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S-methyl-KE-298

Names

[ CAS No. ]:
143584-75-2

[ Name ]:
S-methyl-KE-298

[Synonym ]:
Benzenebutanoic acid, 4-methyl-α-[(methylthio)methyl]-γ-oxo-
4-(4-Methylphenyl)-2-[(methylsulfanyl)methyl]-4-oxobutanoic acid
4-(4-methylphenyl)-2-methylthiomethyl-4-oxobutanoic acid

Biological Activity

[Description]:

S-methyl-KE-298 is an active metabolite of KE-298. KE-298 inhibits matrix metalloproteinase (MMP-1) production from rheumatoid arthritis (RA) synovial cells.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[In Vitro]

S-methyl-KE-298 is a methyl conjugate of deacetyl-KE-298 is plasma[1]. In vitro protein binding of KE-298 and its plasma metabolites, deacetyl-KE-298 (M-1) and S-methyl-KE-298 (M-2), is high in rat (>97%), dog (>89%) and human plasma (>99%), respectively[2]. KE-298 blocks this IL-1β-induced pro-MMP-2 activation and MT1-MMP expression, but does not affect IL-1β-induced tissue inhibitor of metalloproteinase-2 (TIMP-2) secretion from rheumatoid synovial cells. KE-298 inhibits MMP-1 production from rheumatoid arthritis (RA) synovial cells by affecting a transcription factor, AP-1. KE-298 inhibits the basal levels of MT1-MMP expression of unstimulated rheumatoid synovial cells[3].

[References]

[1]. Yoshida H, et al. Identification of metabolites of KE-298, a new antirheumatic drug, and its physiological properties in rats. Biol Pharm Bull. 1996 Mar;19(3):424-9.

[2]. Endo H, et al. Stereoselectivity and species difference in plasma protein binding of KE-298 and its metabolites. Biol Pharm Bull. 2001 Jul;24(7):800-5.

[3]. Honda S, et al. Expression of membrane-type 1 matrix metalloproteinase in rheumatoid synovial cells. Clin Exp Immunol. 2001 Oct;126(1):131-6.


[Related Small Molecules]

GM 6001 | T-5224 | SB-3CT | Batimastat | Astragaloside IV | Marimastat (BB-2516) | edaravone | TAPI-2 | TAPI 1 | ISOGINKGETIN | Arctigenin | CTS-1027 | GI254023X | JNJ 0966 | CL-82198

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
457.2±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C13H16O3S

[ Molecular Weight ]:
252.329

[ Flash Point ]:
230.3±28.7 °C

[ Exact Mass ]:
252.082016

[ LogP ]:
2.84

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.565

[ Storage condition ]:
2-8℃

Related Compounds