RT Journal Article
T1 Synthesis, Optical Properties, and Antiproliferative Evaluation of NBD-Triterpene Fluorescent Probes.
A1 Medina O´Donnell, Marta
A1 Vega Granados, Karina
A1 Martinez, Antonio
A1 Sepúlveda, M. Rosario
A1 Molina-Bolívar, José Antonio
A1 Álvarez de Cienfuegos, Luis
A1 Parra, Andrés
A1 Reyes Zurita, Fernando
A1 Rivas, Francisco
K1 Compuestos orgánicos
K1 Fluorescencia
K1 Terpenos
AB A fluorescent labeling protocol for hydroxylated natural compounds with promising antitumor properties has been used tosynthesize, in yields of 72−86%, 12 derivatives having fluorescent properties and biological activity. The reagent used for the synthesis of these fluorescent derivatives was 7-nitrobenzo-2-oxa-1,3-diazole chloride (NBD-Cl). The linkers employed to bind the NBD-Cl reagent to the natural compounds were ω-amino acids (Aa) of different chain lengths. The natural triterpene compounds chosen were oleanolic and maslinic acid, as their corresponding 28-benzylated derivatives. Thus, 12 NBDAa-triterpene conjugates have been studied for their optical fluorescence properties and their biological activities against cell proliferation in three cancer cell lines (B16-F10, HT-29, and HepG2), compared with three nontumor cell lines (HPF, IEC-18, and WRL68) from different tissues. The results of the fluorescence study have shown that the best fluorescent labels are those in which the ω-amino acid chain is shorter, and the carboxylic group is not benzylated. Analysis by confocal microscopy showed that these compounds were rapidly incorporated into cells in all three cancer cell lines, with these same derivatives showing the highest toxicity against the cancer cell lines tested. Then, the fluorescent labeling of these NBD-Aa-triterpene conjugates enabled their uptake and subcellular distribution to be followed in order to probe in detail their biological properties at the cellular and molecular level.
YR 2022
FD 2022-12-21
LK https://hdl.handle.net/10630/35458
UL https://hdl.handle.net/10630/35458
LA eng
NO ACS
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 26 ene 2026