Synthesis and Pharmacological Evaluation of Modified Adenosines Joined to Mono-Functional Platinum Moieties

被引:9
作者
D'Errico, Stefano [1 ]
Oliviero, Giorgia [1 ]
Borbone, Nicola [1 ]
Piccialli, Vincenzo [2 ]
Pinto, Brunella [1 ]
De Falco, Francesca [1 ]
Maiuri, Maria Chiara [1 ,3 ]
Carnuccio, Rosa [1 ]
Costantino, Valeria [1 ]
Nici, Fabrizia [1 ]
Piccialli, Gennaro [1 ]
机构
[1] Univ Naples Federico II, Dipartimento Farm, I-80131 Naples, Italy
[2] Univ Naples Federico II, Dipartimento Sci Chim, I-80126 Naples, Italy
[3] INSERM, U848, IGR, F-94805 Villejuif, France
关键词
platinum complexes; nucleosides; cisplatin; chemotherapy; SOLID-PHASE SYNTHESIS; DNA-BINDING; COMPLEXES; CISPLATIN; CYTOTOXICITY; ANALOGS; RIBOSE; REACTIVITY; LIGANDS; DESIGN;
D O I
10.3390/molecules19079339
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
The synthesis of four novel platinum complexes, bearing N-6-(6-aminohexyl) adenosine or a 1,6-di(adenosin-N-6-yl)-hexane respectively, as ligands of monofunctional cisplatin or monochloro(ethylendiamine) platinum(II), is reported. The chemistry exploits the high affinity of the charged platinum centres towards the N7 position of the adenosine base system and a primary amine of an alkyl chain installed on the C6 position of the purine. The cytotoxic behaviour of the synthesized complexes has been studied in A549 adenocarcinomic human alveolar basal epithelial and MCF7 human breast adenocarcinomic cancer cell lines, in order to investigate their effects on cell viability and proliferation.
引用
收藏
页码:9339 / 9353
页数:15
相关论文
共 49 条
[1]   Platinum group antitumor chemistry: Design and development of new anticancer drugs complementary to cisplatin [J].
Abu-Surrah, AS ;
Kettunen, M .
CURRENT MEDICINAL CHEMISTRY, 2006, 13 (11) :1337-1357
[2]   SYNTHESIS OF BRIDGED DINUCLEOSIDES [J].
AGATHOCLEOUS, DC ;
PAGE, PCB ;
COSSTICK, R ;
GALPIN, IJ ;
MCLENNAN, AG ;
PRESCOTT, M .
TETRAHEDRON, 1990, 46 (06) :2047-2058
[3]   Development of organometallic (organo-transition metal) pharmaceuticals [J].
Allardyce, CS ;
Dorcier, A ;
Scolaro, C ;
Dyson, PJ .
APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (01) :1-10
[4]   Cytotoxicity, DNA binding, and reactivity against nucleosides of platinum (II) and (IV) spermine compounds [J].
AmoOchoa, P ;
Gonzalez, VM ;
Perez, JM ;
Masaguer, JR ;
Alonso, C ;
NavarroRanninger, C .
JOURNAL OF INORGANIC BIOCHEMISTRY, 1996, 64 (04) :287-299
[5]   Mechanistic insight into the cellular uptake and processing of cisplatin 30 years after its approval by FDA [J].
Arnesano, Fabio ;
Natile, Giovanni .
COORDINATION CHEMISTRY REVIEWS, 2009, 253 (15-16) :2070-2081
[6]   Dynamic processes in platinum(II)-adenosine complexes.: Preparation, NMR spectroscopic characterisation and crystal structure of isomeric PtII(dien)-adenosine complexes [J].
Arpalahti, J ;
Klika, KD ;
Sillanpaa, R ;
Kivekas, R .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (08) :1397-1402
[7]   Clinical overview on Lipoplatin™: a successful liposomal formulation of cisplatin [J].
Boulikas, Teni .
EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2009, 18 (08) :1197-1218
[8]   Targeted delivery of platinum-based anticancer complexes [J].
Butler, Jennifer S. ;
Sadler, Peter J. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2013, 17 (02) :175-188
[9]   Synthesis and in vitro antitumor activity of oligonucleotide-tethered and related platinum complexes [J].
Cai, LS ;
Lim, K ;
Ren, S ;
Cadena, RS ;
Beck, WT .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (18) :2959-2965
[10]   Design, modeling, synthesis and biological activity evaluation of camptothecin-linked platinum anticancer agents [J].
Cincinelli, Raffaella ;
Musso, Loana ;
Dallavalle, Sabrina ;
Artali, Roberto ;
Tinelli, Stella ;
Colangelo, Donato ;
Zunino, Franco ;
De Cesare, Michelandrea ;
Beretta, Giovanni Luca ;
Zaffaroni, Nadia .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 63 :387-400