Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

Ho Sik Rho; Soo Mi Ahn; Dae Sung Yoo; Myung Kyoo Kim; Dong Ha Cho; Jae Youl Cho

doi:10.1016/j.bmcl.2010.09.042

Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

Ho Sik Rho, Soo Mi Ahn, Dae Sung Yoo, Myung Kyoo Kim, Dong Ha Cho, Jae Youl Cho

Research output: Contribution to journal › Article › peer-review

79 Scopus citations

Abstract

This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities.

Original language	English
Pages (from-to)	6569-6571
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1016/j.bmcl.2010.09.042
State	Published - 15 Nov 2010
Externally published	Yes

Keywords

Anti-inflammatory property
Derivatives
Kojyl thioether
Tyrosinase

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10.1016/j.bmcl.2010.09.042

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title = "Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties",

abstract = "This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities.",

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doi = "10.1016/j.bmcl.2010.09.042",

language = "English",

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T1 - Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

AU - Rho, Ho Sik

AU - Ahn, Soo Mi

AU - Yoo, Dae Sung

AU - Kim, Myung Kyoo

AU - Cho, Dong Ha

AU - Cho, Jae Youl

PY - 2010/11/15

Y1 - 2010/11/15

N2 - This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities.

AB - This study was conducted to examine the tyrosinase inhibitory and anti-inflammatory activities of kojic acid derivatives. A series of kojic acid derivatives containing thioether, sulfoxide, and sulfone linkages were synthesized. In the tyrosinase assay, kojyl thioether derivatives containing appropriate lipophilic alkyl chains (pentane, hexane, and cyclohexane) showed potent inhibitory activity. However, sulfoxides and sulfones exhibited decreased activity. Similar experimental results were obtained with inhibitory activities of NO production being induced by LPS. The presence of thioether linkage and appropriated lipophilic acid moiety was critical for the tyrosinase inhibitory and anti-inflammatory activities.

KW - Anti-inflammatory property

KW - Derivatives

KW - Kojyl thioether

KW - Tyrosinase

UR - https://www.scopus.com/pages/publications/77958049068

U2 - 10.1016/j.bmcl.2010.09.042

DO - 10.1016/j.bmcl.2010.09.042

M3 - Article

C2 - 20934336

AN - SCOPUS:77958049068

SN - 0960-894X

VL - 20

SP - 6569

EP - 6571

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 22

ER -

Kojyl thioether derivatives having both tyrosinase inhibitory and anti-inflammatory properties

Abstract

Keywords

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