Synthesis and Evaluation of the Antitumor Properties of a Small Collection of PtII Complexes with 7-Deazaadenosine as Scaffold

被引:10
作者
D'Errico, Stefano [1 ,2 ]
Borbone, Nicola [1 ,2 ]
Piccialli, Vincenzo [3 ]
Di Gennaro, Elena [4 ]
Zotti, Andrea [4 ]
Budillon, Alfredo [4 ]
Vitagliano, Carlo [4 ]
Piccialli, Ilaria [5 ]
Oliviero, Giorgia [2 ,6 ]
机构
[1] Univ Napoli Federico II, Dipartimento Farm, Via Domenico Montesano 49, I-80131 Naples, Italy
[2] Univ Milano Bicocca, Ctr Syst Biol, SYSBIO IT, Milan, Italy
[3] Univ Napoli Federico II, Dipartimento Sci Chim, Via Cinthia 4, I-80126 Naples, Italy
[4] Fdn G Pascale IRCCS, Ist Nazl Tumori, Expt Pharmacol Unit, Via Mariano Semmola 52, I-80131 Naples, Italy
[5] Univ Napoli Federico II, Div Farmacol, Dipartimento Neurosci Sci Riprod & Odontostomatol, Scuola Med, Via Sergio Pansini 5, I-80131 Naples, Italy
[6] Univ Napoli Federico II, Dipartimento Med Mol & Biotecnol Med, Via Sergio Pansini 5, I-80131 Naples, Italy
关键词
Antitumor agents; Platinum; Nucleosides; Antiproliferative activity; SOLID-PHASE SYNTHESIS; PHARMACOLOGICAL EVALUATION; BIOLOGICAL EVALUATION; NATURAL-PRODUCTS; CANCER; DRUGS; ANALOGS; RIBOSE; DESIGN; NUCLEOSIDE;
D O I
10.1002/ejoc.201700730
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report on the synthesis and evaluation of the preliminary antitumor properties of a small collection of platinum(II) complexes in which a cisplatin-like unit is tethered to 7-deazaadenosine through linear alkyl chains (from two to six carbon atoms) installed at the purine C6 position. The complexation was performed by exploiting the reactivity of the bi-dentate amino ligands (R)- and (S)-2,3-diaminopropanoic acids (DAPA) attached to the end of the alkyl chain spacer. By varying the length of the alkyl chain and the chirality of the DAPA moiety we obtained 10 novel nucleoside-platinum complexes, the anticancer properties of which have been evaluated against the A549 and Cal27 human cancer cell lines.
引用
收藏
页码:4935 / 4947
页数:13
相关论文
共 57 条
[1]   BIOLOGICAL + BIOCHEMICAL PROPERTIES OF ANALOGUE ANTIBIOTIC TUBERCIDIN [J].
ACS, G ;
MORI, M ;
REICH, E .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1964, 52 (02) :493-+
[2]   Anticancer drugs from nature - natural products as a unique source of new microtubule-stabilizing agents [J].
Altmann, Karl-Heinz ;
Gertsch, Juerg .
NATURAL PRODUCT REPORTS, 2007, 24 (02) :327-357
[3]   The state-of-play and future of platinum drugs [J].
Apps, Michael G. ;
Choi, Eugene H. Y. ;
Wheate, Nial J. .
ENDOCRINE-RELATED CANCER, 2015, 22 (04) :R219-R233
[4]   Lipases, liposomes and lipid-prodrugs [J].
Arouri, Ahmad ;
Hansen, Anders Hojgaard ;
Rasmussen, Thomas Elmelund ;
Mouritsen, Ole G. .
CURRENT OPINION IN COLLOID & INTERFACE SCIENCE, 2013, 18 (05) :419-431
[5]   Furo[2,3-d]pyrimidine based derivatives as kinase inhibitors and anticancer agents [J].
Aziz, Marwa A. ;
Serya, Rabah A. T. ;
Lasheen, Deena S. ;
Abouzid, Khaled A. M. .
FUTURE JOURNAL OF PHARMACEUTICAL SCIENCES, 2016, 2 (01) :1-8
[6]   Synthesis, characterization and DNA binding activity of PtCl2[DMSO][N4[N-3(4-pyridylmethyl)thymidine]] [J].
Chen, Jun ;
Li, Kaiyu ;
Swavey, Shawn ;
Church, Kevin M. .
INORGANICA CHIMICA ACTA, 2016, 444 :76-80
[7]  
Chu C.K., 2003, Antiviral Nucleosides: Chiral Synthesis and Chemotherapy
[8]   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
[9]  
Coluccia M, 1995, Met Based Drugs, V2, P249, DOI 10.1155/MBD.1995.249
[10]   Synthesis and Evaluation of the Antiproliferative Properties of a Tethered Tubercidin-Platinum(II) Complex [J].
D'Errico, Stefano ;
Oliviero, Giorgia ;
Borbone, Nicola ;
Di Gennaro, Elena ;
Zotti, Andrea Ilaria ;
Budillon, Alfredo ;
Cerullo, Vincenzo ;
Nici, Fabrizia ;
Mayol, Luciano ;
Piccialli, Vincenzo ;
Piccialli, Gennaro .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (34) :7550-7556