Iron(III) Catecholates for Cellular Imaging and Photocytotoxicity in Red Light

被引:32
作者
Basu, Uttara [1 ]
Pant, Ila [2 ]
Khan, Imran [2 ]
Hussain, Akhtar [1 ]
Kondaiah, Paturu [2 ]
Chakravarty, Akhil R. [1 ]
机构
[1] Indian Inst Sci, Dept Inorgan & Phys Chem, Bangalore 560012, Karnataka, India
[2] Indian Inst Sci, Dept Mol Reprod Dev & Genet, Bangalore 560012, Karnataka, India
关键词
apoptosis; bioinorganic chemistry; DNA cleavage; iron; photocytotoxicity; NEAR-IR LIGHT; DNA CLEAVAGE; COMPLEXES; LIGANDS; METAL; DIOXYGENASES; BLEOMYCIN; MECHANISM; THERAPY; BINDING;
D O I
10.1002/asia.201402207
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Iron(III) complexes [ Fe(L)(L') (NO3)]-in which L is phenyl-N, N-bis[(pyridin-2-yl) methyl]methanamine (1), (anthracen-9-yl)N, N-bis[(pyridin-2-yl) methyl] methanamine (2), (pyreny-1-yl)-N, N-bis[(pyridin- 2-yl) methyl] methanamine (3-5), and L' is catecholate (1-3), 4-tert-butyl catecholate (4), and 4-(2-aminoethyl)benzene- 1,2-diolate (5)-were synthesized and their photocytotoxic proper-ties examined. The five electron-paramagnetic complexes displayed a FeIII/ Fe-II redox couple near similar to 0.4 V versus a saturated calomel electrode (SCE) in DMF/0.1m tetrabutylammonium perchlorate (TBAP). They showed unpre-cedented photocytotoxicity in red light (600-720 nm) to give IC50-15 mm in various cell lines by means of apoptosis to generate reactive oxygen species. They were ingested in the nucleus of HeLa and HaCaT cells in 4 h, thereby interacting favorably with calf thymus (ct)-DNA and photocleaving pUC19 DNA in red light of 785 nm to form hydroxyl radicals.
引用
收藏
页码:2494 / 2504
页数:11
相关论文
共 52 条
[1]   Enhanced Antitumor Activity of the Photosensitizer meso-Tetra(N-methyl-4-pyridyl) Porphine Tetra Tosylate through Encapsulation in Antibody-Targeted Chitosan/Alginate Nanoparticles [J].
Abdelghany, Sharif M. ;
Schmid, Daniela ;
Deacon, Jill ;
Jaworski, Jakub ;
Fay, Francois ;
McLaughlin, Kirsty M. ;
Gormley, Julie A. ;
Burrows, James F. ;
Longley, Daniel B. ;
Donnelly, Ryan F. ;
Scott, Christopher J. .
BIOMACROMOLECULES, 2013, 14 (02) :302-310
[2]   Selective extradiol cleavage of catechol achieved in organized assemblies using [Fe(BPA)Cl3] (BPA = bis(pyridylmethyl)amine) [J].
Anitha, Natarajan ;
Palaniandavar, Mallayan .
DALTON TRANSACTIONS, 2010, 39 (05) :1195-1197
[3]  
[Anonymous], 2012, ANGEW CHEM, V124, P2712
[4]   INTERACTIONS AMONG IRON(II) BLEOMYCIN, LEWIS-BASES, AND DNA [J].
ANTHOLINE, WE ;
PETERING, DH ;
SARYAN, LA ;
BROWN, CE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1981, 78 (12) :7517-7520
[5]   Remarkable photocytotoxicity of curcumin in HeLa cells in visible light and arresting its degradation on oxovanadium(IV) complex formation [J].
Banerjee, Samya ;
Prasad, Puja ;
Hussain, Akhtar ;
Khan, Imran ;
Kondaiah, Paturu ;
Chakravarty, Akhil R. .
CHEMICAL COMMUNICATIONS, 2012, 48 (62) :7702-7704
[6]   Terpyridine Oxovanadium(IV) Complexes of Phenanthroline Bases for Cellular Imaging and Photocytotoxicity in HeLa Cells [J].
Banik, Bhabatosh ;
Sasmal, Pijus K. ;
Roy, Sovan ;
Majumdar, Ritankar ;
Dighe, Rajan R. ;
Chakravarty, Akhil R. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (09) :1425-1435
[7]   Photochemistry of organic iron(III) complexing ligands in oceanic systems [J].
Barbeau, Katherine .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2006, 82 (06) :1505-1516
[8]   Photodynamic Effect in Near-IR Light by a Photocytotoxic Iron(III) Cellular Imaging Agent [J].
Basu, Uttara ;
Khan, Imran ;
Hussain, Akhtar ;
Kondaiah, Paturu ;
Chakravarty, Akhil R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (11) :2658-2661
[9]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[10]   POTASSIUM MONOPERSULFATE AND A WATER-SOLUBLE MANGANESE PORPHYRIN COMPLEX, [MN(TMPYP)](OAC)5, AS AN EFFICIENT REAGENT FOR THE OXIDATIVE CLEAVAGE OF DNA [J].
BERNADOU, J ;
PRATVIEL, G ;
BENNIS, F ;
GIRARDET, M ;
MEUNIER, B .
BIOCHEMISTRY, 1989, 28 (18) :7268-7275