Competitive inhibition of mushroom tyrosinase by 4-substituted benzaldehydes

被引:141
作者
Jiménez, M [1 ]
Chazarra, S [1 ]
Escribano, J [1 ]
Cabanes, J [1 ]
García-Carmona, F [1 ]
机构
[1] Univ Murcia, Dept Bioquim & Biol Mol A, Unidad Docente Biol, E-30080 Murcia, Spain
关键词
tyrosinase; monophenolase; diphenolase; cuminaldehyde; competitive inhibitors;
D O I
10.1021/jf010194h
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
A kinetic study of the inhibition of mushroom tyrosinase by 4-substituted benzaldehydes showed that these compounds behave as classical competitive inhibitors, inhibiting the oxidation Of L-3,4-dihydroxyphenylalanine (L-DOPA) by mushroom tyrosinase (o-diphenolase activity). The kinetic parameter (K-I) characterizing this inhibition was evaluated for all of the seven compounds assayed. Cuminaldehyde showed the most potent inhibitory activity (K-I = 9 muM). It also inhibited the oxidation of L-tyrosine by mushroom tyrosinase (o-monophenolase activity) in a competitive manner. The corresponding kinetic parameter for this inhibition was evaluated (K-I = 0.12 mM).
引用
收藏
页码:4060 / 4063
页数:4
相关论文
共 50 条
[41]   Novel hydroxypyridinone derivatives containing an oxime ether moiety: Synthesis, inhibition on mushroom tyrosinase and application in anti-browning of fresh-cut apples [J].
Shao, Le-Le ;
Wang, Xiao-Ling ;
Chen, Kai ;
Dong, Xiao-Wu ;
Kong, Li-Min ;
Zhao, De-Yin ;
Hider, Robert C. ;
Zhou, Tao .
FOOD CHEMISTRY, 2018, 242 :174-181
[42]   Design, synthesis, spectroscopic characterization, in vitro tyrosinase inhibition, antioxidant evaluation, in silico and kinetic studies of substituted indole-carbohydrazides [J].
Iraji, Aida ;
Sheikhi, Negar ;
Attarroshan, Mahshid ;
Ardani, Gholam Reaz Sharifi ;
Kabiri, Maryam ;
Bafghi, Ali Naghibi ;
Kobarfard, Farzad ;
Rezaei, Zahra ;
Khoshneviszadeh, Mehdi ;
Foroumadi, Alireza ;
Mirfazli, Seyedeh Sara .
BIOORGANIC CHEMISTRY, 2022, 129
[43]   Antimelanogenic effect of 4-hydroxylonchocarpin through the inhibition of tyrosinase-related proteins and MAPK phosphatase [J].
Lim, Jihyun ;
Nam, Sorim ;
Li, Hua ;
Yang, Young ;
Lee, Myeong-Sok ;
Lee, Hee Gu ;
Ryu, Jae-Ha ;
Lim, Jong-Seok .
EXPERIMENTAL DERMATOLOGY, 2016, 25 (07) :574-576
[44]   Identification of novel C-2 symmetric Bis-Azo-Azamethine molecules as competitive inhibitors of mushroom tyrosinase and free radical scavengers: synthesis, kinetics, and molecular docking studies [J].
Saeed, Aamer ;
Ahmed, Atteeque ;
Ali Channar, Pervaiz ;
Shabir, Ghulam ;
Hassan, Abbas ;
Zia-ur-Rehman ;
Abbas, Qamar ;
Hassan, Mubashir ;
Raza, Hussain ;
Seo, Sung-Yum ;
El-Seedi, Hesham R. .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2022, 40 (10) :4419-4428
[45]   Thiazol-4(5H)-one analogs as potent tyrosinase inhibitors: Synthesis, tyrosinase inhibition, antimelanogenic effect, antioxidant activity, and in silico docking simulation [J].
Park, Yu Jung ;
Jung, Hee Jin ;
Kim, Hye Jin ;
Park, Hye Soo ;
Lee, Jieun ;
Yoon, Dahye ;
Kang, Min Kyung ;
Kim, Ga Young ;
Ullah, Sultan ;
Kang, Dongwan ;
Park, Yujin ;
Chun, Pusoon ;
Chung, Hae Young ;
Moon, Hyung Ryong .
BIOORGANIC & MEDICINAL CHEMISTRY, 2024, 98
[46]   Investigation of tyrosinase inhibition by some 1,2,4 triazole derivative compounds: in vitro and in silico mechanisms [J].
Demir, Elif Ayazoglu ;
Colak, Ahmet ;
Kalfa, Aylin ;
Yasar, Ahmet ;
Bekircan, Olcay ;
Akatin, Melike Yildirim .
TURKISH JOURNAL OF BIOCHEMISTRY-TURK BIYOKIMYA DERGISI, 2019, 44 (04) :473-481
[47]   Inhibition of α/β-K6P2W18O62•10H2O on the Activity of Mushroom Tyrosinase and Its Antimicrobial Effects [J].
Hu Xi-yu ;
Chen Bing-nian ;
Wang Li ;
Chen Fa-he .
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2012, 28 (05) :862-865
[48]   A novel synthetic compound, (Z)-5-(3-hydroxy-4-methoxybenzylidene)-2-iminothiazolidin-4-one (MHY773) inhibits mushroom tyrosinase [J].
Jung, Hee Jin ;
Lee, Min Jung ;
Park, Yeo Jin ;
Noh, Sang Gyun ;
Lee, A. Kyoung ;
Moon, Kyoung Mi ;
Lee, Eun Kyeong ;
Bang, Eun Jin ;
Park, Yun Jung ;
Kim, Su Jeong ;
Yang, Jungho ;
Ullah, Sultan ;
Chun, Pusoon ;
Jung, Young Suk ;
Moon, Hyung Ryong ;
Chung, Hae Young .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2018, 82 (05) :759-767
[49]   Melanin Biosynthesis Inhibitors from Wood of Artocarpus heterophyllus: The Effect of Isoprenoid Substituent of Flavone with 4-Substituted Resorcinol Moiety at B Ring [J].
Arung, Enos T. ;
Shimizu, Kuniyoshi ;
Tanaka, Hiroyuki ;
Kondo, Ryuichiro .
LETTERS IN DRUG DESIGN & DISCOVERY, 2010, 7 (08) :602-605
[50]   Synthesis, Kinetics and Computational Explorations of 4-Phenylpiperazine Bearing N-(Aryl)-3-substituted-benzamides as Auspicious Tyrosinase Inhibitors [J].
Zeb, Aurang ;
Abbasi, Muhammad Athar ;
Aziz-ur-Rehman ;
Siddiqui, Sabahat Zahra ;
Hassan, Mubashir ;
Javed, Qamar ;
Rafiq, Muhammad ;
Ali, Anser ;
Shah, Syed Adnan Ali ;
Kloczkowski, Andrzej .
CHEMISTRY & BIODIVERSITY, 2024, 21 (04)