Guanine-based amphiphiles: synthesis, ion transport properties and biological activity. Issue 5 (1st March 2015)

• Record Type: Journal Article
• Authors: Musumeci, Domenica; Irace, Carlo; Santamaria, Rita; Milano, Domenico; Tecilla, Paolo; Montesarchio, Daniela
• Is Part Of: Bioorganic & medicinal chemistry. Volume 23:Issue 5(2015)
• Page Start: 1149
• Page End: 1156
• Publication Date: 2015-03-01
• Subjects: AcOEt ethyl acetate -- Boc tert-butoxycarbonyl -- Boc2O Boc anhydride -- DCC dicyclohexylcarbodiimide -- DIAD diisopropylazodicarboxylate -- DMAP 4-(N, N-dimethylamino)pyridine -- DMF N, N-dimethylformamide -- PPh3 triphenylphosphine -- tBu tert-butyl -- TEA triethylamine -- TFA trifluoroacetic acid -- THF tetrahydrofuran; Guanine derivatives -- Amphiphiles -- Synthetic ionophores -- In vitro bioactivity tests; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2014.12.055
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: A novel guanine analog with high ionophoric and antiproliferative activity. Abstract: Novel amphiphilic guanine derivatives, here namedGua1 andGua2, have been prepared through few, simple and efficient synthetic steps. In ion transport experiments through phospholipid bilayers, carried out to evaluate their ability to mediate H + transport, Gua2 showed high activity. When this compound was investigated for ion-selective transport activities, no major differences were observed in the behaviour with cations while, in the case of anions, selective activity was observed in the series I − > Br − > Cl − > F − . The bioactivity of these guanine analogues has been evaluated on a panel of human tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays, showing a relevant antiproliferative profile forGua2 .