Antiproliferative activities of 2-hydroxyethyl substituted benzimidazolium salts and their palladium complexes against human cancerous cell lines

被引:43
|
作者
Akkoc, Senem [1 ]
机构
[1] Suleyman Demirel Univ, Fac Pharm, Dept Basic Pharmaceut Sci, TR-32260 Isparta, Turkey
关键词
Anticancer; benzimidazolium salts; cytotoxic activity; N-heterocyclic carbene; PEPPSI; N-HETEROCYCLIC CARBENE; CYTOTOXIC ACTIVITY; CATALYTIC-ACTIVITY; PEPPSI COMPLEXES; CRYSTAL-STRUCTURE; IN-VITRO; DERIVATIVES; LIGANDS; DESIGN;
D O I
10.1080/00397911.2019.1650187
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzimidazolium salts (1a and 1b) and respective palladium complexes (2a and 2b) were prepared and characterized with H-1 and C-13 NMR, IR, elemental analysis as well as HRMS (for 2a). All target compounds were screened as potential anticancer agents against human cell lines for assessing their cytotoxicity. Heterocyclic organic compounds (1a and 1b) showed more cytotoxic activity than their complexes (2a and 2b) in the tested two cell lines. Particularly, a benzimidazolium salt including a 4-methylbenzyl group had a high cytotoxic potency towards MDA-MB-231 and DLD-1 cell lines with IC50 values comparable to a well-known anticancer drug cisplatin, which is generally used in clinical studies. Furthermore, a compound namely 1-(2-hydroxyethyl)-3-(2,3,4,5,6-pentamethylbenzyl)-1H-benzo[d]imidazol-3-ium bromide was found to be more cytotoxic activity in MDA-MB-231 cell line compared to cisplatin with following IC50 value of 7.59 +/- 0.68 mu M.
引用
收藏
页码:2903 / 2914
页数:12
相关论文
共 50 条
  • [1] Synthesis of aminoalkyl-substituted polymethoxychalcone derivatives and their antiproliferative activities against three human cancer cell lines
    Mingxia Chen
    Ling Shi
    Jiaqing Tang
    Qiuan Wang
    Chemical Research in Chinese Universities, 2016, 32 : 754 - 759
  • [2] Synthesis of Aminoalkyl-substituted Polymethoxychalcone Derivatives and Their Antiproliferative Activities Against Three Human Cancer Cell Lines
    Chen Mingxia
    Shi Ling
    Tang Jiaqing
    Wang Qiuan
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2016, 32 (05) : 754 - 759
  • [3] Synthesis, crystal structures, and catalytic activities of palladium imidazole complexes formed by 2-hydroxyethyl group cleavage
    Xu, Chen
    Li, Zhen
    Duan, Lu-Meng
    Wang, Zhi-Qiang
    Fu, Wei-Jun
    Hao, Xin-Qi
    Song, Mao-Ping
    TRANSITION METAL CHEMISTRY, 2012, 37 (04) : 373 - 378
  • [4] Synthesis, crystal structures, and catalytic activities of palladium imidazole complexes formed by 2-hydroxyethyl group cleavage
    Chen Xu
    Zhen Li
    Lu-Meng Duan
    Zhi-Qiang Wang
    Wei-Jun Fu
    Xin-Qi Hao
    Mao-Ping Song
    Transition Metal Chemistry, 2012, 37 : 373 - 378
  • [5] Antiproliferative activities of citrus flavonoids against six human cancer cell lines
    Manthey, JA
    Guthrie, N
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (21) : 5837 - 5843
  • [6] In vitro antiproliferative activity of palladium(II) complexes included within the β-cyclodextrin against various human tumor cell lines
    Jaimes, Nancy
    Salmen, Siham
    Carolina Colmenares, Melisa
    Virginia Mendoza, Rosa
    INVESTIGACION CLINICA, 2018, 59 (01): : 17 - 27
  • [7] Antiproliferative activities of parthenolide and golden feverfew extract against three human cancer cell lines
    Wu, Changqing
    Chen, Feng
    Rushing, James W.
    Wang, Xi
    Kim, Hyun-Jin
    Huang, George
    Haley-Zitlin, Vivian
    He, Guoqing
    JOURNAL OF MEDICINAL FOOD, 2006, 9 (01) : 55 - 61
  • [8] ANTIPROLIFERATIVE ACTIVITIES OF INTERFERONS AGAINST HUMAN BLADDER-CARCINOMA CELL-LINES INVITRO
    BORDEN, EC
    GROVEMAN, DS
    NASU, T
    REZNIKOFF, C
    BRYAN, GT
    JOURNAL OF UROLOGY, 1984, 132 (04): : 800 - 803
  • [9] Synthesis of new allyl palladium complexes bearing purine-based NHC ligands with antiproliferative and proapoptotic activities on human ovarian cancer cell lines
    Scattolin, Thomas
    Caligiuri, Isabella
    Canovese, Luciano
    Demitri, Nicola
    Gambari, Roberto
    Lampronti, Ilaria
    Rizzolio, Flavio
    Santo, Claudio
    Visentin, Fabiano
    DALTON TRANSACTIONS, 2018, 47 (38) : 13616 - 13630
  • [10] Investigation of fruit peel extracts as sources for compounds with antioxidant and antiproliferative activities against human cell lines
    Khonkarn, Ruttiros
    Okonogi, Siriporn
    Ampasavate, Chadarat
    Anuchapreeda, Songyot
    FOOD AND CHEMICAL TOXICOLOGY, 2010, 48 (8-9) : 2122 - 2129