Synthesis, characterization, and photocleavage of bis-decyl pteroic acid: A folate derivative with affinity to biomembranes

JOSÉ L. FONSECA CASTRO; SOSA, MARÍA JOSÉ; PETROSELLI GABRIELA; ERRA BALSELLS ROSA; QUINDT MATIAS; GREER, ALEXANDER; GREER, EDYTA M.; BONESI, SERGIO M.; THOMAS ANDRÉS H.; VIGNONI MARIANA

Albuquerque

Encuentro; 41st American Society for Photobiology Biennial Meeting (ASP 2022); 2022

American Society for Photobiology

Here, we provide mechanistic insight to the photocleavage of a related compound of the folate family, pteroic acid. A bis-decyl chain derivative of pteroic acid was synthesized and its structural characterization is described. While folic acid undergoes a self-sensitized photocleavage in H2O, we hypothesized that a lipophilic pteroic acid will also undergo a photocleavage but in non-aqueous solution. Furthermore, density functional theory calculations were carried out to predict relative stabilities of hypothetical mono-, bis-, and tris-decylated pteroic acid derivatives and to help rationalize the regioselectivity of the bis-decyl pteroic acid product. Additionally, the lipophilicity of the bis-decyl pteroic acid confers the compound the ability to interact with biomembranes.