Synthesis and pharmacological evaluation of modified adenosines joined to mono-functional platinum moieties
The synthesis of four novel platinum complexes, bearing N6-(6-amino-hexyl)adenosine or a 1,6-di(adenosin-N6-yl)-hexane respectively, as ligands of mono-functional cisplatin or monochloro(ethylendiamine)platinum(II), is reported. The chemistry exploits the high affinity of the charged platinum centre...
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| Published in: | Molecules (Basel, Switzerland) Vol. 19; no. 7; pp. 9339 - 9353 |
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| Main Authors: | , , , , , , , , , , |
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| Language: | English |
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| Abstract | The synthesis of four novel platinum complexes, bearing N6-(6-amino-hexyl)adenosine or a 1,6-di(adenosin-N6-yl)-hexane respectively, as ligands of mono-functional 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. |
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| AbstractList | The synthesis of four novel platinum complexes, bearing N6-(6-amino-hexyl)adenosine or a 1,6-di(adenosin-N6-yl)-hexane respectively, as ligands of mono-functional 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. The synthesis of four novel platinum complexes, bearing N 6 -(6-amino-hexyl)adenosine or a 1,6-di(adenosin- N 6 -yl)-hexane respectively, as ligands of mono-functional 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. |
| Author | Oliviero, Giorgia Borbone, Nicola Costantino, Valeria D'Errico, Stefano Carnuccio, Rosa Piccialli, Vincenzo De Falco, Francesca Nici, Fabrizia Piccialli, Gennaro Pinto, Brunella Maiuri, Maria Chiara |
| AuthorAffiliation | 2 Dipartimento di Scienze Chimiche, Università degli Studi di Napoli “Federico II”, via Cintia, 21, 80126 Napoli, Italy; E-Mail: vinpicci@unina.it 3 INSERM U848, IGR, 39 rue C. Desmoulins, 94805 Villejuif, France 1 Dipartimento di Farmacia, Università degli Studi di Napoli “Federico II”, via D. Montesano, 49, 80131 Napoli, Italy; E-Mails: stefano.derrico@unina.it (S.D.); borbone@unina.it (N.B.); brunella.pinto87@gmail.com (B.P.); francesca.defalco@unina.it (F.D.F.); mariachiara.maiuri@unina.it (M.C.M.); rosa.carnuccio@unina.it (R.C.); valeria.costantino@unina.it (V.C.); fabrizia.nici@unina.it (F.N.); picciall@unina.it (G.P.) |
| AuthorAffiliation_xml | – name: 2 Dipartimento di Scienze Chimiche, Università degli Studi di Napoli “Federico II”, via Cintia, 21, 80126 Napoli, Italy; E-Mail: vinpicci@unina.it – name: 3 INSERM U848, IGR, 39 rue C. Desmoulins, 94805 Villejuif, France – name: 1 Dipartimento di Farmacia, Università degli Studi di Napoli “Federico II”, via D. Montesano, 49, 80131 Napoli, Italy; E-Mails: stefano.derrico@unina.it (S.D.); borbone@unina.it (N.B.); brunella.pinto87@gmail.com (B.P.); francesca.defalco@unina.it (F.D.F.); mariachiara.maiuri@unina.it (M.C.M.); rosa.carnuccio@unina.it (R.C.); valeria.costantino@unina.it (V.C.); fabrizia.nici@unina.it (F.N.); picciall@unina.it (G.P.) |
| Author_xml | – sequence: 1 givenname: Stefano surname: D'Errico fullname: D'Errico, Stefano email: stefano.derrico@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. stefano.derrico@unina.it – sequence: 2 givenname: Giorgia surname: Oliviero fullname: Oliviero, Giorgia email: golivier@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. golivier@unina.it – sequence: 3 givenname: Nicola surname: Borbone fullname: Borbone, Nicola email: borbone@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. borbone@unina.it – sequence: 4 givenname: Vincenzo surname: Piccialli fullname: Piccialli, Vincenzo email: vinpicci@unina.it organization: Dipartimento di Scienze Chimiche, Università degli Studi di Napoli "Federico II", via Cintia, 21, 80126 Napoli, Italy. vinpicci@unina.it – sequence: 5 givenname: Brunella surname: Pinto fullname: Pinto, Brunella email: brunella.pinto87@gmail.com organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. brunella.pinto87@gmail.com – sequence: 6 givenname: Francesca surname: De Falco fullname: De Falco, Francesca email: francesca.defalco@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. francesca.defalco@unina.it – sequence: 7 givenname: Maria Chiara surname: Maiuri fullname: Maiuri, Maria Chiara email: mariachiara.maiuri@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. mariachiara.maiuri@unina.it – sequence: 8 givenname: Rosa surname: Carnuccio fullname: Carnuccio, Rosa email: rosa.carnuccio@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. rosa.carnuccio@unina.it – sequence: 9 givenname: Valeria surname: Costantino fullname: Costantino, Valeria email: valeria.costantino@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. valeria.costantino@unina.it – sequence: 10 givenname: Fabrizia surname: Nici fullname: Nici, Fabrizia email: fabrizia.nici@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. fabrizia.nici@unina.it – sequence: 11 givenname: Gennaro surname: Piccialli fullname: Piccialli, Gennaro email: picciall@unina.it organization: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II", via D. Montesano, 49, 80131 Napoli, Italy. picciall@unina.it |
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| CitedBy_id | crossref_primary_10_1016_j_bioorg_2022_106325 crossref_primary_10_1002_ejoc_201700730 crossref_primary_10_1002_ejoc_201500998 crossref_primary_10_1016_j_ccr_2016_02_008 crossref_primary_10_3390_molecules20057951 crossref_primary_10_3390_pharmaceutics12070627 crossref_primary_10_1002_ejoc_201403648 crossref_primary_10_1016_j_ica_2016_01_033 crossref_primary_10_3390_ph13100284 |
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| Snippet | The synthesis of four novel platinum complexes, bearing N6-(6-amino-hexyl)adenosine or a 1,6-di(adenosin-N6-yl)-hexane respectively, as ligands of... The synthesis of four novel platinum complexes, bearing N 6 -(6-amino-hexyl)adenosine or a 1,6-di(adenosin- N 6 -yl)-hexane respectively, as ligands of... |
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| SubjectTerms | Adenosine Adenosine - analogs & derivatives Adenosine - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Cancer Cell Proliferation - drug effects Cell Survival - drug effects Chemotherapy cisplatin Contraindications Cytotoxicity Drug Screening Assays, Antitumor Humans Ligands MCF-7 Cells nucleosides platinum complexes Platinum Compounds - chemical synthesis Platinum Compounds - pharmacology Tumors |
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| Title | Synthesis and pharmacological evaluation of modified adenosines joined to mono-functional platinum moieties |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/24995920 https://www.proquest.com/docview/1548297402 https://search.proquest.com/docview/1543687189 https://pubmed.ncbi.nlm.nih.gov/PMC6271865 https://doaj.org/article/17d5314de7254d29a249ab32ee52e65d |
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