Synthesis, characterization, DNA interactions and antiproliferative activity on glioblastoma of iminopyridine platinum(II) chelate complexes

被引:10
作者
Posadas, Inmaculada [1 ]
Alonso-Moreno, Carlos [2 ]
Bravo, Ivan [3 ]
Carrillo-Hermosilla, Fernando [4 ]
Garzon, Andres [3 ]
Villaseca, Noemi [3 ]
Lopez-Solera, Isabel [4 ]
Albaladejo, Jose [4 ,5 ,6 ]
Cena, Valentin [7 ]
机构
[1] Univ Castilla La Mancha, Unidad Assoc Neurodeath CSIC UCIM, Fac Farm, Dept Ciencias Med, Campus Univ Albacate, Albacate 02071, Spain
[2] Univ Castilla La Mancha, Fac Farm, Dept Quim Inorgan Organ Bioquim, Campus Univ Albacate, Albacate 02071, Spain
[3] Univ Castilla La Mancha, Fac Farm, Dept Quim & Fis, Campus Univ Albacate, Albacate 02071, Spain
[4] Univ Castilla La Mancha, Fac Cienctas Technol Quim, Dept Quim Inorgan Organ Bio, Campus Univ Cludard Real, Cludard Real 13071, Spain
[5] Univ Castilla La Mancha, Fac Ciencias Technol Quim, Dept Quim & Fis, Campus Univ Cludard Real, Cludard Real 13071, Spain
[6] Univ Castilla La Mancha, Unidad Assoc Neurodeath CSIC UCIM, Fac Med, Dept Ciencias med, Campus Univ Albacate, Albacete 02071, Spain
[7] Inst Salud Carlos III, CIBERNED, Madrid, Spain
关键词
Glioblastoma; DNA-binding; Cisplatin derivatives; OF-THE-ART; CROSS-LINKING; PHASE-II; LOG-P; CISPLATIN; CELLS; LIGAND; BINDING; AGENTS; PALLADIUM(II);
D O I
10.1016/j.jinorgbio.2016.11.032
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of iminopyridine platinum chelate compounds has been prepared and characterized by NMR spectroscopy and single-crystal X-ray diffraction. The complexes were evaluated in C6 tumoral cells as an in vitro model for glioblastoma multiforme. The DNA-binding properties of these complexes were studied by UV-Vis absorption and fluorescence spectroscopy and Density Functional Theory calculations were performed in an effort to rationalize the observed properties at the molecular level. The most promising drug candidate displayed a similar potency in inducing cell death to the clinically used reference compound and showed significant inhibition of glioblastoma cell proliferation. Moreover, this compound had a safer profile than cisplatin on non-tumoral cells. (C) 2016 Elsevier Inc. All rights reserved.
引用
收藏
页码:46 / 54
页数:9
相关论文
共 82 条
[1]   Antiglioma activity of 2,2′:6′,2"-terpyridineplatinum(II) complexes in a rat model -: Effects on cellular redox metabolism [J].
Ahmadi, R ;
Urig, S ;
Hartmann, M ;
Helmke, BM ;
Koncarevic, S ;
Allenberger, B ;
Kienhoefer, C ;
Neher, M ;
Steiner, HH ;
Unterberg, A ;
Herold-Mende, C ;
Becker, K .
FREE RADICAL BIOLOGY AND MEDICINE, 2006, 40 (05) :763-778
[2]  
[Anonymous], 1997, SADABS VERSION 2 03
[3]  
[Anonymous], 1997, SAINT NT VER 6 04 SA
[4]  
[Anonymous], 2013, SUPRAMOLECULAR SYSTE
[5]  
[Anonymous], 2000, BRUK AXS SHELXTL VER
[6]   Synthesis, structural characterization and cell death-inducing effect of novel palladium(II) and platinum(II) saccharinate complexes with 2-(hydroxymethyl)pyridine and 2-(2-hydroxyethyl) pyridine on cancer cells in vitro [J].
Ari, Ferda ;
Aztopal, Nazlihan ;
Icsel, Ceyda ;
Yilmaz, Veysel T. ;
Guney, Emel ;
Buyukgungor, Orhan ;
Ulukaya, Engin .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (21) :6427-6434
[7]   A Novel Platinum-Maurocalcine Conjugate Induces Apoptosis of Human Glioblastoma Cells by Acting through the ROS-ERK/AKT-p53 Pathway [J].
Aroui, Sonia ;
Dardevet, Lucie ;
Ben Ajmia, Wafa ;
de Boisvilliers, Madryssa ;
Perrin, Florian ;
Laajimi, Amel ;
Boumendjel, Ahcene ;
Kenani, Abderraouf ;
Muller, Jean Marc ;
De Waard, Michel .
MOLECULAR PHARMACEUTICS, 2015, 12 (12) :4336-4348
[8]   Bis(acridinylthiourea)platinum(II) Complexes: Synthesis, DNA affinity, and biological activity in ghoblastoma cells [J].
Augustus, TM ;
Anderson, J ;
Hess, SM ;
Bierbach, U .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (05) :855-858
[9]  
Basolo F, 2002, MODERN COORDINATION CHEMISTRY: THE LEGACY OF JOSEPH CHATT, P313, DOI 10.1039/9781847551481-00313
[10]   Cisplatin, oxaliplatin, and carboplatin unequally inhibit in vitro mRNA translation [J].
Becker, Jonas Philipp ;
Weiss, Johanna ;
TheileDepartment, Dirk .
TOXICOLOGY LETTERS, 2014, 225 (01) :43-47