A new folate derivative with affinity to biomembranes – bis-decyl pteroic acid: synthesis, structural characterization and photochemical properties

FONSECA, JOSE; MARIA JOSÉ SOSA; GABRIELA PETROSELLI; ROSA ERRA-BALSELLS; MATÍAS I. QUINDT; ALEXANDER GREER; BONESI, SERGIO M.; GREER, EDYTA M.; THOMAS, ANDRÉS H.; MARIANA VIGNONI

Chicago

Conferencia; ACS FALL 2022; 2022

ACS

A bis-decylated pteroic acid photosensitizer has been synthesized and characterized. The compound name is decyl 4-(((2-amino-4-decyloxypteridin-6-yl)methyl)amino)benzoate and the synthesis was carried out in a reaction of 1-iododecane with pteroic acid and potassium carbonate in N,N-dimethylaniline (DMA). The decyl chain addition arises in a sequential manner, in which the mono-decyl compound is an intermediate and reacts rapidly to the bis-decyl product. Characterization data include 1D and 2D NMR, HPLC, UV-vis, mass spectrometry, and also will include data collected with density functional theory to compare the relative stabilities of various substituted bis-decylated pteroic acid regioisomers with the notion generating a gemini-type sensitizer surfactant to increase its lipophilicity for potential use in membrane localized photodynamics.alkyl 4-(((2-amino-4-alkoxypteridin-6-yl)methyl)amino)benzoatedecyl 4-(((2-amino-4-decyloxypteridin-6-yl)methyl)amino)benzoate