Triazole substituted metal-free, metallo-phthalocyanines and their water soluble derivatives as potential cholinesterases inhibitors: Design, synthesis and in vitro inhibition study

被引：37

作者：

Arslan, Tayfun ^{[1
,2
]}

Cakir, Nezaket ^{[1
]}

Keles, Turgut ^{[3
]}

Yiklioglu, Zekeriya B. ^{[3
]}

Senturk, Murat ^{[4
]}

机构：

[1] Giresun Univ, Fac Sci, Dept Chem, TR-28200 Giresun, Turkey

[2] Giresun Univ, Tech Sci Vocat Sch, Dept Text, TR-28049 Giresun, Turkey

[3] Karadeniss Tech Univ, Fac Sci, Dept Chem, TR-61080 Trabzon, Turkey

[4] Ibrahim Cecen Univ Agri, Fac Pharm, Dept Basic Sci Pharm, TR-04100 Agri, Turkey

来源：

BIOORGANIC CHEMISTRY | 2019年 / 90卷

关键词：

Cholinesterases; Inhibitors; Water soluble phthalocyanine; ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; ACTIVATION;

D O I：

10.1016/j.bioorg.2019.103100

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In this study, 1,2,3-triazole substituted metal-free and metallo phthalocyanines (4, 5, 6) and their water soluble derivatives (4a, 5a, 6a) were designed, synthesized for the first time and tested in vitro on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Most phthalocyanines exhibited good inhibitory activities on these enzymes. Among the six phthalocyanines and starting compounds, 4a showed the most interesting profile as a submicromolar selective inhibitor of AChE (IC50 = 0.040 mu M) and 5a showed the most effective inhibitor of BChE (IC50 = 0.1198 mu M).

引用

页数：6

共 37 条

[1] Non-linear optothermal properties of metal-free phthalocyanine [J].

Abdeldayem, HA ;

Frazier, DO ;

Penn, BG ;

Smith, DD ;

Banks, CE .

THIN SOLID FILMS, 1999, 350 (1-2) :245-248

[2] The synthesis of axially disubstituted silicon phthalocyanines, their quaternized derivatives and first inhibitory effect on human cytosolic carbonic anhydrase isozymes hCA I and II [J].

Arslan, Tayfun ;

Biyiklioglu, Zekeriya ;

Senturk, Murat .

RSC ADVANCES, 2018, 8 (19) :10172-10178

[3] Synthesis of novel monostyryl and distyryl boron dipyrromethenes bearing 4-((2-hydroxyethyl)(methyl)amino group as cholinesterase and tyrosinase inhibitors [J].

Arslan, Tayfun ;

Keles, Turgut ;

Barut, Burak ;

Ozel, Arzu ;

Biyiklioglu, Zekeriya .

INORGANICA CHIMICA ACTA, 2018, 471 :121-125

[4]

Aucagne V., 2014, ANGEW CHEM INT EDIT, V51, P11320

[5]

Ballard Clive G., 2005, Current Alzheimer Research, V2, P307

[6] β-amyloid aggregation induced by human acetylcholinesterase:: inhibition studies [J].

Bartolini, M ;

Bertucci, C ;

Cavrini, V ;

Andrisano, V .

BIOCHEMICAL PHARMACOLOGY, 2003, 65 (03) :407-416

[7] Synthesis, DNA interaction, topoisomerase I, II inhibitory and cytotoxic effects of water soluble silicon (IV) phthalocyanine and napthalocyanines bearing 1-acetylpiperazine units [J].

Bas, Huseyin ;

Barut, Burak ;

Biyiklioglu, Zekeriya ;

Ozel, Arzu .

DYES AND PIGMENTS, 2019, 160 :136-144

[8] Substituted phthalocyanines and their electropolymerization properties [J].

Bayrak, Riza ;

Akcay, Hakki Turker ;

Biyiklioglu, Zekeriya ;

Degirmencioglu, Ismail .

SYNTHETIC METALS, 2016, 220 :643-652

[9] Synthesis and spectroscopic properties of a series of octacationic water-soluble phthalocyanines [J].

Biyiklioglu, Zekeriya ;

Kantekin, Halit .

SYNTHETIC METALS, 2011, 161 (11-12) :943-948

[10] Synthesis, electrochemical, in-situ spectroelectrochemical and in-situ electrocolorimetric characterization of non-peripheral tetrasubstituted metal-free and metallophthalocyanines [J].

Biyiklioglu, Zekeriya ;

Cakir, Volkan ;

Koca, Atif ;

Kantekin, Halit .

DYES AND PIGMENTS, 2011, 89 (01) :49-55

← 1 2 3 4 →