Platinum(II) Oxalato Complexes Involving Adenosine-Based N-Donor Ligands: Synthesis, Characterization and Cytotoxicity Evaluation

被引:10
作者
Starha, Pavel [1 ]
Popa, Igor [1 ]
Travnicek, Zdenek [1 ]
机构
[1] Palacky Univ, Reg Ctr Adv Technol & Mat, Dept Inorgan Chem, Fac Sci, CZ-77146 Olomouc, Czech Republic
关键词
platinum(II) complexes; oxalato complexes; N6-benzyladenosine derivatives; multinuclear NMR; antitumor activity; DFT calculations; IN-VITRO; X-RAY; BIOLOGICAL-ACTIVITY; CRYSTAL-STRUCTURES; BASIS-SET; DERIVATIVES; SPECTROSCOPY; MECHANISM; CISPLATIN; KINETICS;
D O I
10.3390/molecules19033832
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 one-step synthetic procedure using the reaction of potassium bis(oxalato)platinate(II) with the corresponding N6-benzyladenosine derivative (nL) provided the [Pt(ox)(nL)(2)]center dot 1.5H(2)O oxalato (ox) complexes 1-5, involving the nL molecules as monodentate coordinated N-donor ligands. The complexes were thoroughly characterized by elemental analysis, multinuclear (H-1, C-13, N-15, Pt-195) and two dimensional NMR, infrared and Raman spectroscopy, and mass spectrometry, proving their composition and purity as well as coordination of nL through the N7 atom of the purine moiety. Geometry of [Pt(ox)(4FL)(2)] (5) was optimized at the B3LYP/LANLTZ/6-311G** level of theory. The complexes were screened for their in vitro cytotoxicity against two human cancer cell lines (HOS osteosarcoma and MCF7 breast adenocarcinoma), but they did not show any effect up to the concentration of 50.0 mu M (compounds 1, 2) or 20.0 mu M (compounds 3-5).
引用
收藏
页码:3832 / 3847
页数:16
相关论文
共 38 条
[1]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[2]   Clinical anticancer drug development: targeting the cyclin-dependent kinases [J].
Benson, C ;
Kaye, S ;
Workman, P ;
Garrett, M ;
Walton, M ;
de Bono, J .
BRITISH JOURNAL OF CANCER, 2005, 92 (01) :7-12
[3]   Insights into the mechanism of action of platinum anticancer drugs from multinuclear NMR spectroscopy [J].
Berners-Price, Susan J. ;
Ronconi, Luca ;
Sadler, Peter J. .
PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 2006, 49 (01) :65-98
[4]   MULTINUCLEAR NMR-STUDIES AND THE KINETICS OF FORMATION OF PLATINUM(II) - ADENINE-NUCLEOTIDE COMPLEXES [J].
BOSE, RN ;
CORNELIUS, RD ;
VIOLA, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4403-4408
[5]   Structural (X-ray), spectral (FT-IR and Raman) and quantum chemical investigations of a series of 6-benzylaminopurine derivatives [J].
Cajan, Michal ;
Travnicek, Zdenek .
JOURNAL OF MOLECULAR STRUCTURE, 2011, 994 (1-3) :350-359
[6]  
Cleare MJ., 1973, BIOINORG CHEM, V2, P187
[7]   Preparation, biological activity and endogenous occurrence of N6-benzyladenosines [J].
Dolezal, Karel ;
Popa, Igor ;
Hauserova, Eva ;
Spichal, Lukas ;
Chakrabarty, Kuheli ;
Novak, Ondrej ;
Krystof, Vladimir ;
Voller, Jiri ;
Holub, Jan ;
Strnad, Miroslav .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (11) :3737-3747
[8]   In Vitro Cytotoxic-Active Platinum(II) Complexes Derived from Carboplatin and Involving Purine Derivatives [J].
Dvorak, Lukas ;
Popa, Igor ;
Starha, Pavel ;
Travnicek, Zdenek .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (22) :3441-3448
[9]  
Feller D, 1996, J COMPUT CHEM, V17, P1571, DOI 10.1002/jcc.9
[10]   ADDUCTS OF THE ANTITUMOR DRUG CIS-DIAMMINEDICHLOROPLATINUM(II) WITH DNA - FORMATION, IDENTIFICATION, AND QUANTITATION [J].
FICHTINGERSCHEPMAN, AMJ ;
VANDERVEER, JL ;
DENHARTOG, JHJ ;
LOHMAN, PHM ;
REEDIJK, J .
BIOCHEMISTRY, 1985, 24 (03) :707-713