Inhibitory Kinetics of a Trifluoromethyl-Containing 1,2,3-Triazole Derivative on Mushroom Tyrosinase Activity

被引:5
|
作者
Li Shu-Bai [1 ]
Nie Hua-Li [1 ]
Zhang Hai-Tao [1 ]
Xue Yong [1 ]
Chris Branford White [2 ]
Zhu Li-Min [1 ]
机构
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
[2] London Metropolitan Univ, Inst Hlth Res & Policy, London N7 8DB, England
基金
中国国家自然科学基金;
关键词
Trifluoromethyl-containing 1,2,3-triazole; Mushroom tyrosinase; Monophenolase; Diphenolase; Reversible parabolic-competitive inhibition; Copper chelation; MECHANISM; MONOPHENOL; FLAVONOLS; SUBSTRATE; ALCOHOLS; CATECHIN; ANALOGS; BINDING; ACIDS;
D O I
10.3866/PKU.WHXB20100115
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this study, we demonstrate that the trifluoromethyl-containing 1,2,3-triazole derivative (TF-TZ) inhibits mushroom tyrosinase. TF-TZ could inhibit the monophenolase and diphenolase activities and the inhibition is reversible. IC50 values of 30.4, and 34.5 mu mol.L-1 were estimated for the monophenolase activity and the diphenolase activity, respectively. TF-TZ could extend the lag period of the monophenolase activity. Kinetic analysis showed that parabolic-competitive inhibition of TF-TZ occurred on diphenolase. We proposed that two TF-TZ molecules combined with free tyrosinase to form enzyme-inhibitor complexes (El and EI2), and the inhibition constants (K-i1, for EI and K-i2 for EI2) were 76.9 and 9.71 mu mol.L-1, respectively. Moreover, the UV-Visible spectrum of a mixture of tyrosinase and TF-TZ exhibited a characteristic shoulder peak that could be assigned to chelation of TF-TZ to the active site.
引用
收藏
页码:215 / 220
页数:6
相关论文
共 50 条
  • [21] 8-Hydroxyquinoline 1,2,3-triazole derivatives with promising and selective antifungal activity
    da Silva, Naili Moreira
    Gentz, Caroline de Bem
    Reginatto, Paula
    Maciel Fernandes, Thais Helena
    Andrzejewski Kaminski, Tais Fernanda
    Lopes, William
    Quatrin, Priscilla M.
    Vainstein, Marilene Henning
    Abegg, Maxwel Adriano
    Lopes, Marcela Silva
    Fuentefria, Alexandre Meneghello
    de Andrade, Saulo Fernandes
    MEDICAL MYCOLOGY, 2021, 59 (05) : 431 - 440
  • [22] A 1,2,3-Triazole Derivative of Quinazoline Exhibits Antitumor Activity by Tethering RNF168 to SQSTM1/P62
    Wang, Fu-Cheng
    Peng, Bin
    Ren, Ting-Ting
    Liu, Shao-Peng
    Du, Jing-Rui
    Chen, Zi-Hao
    Zhang, Ting-Ting
    Gu, Xiaoyang
    Li, Mo
    Cao, Sheng-Li
    Xu, Xingzhi
    JOURNAL OF MEDICINAL CHEMISTRY, 2022, 65 (22) : 15028 - 15047
  • [23] Therapeutic potential of 1,2,3-triazole hybrids for leukemia treatment
    Yang, Wenchao
    Xuan, Bixia
    Li, Xiaofang
    Si, Haiyan
    Chen, Aiping
    ARCHIV DER PHARMAZIE, 2022, 355 (09)
  • [24] Regioselective Reduction of 1H-1,2,3-Triazole Diesters
    Butler, Christopher R.
    Bendesky, Justin
    Schoffstall, Allen Milton
    MOLECULES, 2021, 26 (18):
  • [25] Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity
    Vilanova, Concepcion
    Torijano-Gutierrez, Sandra
    Diaz-Oltra, Santiago
    Murga, Juan
    Falomir, Eva
    Carda, Miguel
    Alberto Marco, J.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 87 : 125 - 130
  • [26] Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives
    Ramirez-Villalva, Alejandra
    Gonzalez-Calderon, Davir
    Rojas-Garcia, Roxana I.
    Gonzalez-Romero, Carlos
    Tamariz-Mascarua, Joaquin
    Morales-Rodriguez, Macario
    Zavala-Segoviad, Nieves
    Fuentes-Benites, Aydee
    MEDCHEMCOMM, 2017, 8 (12) : 2258 - 2262
  • [27] Synthesis of Novel Isoindolo[ 2,1-a] quinazolinedione Derivatives Containing a 1,2,3-Triazole Ring System
    Esmaeili-Marandi, Fatemeh
    Saeedi, Mina
    Yavari, Issa
    Mahdavi, Mohammad
    Shafiee, Abbas
    HELVETICA CHIMICA ACTA, 2016, 99 (01) : 37 - 40
  • [28] Synthesis and biological evaluation of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties
    Mao, Mingzhen
    Li, Yuxin
    Liu, Qiaoxia
    Xiong, Lixia
    Zhang, Xiao
    Li, Zhengming
    JOURNAL OF PESTICIDE SCIENCE, 2015, 40 (3-4) : 138 - 142
  • [29] Synthesis, antioxidant and anti-tyrosinase activity of 1,2,4-triazole hydrazones as antibrowning agents
    Peng, Zhiyun
    Wang, Guangcheng
    Zeng, Qiao-Hui
    Li, Yufeng
    Wu, Yi
    Liu, Haiquan
    Wang, Jing Jing
    Zhao, Yong
    FOOD CHEMISTRY, 2021, 341
  • [30] Synthesis, Biological Activity, and Molecular Modeling Studies of 1H-1,2,3-Triazole Derivatives of Carbohydrates as α-Glucosidases Inhibitors
    Ferreira, Sabrina B.
    Sodero, Ana C. R.
    Cardoso, Mariana F. C.
    Lima, Emerson S.
    Kaiser, Carlos R.
    Silva, Floriano P., Jr.
    Ferreira, Vitor F.
    JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (06) : 2364 - 2375