Parietin: an efficient photo-screening pigment in vivo with good photosensitizing and photodynamic antibacterial effects in vitro

COMINI, LAURA R.; MORÁN VIEYRA, F. EDUARDO; MIGNONE, RICARDO A.; PÁEZ, PAULINA L.; LAURA MUGAS, M.; KONIGHEIM, BRENDA S.; CABRERA, JOSÉ L.; NÚÑEZ MONTOYA, SUSANA C.; BORSARELLI, CLAUDIO D.

Photochemical and Photobiological Sciences

ROYAL SOC CHEMISTRY

Año: 2017 vol. 16 p. 201 - 210

1474-905X

The photophysical, photoinduced pro-oxidant and antibacterial properties in vitro of the natural occurring parietin (PTN; 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthraquinone) were evaluated. PTN was extracted from the lichen identified as Teloschistes flavicans (Sw.) Norm. (Telochistaceae). Results indicate that in chloroform solution, PTN presents spectroscopic features corresponding to an excited-state intramolecular proton-transfer (ESIPT) state with partial keto-enol tautomerization. In argon-saturated solutions, the singlet excited state is poorly fluorescent (ΦF = 0.03), decaying by efficient intersystem crossing to an excited triplet state 3PTN*, as detected by laser-flash photolysis experiments. In the presence of triplet molecular oxygen, the 3PTN* was fully quenched producing singlet molecular oxygen (1O2) with a quantum yield of 0.69. In addition, in buffer solutions, PTN has the ability to also generate a superoxide radical anion (O2 ?-) in a human leukocyte model and its production was enhanced under UVA-Vis irradiation. Finally, the in vitro antibacterial capability of PTN in the dark and under UVA-Vis illumination was compared in microbial cultures of both Gram positive and negative bacteria. As a result, PTN showed promising photo-induced antibacterial activity through the efficient photosensitized generation of both 1O2 and O2 ?- species. Thus, we have demonstrated that PTN, an efficient photo-screening pigment in lichens, is also a good photosensitizer in solution with promising applications in antibacterial photodynamic therapy.