Bis(dimethylsulfoxide)carbonateplatinum(ii), a new synthon for a low-impact, versatile synthetic route to anticancer Pt carboxylates.
The work describes a new low-impact synthetic route to Pt(ii)-carboxylate complexes, a class of compounds provided with established anticancer activity. The process is based on the ligand substitution on [PtCO3(Me2SO-S)2] (), a new synthon that can be easily prepared in water with high yield, is stable as a solid, and is reactive in solution where all its ligands can be easily replaced. It reacts with acidic O-donors releasing CO2 as the only side-product, whose development also supplies a driving force toward the products. The substitution of carbonate led to new Pt-DMSO carboxylate complexes , while the total substitution of the ligands of complex gave new Pt-phosphino carboxylates in high yields. The X-ray crystal structures of complexes [Pt(d(-)-quinate-O,O')(Me2SO-S)2] (), [Pt(salicylate)(Me2SO-S)2] () and [Pt(salicylate)(PPh3)2] () were determined. The tests of the antiproliferative activity of complexes on two human tumoral cell lines, A2780 (cisplatin-sensitive) and SKOV-3 (cisplatin-resistant), showed that the PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) complexes were the most active on both cell lines.
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara, via Fossato di Mortara 17, 44121 Ferrara, Italy. bgp@unife.it.
Paola
P
Bergamini
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara, via Fossato di Mortara 17, 44121 Ferrara, Italy. bgp@unife.it.
Lorenza
L
Marvelli
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara, via Fossato di Mortara 17, 44121 Ferrara, Italy. bgp@unife.it.
Valeria
V
Ferretti
Dipartimento di Scienze della Vita e Biotecnologie, Sezione di Biochimica e Biologia Molecolare, Università degli Studi di Ferrara, Via Fossato di Mortara 74, 44121 Ferrara, Italy.
Chiara
C
Gemmo
Dipartimento di Scienze della Vita e Biotecnologie, Sezione di Biochimica e Biologia Molecolare, Università degli Studi di Ferrara, Via Fossato di Mortara 74, 44121 Ferrara, Italy.
Roberto
R
Gambari
Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Ferrara, via Fossato di Mortara 17, 44121 Ferrara, Italy. bgp@unife.it.
Yekatsiaryna
Y
Hushcha
Dipartimento di Scienze della Vita e Biotecnologie, Sezione di Biochimica e Biologia Molecolare, Università degli Studi di Ferrara, Via Fossato di Mortara 74, 44121 Ferrara, Italy.
Ilaria
I
Lampronti
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002254:Carbonates / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D004121:Dimethyl Sulfoxide / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy; D009944:Organoplatinum Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D002254:Carbonates; D002264:Carboxylic Acids; D009944:Organoplatinum Compounds; D004121:Dimethyl Sulfoxide