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T9324

TAS-301

Name: TAS-301
Brand: SIGMA

≥95% (HPLC), solid

Synonym(s):

3-Bis-(4-methoxphenyl)methylene-2-indolinone

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₁₉NO₃

CAS Number:

193620-69-8

Molecular Weight:

357.40

MDL number:

MFCD05865245

UNSPSC Code:

12352202

PubChem Substance ID:

329826905

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assay

≥95% (HPLC)

form

solid

solubility

DMSO: 40 mg/mL

SMILES string

COc1ccc(cc1)\C(c2ccc(OC)cc2)=C3\C(=O)Nc4ccccc34

InChI

1S/C23H19NO3/c1-26-17-11-7-15(8-12-17)21(16-9-13-18(27-2)14-10-16)22-19-5-3-4-6-20(19)24-23(22)25/h3-14H,1-2H3,(H,24,25)

InChI key

KUEYYIJXBRWZIB-UHFFFAOYSA-N

Biochem/physiol Actions

Inhibitor of migration and proliferation in vascular smooth muscle cells; inhibitor of restenosis.

TAS-301 is known to block intimal thickening post balloon injury in rat carotid arteries[1]. It inhibits intimal thickening by blocking Ca2+/calmodulin-dependent protein kinase II (CaM kinase II) and cytoskeletal depolymerization[2]. Moreover, TAS 301 can also inhibit receptor-regulated influx of calcium in rat vascular smooth muscle cells (VSMCs)[3].

Preparation Note

TAS-301 is soluble in DMSO at 40 mg/ml.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

123K4604

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Tas-301, a new synthetic inhibitor of neointimal thickening after balloon injury, inhibits calcium-dependent signal transduction and cytoskeletal reorganization.

E Sasaki et al.

Pharmacology, 63(1), 17-27 (2001-06-16)

We previously demonstrated that a recently synthesized drug, TAS-301 [3-bis(4-methoxyphenyl)methylene-2-indolinone], inhibited neointimal thickening after single-balloon injury to the rat common carotid artery by inhibiting both the migration and proliferation processes of vascular smooth muscle cells (VSMCs). The purpose of this

TAS-301 blocks receptor-operated calcium influx and inhibits rat vascular smooth muscle cell proliferation induced by basic fibroblast growth factor and platelet-derived growth factor.

E Sasaki et al.

Japanese journal of pharmacology, 84(3), 252-258 (2001-01-04)

The purpose of this study was to determine the effect of a recently synthesized drug, TAS-301 [3-bis(4-methoxyphenyl)methylene-2-indolinone], on vascular smooth muscle cell (VSMC) proliferation and the intracellular signal transduction pathways involved in VSMC proliferation. In an in vitro assay, TAS-301

TAS-301, an inhibitor of smooth muscle cell migration and proliferation, inhibits intimal thickening after balloon injury to rat carotid arteries.

Y Muranaka et al.

The Journal of pharmacology and experimental therapeutics, 285(3), 1280-1286 (1998-06-17)

The purpose of this study was to determine the efficacy and the possible mechanism of action of a recently synthesized drug, TAS-301 [3-bis (4-methoxyphenyl)methylene-2-indolinone], on intimal formation in comparison with those of tranilast, the clinical efficacy of which was reported

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