Short metal-metal separations and in vitro anticancer studies of a new dinuclear silver(I)-N-heterocyclic carbene complex of para-xylyl-linked bis-benzimidazolium salt

被引:50
|
作者
Iqbal, Muhammad Adnan [1 ]
Haque, Rosenani A. [1 ]
Budagumpi, Srinivasa [1 ]
Ahamed, Mohamed B. Khadeer [2 ]
Majid, Amin M. S. Abdul [2 ]
机构
[1] Univ Sains Malaysia, Sch Chem Sci, Usm 11800, Penang, Malaysia
[2] Univ Sains Malaysia, Sch Pharmaceut Sci, EMAN Res & Testing Lab, Usm 11800, Penang, Malaysia
关键词
Ag-Ag separation; Ag(I)-carbene complex; N-heterocyclic carbene; HCT 116 cancer cells; HL 60 cancer cells; SILVER(I) COMPLEXES; CRYSTAL-STRUCTURES; SUBSTITUTED IMIDAZOL-2-YLIDENES; GOLD(I); AG(I); CYTOTOXICITY;
D O I
10.1016/j.inoche.2012.11.013
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new benzyl-substituted bis-benzimidazolium derivative featuring a para-xylene spacer (1) has been prepared. Reaction of I with Ag2O in stoichiometric ratio followed by metathesis with KPF6 yielded a dinuclear silver-carbene complex 2. The benzimidazolium ligands in 2 are arranged in a head-to-head fashion (2:2), spanning a short Ag-Ag separation of 3.10(6) angstrom between two complex units with the other Ag center of each unit remaining uninteracted. Molecular structure of complex 2 is elucidated by single crystal X-ray diffraction method. Both, 1 and 2, were tested for their potential antiproliferative activity against human colorectal carcinoma (HCT 116) and human leukemia (HL 60) cell lines. Almost similar effects were found for both the cell lines; however, complex 2 displayed more specificity and nearly six fold higher anticancer activity compared to 1 toward both the cell lines. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:64 / 69
页数:6
相关论文
共 16 条
  • [1] Synthesis and anticancer activity of para-xylyl linked bis-benzimidazolium salts and respective Ag(I) N-heterocyclic carbene complexes
    Iqbal, Muhammad Adnan
    Haque, Rosenani A.
    Ahamed, Mohamed B. Khadeer
    Majid, A. M. S. Abdul
    Al-Rawi, Sawsan S.
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (05) : 2455 - 2466
  • [2] Synthesis and anticancer activity of para-xylyl linked bis-benzimidazolium salts and respective Ag(I) N-heterocyclic carbene complexes
    Muhammad Adnan Iqbal
    Rosenani A. Haque
    Mohamed B. Khadeer Ahamed
    A. M. S. Abdul Majid
    Sawsan S. Al-Rawi
    Medicinal Chemistry Research, 2013, 22 : 2455 - 2466
  • [3] A new dinuclear Ag(I)-N-heterocyclic carbene complex derived from para-xylyl linked bis-imidazolium salt: synthesis, crystal structure, and in vitro anticancer studies
    Haque, Rosenani A.
    Nasri, Siti Fatimah
    Iqbal, Muhammad Adnan
    JOURNAL OF COORDINATION CHEMISTRY, 2013, 66 (15) : 2679 - 2692
  • [4] Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II)
    Haque, Rosenani A.
    Iqbal, Muhammad Adnan
    Asekunowo, Patrick
    Majid, A. M. S. Abdul
    Ahamed, Mohamed B. Khadeer
    Umar, Muhammad Ihtisham
    Al-Rawi, Sawsan S.
    Al-Suede, Fouad Saleih R.
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (10) : 4663 - 4676
  • [5] Synthesis, structure, anticancer, and antioxidant activity of para-xylyl linked bis-benzimidazolium salts and respective dinuclear Ag(I) N-heterocyclic carbene complexes (Part-II)
    Rosenani A. Haque
    Muhammad Adnan Iqbal
    Patrick Asekunowo
    A. M. S. Abdul Majid
    Mohamed B. Khadeer Ahamed
    Muhammad Ihtisham Umar
    Sawsan S. Al-Rawi
    Fouad Saleih R. Al-Suede
    Medicinal Chemistry Research, 2013, 22 : 4663 - 4676
  • [6] Synthesis, characterization and anti-proliferative activity of propylene linked bis-benzimidazolium salts and their respective dinuclear Silver(I)-N-heterocyclic carbene complexes
    Hussaini, Sunusi Y.
    Haque, Rosenani A.
    Asekunowo, Patrick O.
    Majid, A. M. S. Abdul
    Agha, M. Taleb
    Razali, Mohd. R.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 840 : 56 - 62
  • [7] Binuclear meta-xylyl-linked Ag(I)-N-heterocyclic carbene complexes of N-alkyl/aryl-alkyl-substituted bis-benzimidazolium salts: synthesis, crystal structures and in vitro anticancer studies
    Haque, Rosenani A.
    Iqbal, Muhammad Adnan
    Budagumpi, Srinivasa
    Ahamed, Mohamed B. Khadeer
    Majid, Amin M. S. Abdul
    Hasanudin, Noorhafizah
    APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (04) : 214 - 223
  • [8] Tetra N-heterocyclic carbene dinuclear silver(I) complexes as potential anticancer agents: Synthesis and in vitro anticancer studies
    Fatima, Tabinda
    Haque, Rosenani A.
    Iqbal, Muhammad Adnan
    Ahmad, Ashfaq
    Hassan, Loiy Elsir Ahmed
    Taleb-Agha, Mohamad
    Ahamed, Mohamed B. Khadeer
    Majid, A. M. S. Abdul
    Razali, Mohd. R.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 853 : 122 - 135
  • [9] Synthesis, structures and antibacterial studies of non-functionalized and nitrile-functionalized bis-benzimidazolium salts and respective dinuclear silver(I)-N-heterocyclic carbene complexes
    Haziz, Umie F. M.
    Haque, Rosenani A.
    Amirul, A. A.
    Shaheeda, N.
    Razali, Mohd R.
    POLYHEDRON, 2016, 117 : 628 - 636
  • [10] Potential of silver against human colon cancer: (synthesis, characterization and crystal structures of xylyl (Ortho, meta, & Para) linked bis-benzimidazolium salts and Ag(I)-NHC complexes: In vitro anticancer studies)
    Iqbal, Muhammad Adnan
    Haque, Rosenani A.
    Nasri, Siti Fatimah
    Majid, A. M. S. Abdul
    Ahamed, Mohamed B. Khadeer
    Farsi, Elham
    Fatima, Tabinda
    CHEMISTRY CENTRAL JOURNAL, 2013, 7