Alkylation converts riboflavin into an efficient photosensitizer of phospholipid membranes

SOSA, MARÍA J.; FONSECA JOSÉ L.; SAKAYA; URRUTIA, MARÍA; PETROSELLI GABRIELA; ERRA BALSELLS ROSA; QUINDT, MATIAS; BONESI SERGIO M; COSA GONZALO; VIGNONE MARIANA; THOMAS A.

BIOMEMBRANES

Elsevier

Lugar: Amsterdam; Año: 2023 vol. 1865 p. 184155 - 184156

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.