Synthesis, crystal structure and bio-macromolecular interaction studies of pyridine-based thiosemicarbazone and its Ni(II) and Cu(II) complexes

被引:40
作者
Basu, Arghya [1 ]
Thiyagarajan, Durairaj [2 ]
Kar, Chirantan [1 ]
Ramesh, Aiyagari [2 ]
Das, Gopal [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Gauhati, Assam, India
[2] Indian Inst Technol, Dept Biotechnol, Gauhati, Assam, India
关键词
BOVINE SERUM-ALBUMIN; TRANSITION-METAL-COMPLEXES; RESONANCE ENERGY-TRANSFER; TERMINAL N-SUBSTITUTION; SOLID-PHASE SYNTHESIS; CYTOTOXIC ACTIVITY; DNA-BINDING; ALDEHYDE THIOSEMICARBAZONES; COPPER-COMPLEXES; OXIDATIVE CYCLIZATION;
D O I
10.1039/c3ra40904j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new pyridine-based heterocyclic thiosemicarbazone ligand and its Ni(II) and Cu(II) complexes have been synthesized and characterized by structural, analytical and spectral methods. The mono-deprotonated anionic form of the ligand coordinates via NNS donor atoms to yield an octahedral Ni(II) complex and distorted square planar Cu(II) complex. UV-visible and fluorescence-based spectroscopic techniques revealed that both metal complexes interact with double stranded DNA via intercalation. A comparative assessment indicated that the Ni(II) complex displayed superior DNA binding. The interaction of these compounds with bovine serum albumin (BSA) suggested that the ligand and its Cu(II) complex quenched the intrinsic fluorescence of BSA in a static quenching process, whereas for the Ni(II) complex, fluorescence quenching of BSA was a combination of both static and collision/dynamic quenching processes. The quenching of the fluorescence of BSA is owing to energy transfer from the tryptophan residues of BSA to the compounds bound to BSA. Cytotoxicity tests based on the standard MTT assay revealed that the Cu(II) complex displayed prominent anti-proliferative activity against HeLa cells.
引用
收藏
页码:14088 / 14098
页数:11
相关论文
共 89 条
[61]   Synthesis, structure and biological evaluation of bis salicylaldehyde-4(N)-ethylthiosemicarbazone ruthenium(III) triphenylphosphine [J].
Prabhakaran, R. ;
Kalaivani, P. ;
Jayakumar, R. ;
Zeller, M. ;
Hunter, A. D. ;
Renukadevi, S. V. ;
Ramachandran, E. ;
Natarajan, K. .
METALLOMICS, 2011, 3 (01) :42-48
[62]   Formation of unusual ruthenium(III) carbonyl complex through ONS tricoordination of salicylaldehyde-N-phenylthiosemicarbazone [J].
Prabhakaran, Rathinasabapathi ;
Huang, Rui ;
Karvembu, Ramasamy ;
Jayabalakrishnan, Chinnasamy ;
Natarajan, Karuppannan .
INORGANICA CHIMICA ACTA, 2007, 360 (02) :691-694
[63]   Can geometry control the coordination behaviour of 2-hydroxy-1-naphthaldehyde-N(4)-phenylthiosemicarbazone? A study towards its origin [J].
Prabhakaran, Rathinasabapathi ;
Palaniappan, Kalaivani ;
Huang, Rui ;
Sieger, Monica ;
Kaim, Wolfgang ;
Viswanathamurthi, Periyasamy ;
Dallemer, Frederic ;
Natarajan, Karuppannan .
INORGANICA CHIMICA ACTA, 2011, 376 (01) :317-324
[64]   In vitro and in vivo evaluation of isatin-β-thiosemicarbazone and marboran against vaccinia and cowpox virus infections [J].
Quenelle, Debra C. ;
Keith, Kathy A. ;
Kern, Earl R. .
ANTIVIRAL RESEARCH, 2006, 71 (01) :24-30
[65]   Contribution to the SAR field of metallated and coordination complexes. Studies of the palladium and platinum derivatives with selected thiosemicarbazones as antitumoral drugs [J].
Quiroga, AG ;
Ranninger, CN .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (1-2) :119-133
[66]   Effect of N(4)-Phenyl Substitution in 2-Oxo-1,2-dihydroquinoline-3-carbaldehyde Semicarbazones on the Structure, DNA/Protein Interaction, and Antioxidative and Cytotoxic Activity of Cu(II) Complexes [J].
Raja, Duraisamy Senthil ;
Bhuvanesh, Nattamai S. P. ;
Natarajan, Karuppannan .
INORGANIC CHEMISTRY, 2011, 50 (24) :12852-12866
[67]   Biological evaluation of a novel water soluble sulphur bridged binuclear copper(II) thiosemicarbazone complex [J].
Raja, Duraisamy Senthil ;
Bhuvanesh, Nattamai S. P. ;
Natarajan, Karuppannan .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) :4584-4594
[68]   Effect of terminal N-substitution in 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazones on the mode of coordination, structure, interaction with protein, radical scavenging and cytotoxic activity of copper(II) complexes [J].
Raja, Duraisamy Senthil ;
Paramaguru, Ganesan ;
Bhuvanesh, Nattamai S. P. ;
Reibenspies, Joseph H. ;
Renganathan, Rajalingam ;
Natarajan, Karuppannan .
DALTON TRANSACTIONS, 2011, 40 (17) :4548-4559
[69]   Evaluation on the role of terminal N-substitution in 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazones on the biological properties of new water-soluble nickel(II) complexes [J].
Ramachandran, Eswaran ;
Raja, Duraisamy Senthil ;
Mike, Joshua L. ;
Wagner, Timothy R. ;
Zeller, Matthias ;
Natarajan, Karuppannan .
RSC ADVANCES, 2012, 2 (22) :8515-8525
[70]   Synthesis, characterization, crystal structure and DNA binding studies of Pd(II) complexes containing thiosemicarbazone and triphenylphosphine/triphenylarsine [J].
Ramachandran, Eswaran ;
Kalaivani, Palaniappan ;
Prabhakaran, Rathinasabapathi ;
Zeller, Matthias ;
Bartlett, Joshua H. ;
Adero, Philip O. ;
Wagner, Timothy R. ;
Natarajan, Karuppannan .
INORGANICA CHIMICA ACTA, 2012, 385 :94-99