Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells

Melanin is a form of pigment that gives colour to human skin, hair and eyes. Whilst it protects against skin damage from the sun, accumulation of excessive amounts of epidermal melanin can lead to various dermatological disorders. This study aimed to evaluate the effects of three selected oxadiazo...

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Main Authors:	Mohd Aluwi, Mohd Fadhlizil Fasihi, Rullah, Kamal, Tan, Huan Huan, Chan, Kok Meng, Tan, Si Jie, Leong, Sze Wei, Mansor, Ahmad Hasnan, Yamin, Bohari M., Lam, Kok Wai
Format:	Article
Language:	English
Published:	Royal Society of Chemistry 2016
Subjects:	RS403 Materia Medica-Pharmaceutical Chemistry
Online Access:	http://irep.iium.edu.my/73761/ http://irep.iium.edu.my/73761/ http://irep.iium.edu.my/73761/1/Kamal%20Rullah%2010.pdf

id	iium-73761
recordtype	eprints
spelling	iium-737612019-09-17T08:17:09Z http://irep.iium.edu.my/73761/ Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Tan, Huan Huan Chan, Kok Meng Tan, Si Jie Leong, Sze Wei Mansor, Ahmad Hasnan Yamin, Bohari M. Lam, Kok Wai RS403 Materia Medica-Pharmaceutical Chemistry Melanin is a form of pigment that gives colour to human skin, hair and eyes. Whilst it protects against skin damage from the sun, accumulation of excessive amounts of epidermal melanin can lead to various dermatological disorders. This study aimed to evaluate the effects of three selected oxadiazoles on the o-diphenolase mushroom tyrosinase activity and their cytotoxic effects on SK-MEL-28 malignant melanoma cells. The results showed that compounds 1, 2 and 3 exhibited significant inhibition on the diphenolase activity of mushroom tyrosinase with IC50 values of 40.46 mM, 27.42 mM and 32.51 mM, respectively. Further kinetic studies revealed that compounds 1 (Ki ¼ 3.8 mM) and 3 (Ki ¼ 3.9 mM) exhibited a mixed-type inhibition while compound 2 (Ki ¼ 0.7 mM) displayed a competitive-type inhibition as suggested by the Lineweaver–Burk plots. Molecular docking and dynamics simulations were also performed to understand the binding behaviour of compound 2 in the active site of tyrosinase. Finally, all three compounds displayed relatively low cytotoxicity to SK-MEL-28 cells up to 100 mM treatment via MTT assay. Royal Society of Chemistry 2016 Article PeerReviewed application/pdf en http://irep.iium.edu.my/73761/1/Kamal%20Rullah%2010.pdf Mohd Aluwi, Mohd Fadhlizil Fasihi and Rullah, Kamal and Tan, Huan Huan and Chan, Kok Meng and Tan, Si Jie and Leong, Sze Wei and Mansor, Ahmad Hasnan and Yamin, Bohari M. and Lam, Kok Wai (2016) Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells. RSC Advances, 6 (76). pp. 72177-72184. ISSN 2046-2069 https://pubs.rsc.org/en/content/articlelanding/2016/ra/c6ra12754a#!divAbstract
repository_type	Digital Repository
institution_category	Local University
institution	International Islamic University Malaysia
building	IIUM Repository
collection	Online Access
language	English
topic	RS403 Materia Medica-Pharmaceutical Chemistry
spellingShingle	RS403 Materia Medica-Pharmaceutical Chemistry Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Tan, Huan Huan Chan, Kok Meng Tan, Si Jie Leong, Sze Wei Mansor, Ahmad Hasnan Yamin, Bohari M. Lam, Kok Wai Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells
description	Melanin is a form of pigment that gives colour to human skin, hair and eyes. Whilst it protects against skin damage from the sun, accumulation of excessive amounts of epidermal melanin can lead to various dermatological disorders. This study aimed to evaluate the effects of three selected oxadiazoles on the o-diphenolase mushroom tyrosinase activity and their cytotoxic effects on SK-MEL-28 malignant melanoma cells. The results showed that compounds 1, 2 and 3 exhibited significant inhibition on the diphenolase activity of mushroom tyrosinase with IC50 values of 40.46 mM, 27.42 mM and 32.51 mM, respectively. Further kinetic studies revealed that compounds 1 (Ki ¼ 3.8 mM) and 3 (Ki ¼ 3.9 mM) exhibited a mixed-type inhibition while compound 2 (Ki ¼ 0.7 mM) displayed a competitive-type inhibition as suggested by the Lineweaver–Burk plots. Molecular docking and dynamics simulations were also performed to understand the binding behaviour of compound 2 in the active site of tyrosinase. Finally, all three compounds displayed relatively low cytotoxicity to SK-MEL-28 cells up to 100 mM treatment via MTT assay.
format	Article
author	Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Tan, Huan Huan Chan, Kok Meng Tan, Si Jie Leong, Sze Wei Mansor, Ahmad Hasnan Yamin, Bohari M. Lam, Kok Wai
author_facet	Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Tan, Huan Huan Chan, Kok Meng Tan, Si Jie Leong, Sze Wei Mansor, Ahmad Hasnan Yamin, Bohari M. Lam, Kok Wai
author_sort	Mohd Aluwi, Mohd Fadhlizil Fasihi
title	Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells
title_short	Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells
title_full	Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells
title_fullStr	Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells
title_full_unstemmed	Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells
title_sort	synthesis and effects of oxadiazole derivatives on tyrosinase activity and human sk-mel-28 malignant melanoma cells
publisher	Royal Society of Chemistry
publishDate	2016
url	http://irep.iium.edu.my/73761/ http://irep.iium.edu.my/73761/ http://irep.iium.edu.my/73761/1/Kamal%20Rullah%2010.pdf
first_indexed	2023-09-18T21:44:35Z
last_indexed	2023-09-18T21:44:35Z
_version_	1777413364403666944

Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells

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