58(7), 1097-1107 (1999-09-14)
We examined the activity of two metabolites of sulindac (a nonsteroidal anti-inflammatory drug), sulindac sulfide and sulindac sulfone (exisulind, Prevatec), and a novel highly potent analog of exisulind (CP248) on a series of human prostate epithelial cell lines. Marked growth
Tomas Borgegard et al.
The Journal of biological chemistry, 287(15), 11810-11819 (2012-02-16)
γ-Secretase-mediated cleavage of amyloid precursor protein (APP) results in the production of Alzheimer disease-related amyloid-β (Aβ) peptides. The Aβ42 peptide in particular plays a pivotal role in Alzheimer disease pathogenesis and represents a major drug target. Several γ-secretase modulators (GSMs)
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