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Key Documents

SML0896

Sigma-Aldrich

MCC-555

≥98% (HPLC)

Synonym(s):

5-[[6-[(2-Fluorophenyl)methoxy]-2-naphthalenyl]methyl]-2,4-thiazolidinedione, Isaglitazone, Netoglitazone, RWJ 241947

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About This Item

Empirical Formula (Hill Notation):
C21H16FNO3S
CAS Number:
161600-01-7
Molecular Weight:
381.42
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25)

InChI key

PKWDZWYVIHVNKS-UHFFFAOYSA-N

Biochem/physiol Actions

MCC-555 is a thiazolidinedione class anti-diabetic compound. In rodent models, MCC-555 attenuates the development of diabetes, maintains B-cell function and improves insulin sensitivity. The compound MCC-555 also inhibits proliferation of several cancer cell lines and reduces tumor growth in xenograft models.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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S Ulrich et al.
Experimental cell research, 310(1), 196-204 (2005-08-23)
Histone deacetylase-inhibitors affect growth and differentiation of intestinal epithelial cells by inducing expression of several transcription factors, e.g. Peroxisome proliferator-activated receptor gamma (PPARgamma) or vitamin D receptor (VDR). While activation of VDR by butyrate mainly seems to be responsible for
L Pickavance et al.
British journal of pharmacology, 125(4), 767-770 (1998-12-01)
1. Young (6-week-old) pre-diabetic Zucker Diabetic Fatty (ZDF) rats displaying impaired glucose tolerance (IGT), moderate hyperglycaemia and hyperinsulinaemia were treated with the novel thiazolidinedione, MCC-555, for 28 days, during which time beta-cell failure and progression to overt diabetes occurs. 2.
Kyung-Won Min et al.
Toxicology and applied pharmacology, 263(2), 225-232 (2012-07-04)
MCC-555 is a novel PPARα/γ dual ligand of the thiazolidinedione class and was recently developed as an anti-diabetic drug with unique properties. MCC-555 also has anti-proliferative activity through growth inhibition and apoptosis induction in several cancer cell types. Our group
Kiyoshi Yamaguchi et al.
Molecular cancer therapeutics, 5(5), 1352-1361 (2006-05-30)
Apoptosis and/or differentiation induction caused by the peroxisome proliferator-activated receptor gamma (PPARgamma) ligand is a promising approach to cancer therapy. The thiazolidinedione derivative MCC-555 has an apoptotic activity in human colorectal cancer cells, accompanied by up-regulation of a proapoptotic nonsteroidal
M J Reginato et al.
The Journal of biological chemistry, 273(49), 32679-32684 (1998-11-26)
Thiazolidinediones (TZDs) constitute an exciting new class of antidiabetic compounds, which function as activating ligands for peroxisome proliferator-activated receptor gamma (PPARgamma). Until now, there has been an excellent correlation between in vivo hypoglycemic potency and in vitro binding and activation
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