@misc{10481/88731,
year = {2023},
url = {https://hdl.handle.net/10481/88731},
abstract = {Harmaline (1) and harmalol (2) represent two 3,4-dihydro-β-carboline (DHβCs) most frequently reported in a vast number
of living systems. Fundamental aspects including the photosensitizing properties, cellular uptake, as well as the cyto- and
phototoxicity of 1 and 2 were investigated herein. The molecular basis underlying the investigated processes are elucidated.
Data reveal that both alkaloids show a distinctive pattern of extracellular DNA photodamage. Compound 1 induces a DNA
photodamage profile dominated by oxidised purines and sites of base loss (AP sites), whereas 2 mostly induces single-strand
breaks (SSBs) in addition to a small extent of purine oxidative damage. In both cases, DNA oxidative damage would occur
through type I mechanism. In addition, a concerted hydrolytic attack is suggested as an extra mechanism accounting for the
SSBs formation photoinduced by 2. Subcellular internalisation, cyto- and phototoxicity of 1 and 2 and the corresponding
full-aromatic derivatives harmine (3) and harmol (4) also showed quite distinctive patterns in a structure-dependent manner.
These results are discussed in the framework of the potential biological, biomedical and/or pharmacological roles reported
for these alkaloids.},
title = {Photosensitizing properties and subcellular localisation of 3,4‑dihydro‑β‑carbolines harmaline and harmalol},
doi = {10.1007/s43630-022-00328-7},
author = {Denofrio, M. Paula and Paredes Martínez, José Manuel and Yañuk, Juan G. and Girón González, María Dolores and Salto González, Rafael and Talavera Rodríguez, Eva María and Crovetto González, Luis and Cabrerizo, Franco M.},
}