Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis

P. Thanigaimalai; Ki Cheul Lee; Seong Cheol Bang; Jee Hyun Lee; Cheong Yong Yun; Eunmiri Roh; Bang Yeon Hwang; Youngsoo Kim; Sang Hun Jung

doi:10.1016/j.bmc.2009.12.044

Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis

P. Thanigaimalai, Ki Cheul Lee, Seong Cheol Bang, Jee Hyun Lee, Cheong Yong Yun, Eunmiri Roh, Bang Yeon Hwang, Youngsoo Kim, Sang Hun Jung

The Hormel Institute

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

32 Scopus citations

Abstract

The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of α-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (>100% inhibition at 10 μM, IC₅₀ = 1.2 μM) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (>100% inhibition at 10 μM, IC₅₀ = 0.76 μM) exhibited potent inhibitory effect against α-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.

Original language	English (US)
Pages (from-to)	1135-1142
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	3
DOIs	https://doi.org/10.1016/j.bmc.2009.12.044
State	Published - Feb 1 2010

Bibliographical note

Funding Information:
This research was financially supported by a grant ( R01-2007-000-20099-0 ) from the National Research Foundation of Korea .

Keywords

Hypopimenting
Melanogenesis
Tetrahydropyrimidine-2(1H)-thione
α-MSH-induced melanin production

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10.1016/j.bmc.2009.12.044

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title = "Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis",

abstract = "The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of α-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (>100% inhibition at 10 μM, IC50 = 1.2 μM) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (>100% inhibition at 10 μM, IC50 = 0.76 μM) exhibited potent inhibitory effect against α-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.",

keywords = "Hypopimenting, Melanogenesis, Tetrahydropyrimidine-2(1H)-thione, α-MSH-induced melanin production",

author = "P. Thanigaimalai and Lee, {Ki Cheul} and Bang, {Seong Cheol} and Lee, {Jee Hyun} and Yun, {Cheong Yong} and Eunmiri Roh and Hwang, {Bang Yeon} and Youngsoo Kim and Jung, {Sang Hun}",

note = "Funding Information: This research was financially supported by a grant ( R01-2007-000-20099-0 ) from the National Research Foundation of Korea .",

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doi = "10.1016/j.bmc.2009.12.044",

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AU - Thanigaimalai, P.

AU - Lee, Ki Cheul

AU - Bang, Seong Cheol

AU - Lee, Jee Hyun

AU - Yun, Cheong Yong

AU - Roh, Eunmiri

AU - Hwang, Bang Yeon

AU - Kim, Youngsoo

AU - Jung, Sang Hun

N1 - Funding Information: This research was financially supported by a grant ( R01-2007-000-20099-0 ) from the National Research Foundation of Korea .

PY - 2010/2/1

Y1 - 2010/2/1

N2 - The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of α-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (>100% inhibition at 10 μM, IC50 = 1.2 μM) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (>100% inhibition at 10 μM, IC50 = 0.76 μM) exhibited potent inhibitory effect against α-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.

AB - The series of imidazoldine-2-thiones 2 and tetrahydropyrimidine-2-thiones 3 were discovered as inhibitor of α-MSH-induced melanin production in melanoma B16 cells. The primary bioassay showed that 1-(4-ethylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3e (>100% inhibition at 10 μM, IC50 = 1.2 μM) and 1-(4-tert-butylbenzyl)-tetrahydropyrimidine-2(1H)-thione 3f (>100% inhibition at 10 μM, IC50 = 0.76 μM) exhibited potent inhibitory effect against α-MSH-induced melanin production. Compounds 3 inhibit the biosynthesis of tyrosinase without affecting its catalytic activity in melanogenesis.

KW - Hypopimenting

KW - Melanogenesis

KW - Tetrahydropyrimidine-2(1H)-thione

KW - α-MSH-induced melanin production

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Inhibitory effect of novel tetrahydropyrimidine-2(1H)-thiones on melanogenesis

Abstract

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