Will the Interactions of Some Platinum (II)-Based Drugs with B-Vitamins Reduce Their Therapeutic Effect in Cancer Patients? Comparison of Chemotherapeutic Agents such as Cisplatin, Carboplatin and Oxaliplatin-A Review

被引:14
作者
Szefler, Beata [1 ]
Czelen, Przemyslaw [1 ]
机构
[1] Nicolaus Copernicus Univ, Fac Pharm, Coll Med, Dept Phys Chem, Kurpinskiego 5, PL-85096 Bydgoszcz, Poland
关键词
cisplatin; carboplatin; oxaliplatin; platinum-based drugs; cancer treatment; vitamin B; MOLECULAR-MECHANISMS; CELLULAR ACCUMULATION; TRANSPORTER CTR1; DNA; BINDING; COMPLEXES; RESISTANCE; CELLS; RIBOFLAVIN; MANAGEMENT;
D O I
10.3390/ijms24021548
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
Pt (II) derivatives show anti-cancer activity by interacting with nucleobases of DNA, thus causing some spontaneous and non-spontaneous reactions. As a result, mono- and diaqua products are formed which further undergo complexation with guanine or adenine. Consequently, many processes are triggered, which lead to the death of the cancer cell. The theoretical and experimental studies confirm that such types of interactions can also occur with other chemical compounds. The vitamins from B group have a similar structure to the nucleobases of DNA and have aromatic rings with single-pair orbitals. Theoretical and experimental studies were performed to describe the interactions of B vitamins with Pt (II) derivatives such as cisplatin, oxaliplatin and carboplatin. The obtained results were compared with the values for guanine. Two levels of simulations were implemented at the theoretical level, namely, B3LYP/6-31G(d,p) with LANL2DZ bases set for platinum atoms and MN15/def2-TZVP. The polarizable continuum model (IEF-PCM preparation) and water as a solvent were used. UV-Vis spectroscopy was used to describe the drug-nucleobase and drug-B vitamin interactions. Values of the free energy (Delta G(r)) show spontaneous reactions with mono- and diaqua derivatives of cisplatin and oxaliplatin; however, interactions with diaqua derivatives are more preferable. The strength of these interactions was also compared. Carboplatin products have the weakest interaction with the studied structures. The presence of non-covalent interactions was demonstrated in the tested complexes. A good agreement between theory and experiment was also demonstrated.
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页数:19
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共 63 条
[1]   Chemotherapeutic agents for the treatment of metastatic breast cancer: An update [J].
Abotaleb, Mariam ;
Kubatka, Peter ;
Caprnda, Martin ;
Varghese, Elizabeth ;
Zolakova, Barbora ;
Zubor, Pavol ;
Opatrilova, Radka ;
Kruzliak, Peter ;
Stefanicka, Patrik ;
Busselberg, Dietrich .
BIOMEDICINE & PHARMACOTHERAPY, 2018, 101 :458-477
[2]   Platinum-DNA Interactions and Subsequent Cellular Processes Controlling Sensitivity to Anticancer Platinum Complexes [J].
Ahmad, Saeed .
CHEMISTRY & BIODIVERSITY, 2010, 7 (03) :543-566
[3]  
Alcindor T, 2011, CURR ONCOL, V18, P18
[4]  
[Anonymous], 2017, Contin. Updat. Proj. Expert Rep, P120, DOI [10.1007/s12082-007-0105-4, DOI 10.1007/S12082-007-0105-4]
[5]   Theoretical study of cisplatin binding to purine bases: Why does cisplatin prefer guanine over adenine? [J].
Baik, MH ;
Friesner, RA ;
Lippard, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :14082-14092
[6]   Modifications of DNA by platinum complexes - Relation to resistance of tumors to platinum antitumor drugs [J].
Brabec, V ;
Kasparkova, J .
DRUG RESISTANCE UPDATES, 2005, 8 (03) :131-146
[7]   Recognition and processing of cisplatin- and oxaliplatin-DNA adducts [J].
Chaney, SG ;
Campbell, SL ;
Bassett, E ;
Wu, YB .
CRITICAL REVIEWS IN ONCOLOGY HEMATOLOGY, 2005, 53 (01) :3-11
[8]   Cisplatin in cancer therapy: Molecular mechanisms of action [J].
Dasari, Shaloam ;
Tchounwou, Paul Bernard .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2014, 740 :364-378
[9]   Carboplatin: molecular mechanisms of action associated with chemoresistance [J].
de Sousa, Graziele Fonseca ;
Wlodarczyk, Samarina Rodrigues ;
Monteiro, Gisele .
BRAZILIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2014, 50 (04) :693-701
[10]   Particular aspects of platinum compounds used at present in cancer treatment [J].
Desoize, B ;
Madoulet, C .
CRITICAL REVIEWS IN ONCOLOGY HEMATOLOGY, 2002, 42 (03) :317-325