(E)-(1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline: Synthesis, Characterization, DNA-Interaction, and Evaluation of Activity Against Drug-Resistant Cell Lines

被引：13
|
作者：
Matiadis, Dimitris [1 ]
Mavroidi, Barbara [1 ]
Panagiotopoulou, Angeliki [1 ]
Methenitis, Constantinos [2 ]
Pelecanou, Maria [1 ]
Sagnou, Marina [1 ]
机构：
[1] Natl Ctr Sci Res Demokritos, Inst Biosci & Applicat, Athens 15310, Greece
[2] Natl & Kapodistrian Univ Athens, Dept Chem, Athens 15784, Greece
来源：
MOLBANK | 2020年 / 2020卷 / 01期
关键词：
pyrazolines; curcuminoids; nitrogen heterocycles; cytotoxic; DNA binding; MDR reversal; 1,3,5-TRISUBSTITUTED PYRAZOLINES; ANTIINFLAMMATORY ACTIVITY; CURCUMIN; ANALOGS; BINDING; ANTIMALARIAL; DERIVATIVES; ANTITUMOR; MOIETIES;
D O I：
10.3390/M1114
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
(E)-1-(4-Ethoxycarbonylphenyl)-5-(3,4-dimethoxyphenyl)-3-(3,4-dimethoxystyryl)-2-pyrazoline was synthesized via the cyclization reaction between the monocarbonyl curcuminoid (2E,6E)-2,6-bis(3,4-dimethoxybenzylidene)acetone and ethyl hydrazinobenzoate in high yield and purity (>95% by High-performance liquid chromatography (HPLC)). The compound has been fully characterized by H-1, C-13 NMR, FTIR, UV-Vis and HRMS and its activity was evaluated in terms of its potential interaction with DNA as well as its cytotoxicity against resistant and non-resistant tumor cells. Both DNA thermal denaturation and DNA viscosity measurements revealed that a significant intercalation binding takes place upon treatment of the DNA with the synthesized pyrazoline, causing an increase in melting temperature by 3.53 +/- 0.11 degrees C and considerable DNA lengthening and viscosity increase. However, neither re-sensitisation of Doxorubicin (DO X)-resistant breast cancer and multidrug resistance (MDR) reversal nor synergistic activity with DOX by potentially increasing the DOX cell killing ability was observed.
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页数：10
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