Bioinspired-Metalloporphyrin Magnetic Nanocomposite as a Reusable Catalyst for Synthesis of Diastereomeric (-)-Isopulegol Epoxide: Anticancer Activity Against Human Osteosarcoma Cells (MG-63).

Autor: Dias LD; Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004⁻535 Coimbra, Portugal. lucasdanillodias@gmail.com.; Unidade de I&D Química-Física Molecular, Department of Chemistry, University of Coimbra, 3004⁻535 Coimbra, Portugal. lucasdanillodias@gmail.com., Batista de Carvalho ALM; Unidade de I&D Química-Física Molecular, Department of Chemistry, University of Coimbra, 3004⁻535 Coimbra, Portugal. almbc@ci.uc.pt., Pinto SMA; Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004⁻535 Coimbra, Portugal. smpinto@qui.uc.pt., Aquino GLB; Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004⁻535 Coimbra, Portugal. gilberto.benedito@ueg.br.; Faculty of Pharmacy, State University of Goiás, 75132-400 Anápolis, Goias, Brazil. gilberto.benedito@ueg.br., Calvete MJF; Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004⁻535 Coimbra, Portugal. mcalvete@qui.uc.pt., Rossi LM; Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508⁻000, Brazil. lrossi@iq.usp.br., Marques MPM; Unidade de I&D Química-Física Molecular, Department of Chemistry, University of Coimbra, 3004⁻535 Coimbra, Portugal. pmc@ci.uc.pt.; Department of Life Sciences, University of Coimbra, Calçada Martim de Freitas, 3000⁻456 Coimbra, Portugal. pmc@ci.uc.pt., Pereira MM; Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004⁻535 Coimbra, Portugal. mmpereira@qui.uc.pt.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2018 Dec 24; Vol. 24 (1). Date of Electronic Publication: 2018 Dec 24.
DOI: 10.3390/molecules24010052
Abstrakt: In the present study, we developed a green epoxidation approach for the synthesis of the diastereomers of (-)-isopulegol benzyl ether epoxide using molecular oxygen as the oxidant and a hybrid manganese(III)-porphyrin magnetic reusable nanocomposite as the catalyst. High activity, selectivity, and stability were obtained, with up to four recycling cycles without the loss of activity and selectivity for epoxide. The anticancer effect of the newly synthesized isopulegol epoxide diastereomers was evaluated on a human osteosarcoma cell line (MG-63); both diastereomers showed similar in vitro potency. The measured IC 50 values were significantly lower than those reported for other monoterpene analogues, rendering these epoxide isomers as promising anti-tumor agents against low prognosis osteosarcoma.
Databáze: MEDLINE
Externí odkaz: