Synthesis and biological activity of novel bifunctional isoxazolidinyl polycyclic aromatic hydrocarbons.
This paper reports the synthesis and the biological properties of two novel pyrene-bearing isoxazolidinyl derivatives able to exhibit antitumor activity by DNA intercalation. The synthetic approach exploits a consolidated protocol based on 1,3-dipolar cycloaddition reaction. The intercalating properties have been determined by combining electrophoresis studies with molecular docking, while the antitumor activity has been evaluated over five carcinoma cell lines. The obtained compounds show also a good affinity towards silver cations; the presence of a 2-hydroxybenzyl appendage on the isoxazolidine ring ensures a good affinity and selectivity in the binding.
Dipartimento di Scienze del Farmaco, Università di Catania, Viale Andrea Doria 6, Catania 95125, Italy. arescifina@unict.it
Antonio
A
Rescifina
Chiara
C
Zagni
Giovanni
G
Romeo
Salvatore
S
Sortino
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002522:Chlorocebus aethiops; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014709:Vero Cells
D000970:Antineoplastic Agents; D007555:Isoxazoles; D011084:Polycyclic Aromatic Hydrocarbons