Synthesis, characterization, theoretical studies and biological (antioxidant, anticancer, toxicity and neuroprotective) determinations of a copper(II) complex with 5-hydroxytryptophan.

Autor: Martínez Medina JJ; Universidad Nacional del Chaco Austral, Comandante Fernández, 755 - CP: 3700, Presidencia Roque Sáenz Peña, Chaco, Argentina., Naso LG; CEQUINOR, CONICET/CICPBA/UNLP, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 Nº 1465, 1900 La Plata, Argentina., Pérez AL; Departamento de Física, Facultad de Bioquímica y Ciencias Biológicas, Universidad Nacional del Litoral, Ciudad Universitaria-Paraje El Pozo, 3000 Santa Fe, Argentina., Rizzi A; Departamento de Física, Facultad de Bioquímica y Ciencias Biológicas, Universidad Nacional del Litoral, Ciudad Universitaria-Paraje El Pozo, 3000 Santa Fe, Argentina., Okulik NB; Universidad Nacional del Chaco Austral, Comandante Fernández, 755 - CP: 3700, Presidencia Roque Sáenz Peña, Chaco, Argentina., Valcarcel M; Innoprot SL, Edificio 502-P1- Parque Tecnológico, 48160, Derio, Spain., Salado C; Innoprot SL, Edificio 502-P1- Parque Tecnológico, 48160, Derio, Spain., Ferrer EG; CEQUINOR, CONICET/CICPBA/UNLP, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 Nº 1465, 1900 La Plata, Argentina., Williams PAM; CEQUINOR, CONICET/CICPBA/UNLP, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 Nº 1465, 1900 La Plata, Argentina. Electronic address: williams@quimica.unlp.edu.ar.
Jazyk: angličtina
Zdroj: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie [Biomed Pharmacother] 2019 Mar; Vol. 111, pp. 414-426. Date of Electronic Publication: 2018 Dec 27.
DOI: 10.1016/j.biopha.2018.12.098
Abstrakt: 5-Hydroxy-L-tryptophan (5-HTP) is a serotonin pathway metabolite of L-tryptophan in the brain. In the knowledge that the biological properties of some compounds can be modified upon metal complexation, a new solid metal complex, [Cu(5-hydroxytryptophan) 2 ].H 2 O (Cu5HTP), has been synthesized and characterized to analyze the modification of some biological properties. The conformational investigations (optimized in gas phase at B3LYP/6-311G** theory level) suggest the coexistence of two conformers of Cu5HTP with cis- and trans- arrangements of the amino acids in the equatorial plane. The trans- Cu5HTP1 complex is the most stable conformer. The complexation led to an enhancement of the antioxidant properties of the ligand. The metal complex also improved the anticancer behavior of the ligand (tested in cancer cell lines derived from human lung (A549), cervix (HeLa) and colon (HCT-116)). It did not show toxicity against either the non-malignant human lung fibroblast (MRC-5) cell line or Artemia salina and did not behave as mutagenic agent (Ames test). Cellular reactive oxygen species production may be one of the possible mechanisms of action. Besides, the metal complex exerted neuroprotective action on cortical neurons from embryonic 18 days rats exposed to glutamate.
(Copyright © 2018 Elsevier Masson SAS. All rights reserved.)
Databáze: MEDLINE
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