title: Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter.
abstract: In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have been performed, suggesting that all active compounds interact with FcyB through the formation of hydrogen bonds with Asn163, while the insertion of hydrophobic fragments at position 9 and N6 of 3-deazaadenine enhanced the inhibition.
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: Nikolaos
authors.initials: N
authors.lastname: Lougiakis
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: Efthymios-Spyridon
authors.initials: ES
authors.lastname: Gavriil
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: Markelos
authors.initials: M
authors.lastname: Kairis
authors.affiliation: Department of Biology, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.
authors.forename: Georgia
authors.initials: G
authors.lastname: Sioupouli
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: George
authors.initials: G
authors.lastname: Lambrinidis
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: Dimitra
authors.initials: D
authors.lastname: Benaki
authors.affiliation: Department of Biology, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece.
authors.forename: Emilia
authors.initials: E
authors.lastname: Krypotou
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Mikros
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.
authors.forename: Panagiotis
authors.initials: P
authors.lastname: Marakos
authors.affiliation: Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece. Electronic address: pouli@pharm.uoa.gr.
authors.forename: Nicole
authors.initials: N
authors.lastname: Pouli
authors.affiliation: Department of Biology, National and Kapodistrian University of Athens, Panepistimiopolis, Athens 15784, Greece. Electronic address: diallina@biol.uoa.gr.
authors.forename: George
authors.initials: G
authors.lastname: Diallinas
mesh_terms: D001233:Aspergillus nidulans / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D008024:Ligands; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D033702:Nucleobase Transport Proteins / Q000037:antagonists & inhibitors* / Q000378:metabolism; D011687:Purines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D008024:Ligands; D033702:Nucleobase Transport Proteins; D011687:Purines; C030985:purine
keywords: Aspergillus nidulans; Combiglide; Deazaadenine; Imidazo[4,5-c]pyridine; Purine transporters; Structure activity relationships