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

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

Photochemistry Photobiology

Wiley VCH

Año: 2023 vol. 99 p. 593 - 604

1751-1097

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.