RT Journal Article
T1 Synthesis, solubility and antitumor activity of maslinic acid derivatives.
A1 Fuentes-Ríos, David
A1 Cepero, Ana
A1 García-Castro, Miguel
A1 Contreras-Cáceres, Rafael
A1 López-Romero, Juan Manuel
A1 Luque, Cristina
A1 Cabeza, Laura
A1 Melguizo, Consolación
A1 Prados, José
K1 Triterpenos
K1 Enlaces químicos
K1 Neurotransmisores
K1 Cáncer
K1 Citotoxicidad por mediación celular
AB Maslinic acid (MA), a pentacyclic triterpenoid obtained from olives that is characterized by its antiproliferativeactivity in tumor cells, has become a promising molecule that could be modi ed to improve cancer treatment. Inthis work we have synthesized in good yields several new MA conjugates, including glycerin, oligo(ethyleneglycol), and amino acid derivatives (compounds 3a-f). The synthesis offers the possibility of recovering unreactedMA, and thus the scaling up of the process. For the tyramine-MA conjugate, compound 3f or TMA, the preparationhas been optimized to a one-pot reaction. Solubility of conjugates in polar solvents has been measured, showing amarked increase of solubility with respect to MA. Moreover, we selected the tyramidyl maslinic acid conjugate (3for TMA) to determine antitumor capacity over a wide range of cancer cell lines, including glioblastoma, mela-noma, breast, lung, colorectal and pancreatic cancer. Our results clearly demonstrated that TMA induced highercytotoxicity in all cancer cell types compared to MA. TMA was more effective than MA, especially in breast cancercells (MCF-7) and melanoma cells (B16–F10) where IC50 reductions of 4.12 and 4.72, respectively, was detected.Interestingly, TMA showed a remarkable antitumor ability against the resistant HCT-15 colon cancer cell line.Furthermore, we demonstrated for the rst time a relevant effect of a MA derivative against glioblastoma cells(A172 and SF-268). These results suggest that TMA is able to improve the antitumor characteristics of MA in awide range of cancers and that it may be a promising compound for various tumor types, including resistantcancer.
PB Elsevier
YR 2022
FD 2022-02-05
LK https://hdl.handle.net/10630/40476
UL https://hdl.handle.net/10630/40476
LA eng
NO European Journal of Medicinal Chemistry Reports 4 (2022) 100032
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 20 ene 2026