Photochemical and photophysical study of bis-alkylated lumazine and pterin photosensitizers

MARÍA JOSÉ SOSA; MARIANA VIGNONI; MARÍA NOEL URRUTIA; MATÍAS I. QUINDT; SERGIO BONESI; DOBRUSHE DENBURG; ALEXANDER GREER; ANDRÉS H. THOMAS; EDYTA GREER

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Congreso; 49th Middle Atlantic Regional Meeting. American Chemical Society (ACS); 2021

A bis-decylated lumazine and pterin have been synthesized and characterized. Namely, bis-decyl chain 1,3-didecylpteridine-2,4(1H,3H)-dione and decyl 4-(((2-amino-4- (decyloxy)pteridin-6-yl)methyl)amino)benzoate conjugates were synthesized. The synthesis was carried out by nucleophilic substitution (SN2) reactions of 1-iododecane with lumazine and pteroic acid, in N,N-dimethylformamide (DMF) and N,N-dimethylaniline (DMA) solvent respectively. Decyl chain coupling arises in a sequential manner, without DMF or DMA condensation. Experimental data from NMR (1D and 2D), HPLC, UV-vis, fluorescence, as well as theoretical data (density functional theory) will be presented to compare the two bis-decylated sensitizers with the notion to add to strategies for increasing sensitizer lipophilicity for use in antimicrobial photodynamic inactivation and photodynamic therapy.