Bioinspired-Metalloporphyrin Magnetic Nanocomposite as a Reusable Catalyst for Synthesis of Diastereomeric (−)-Isopulegol Epoxide: Anticancer Activity Against Human Osteosarcoma Cells (MG-63)
Lucas D. Dias,
Ana L. M. Batista de Carvalho,
Sara M. A. Pinto,
Gilberto L. B. Aquino,
Mário J. F. Calvete,
Liane M. Rossi,
M. P. M. Marques,
Mariette M. Pereira
Affiliations
Lucas D. Dias
Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004–535 Coimbra, Portugal
Ana L. M. Batista de Carvalho
Unidade de I&D Química-Física Molecular, Department of Chemistry, University of Coimbra, 3004–535 Coimbra, Portugal
Sara M. A. Pinto
Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004–535 Coimbra, Portugal
Gilberto L. B. Aquino
Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004–535 Coimbra, Portugal
Mário J. F. Calvete
Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004–535 Coimbra, Portugal
Liane M. Rossi
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508–000, Brazil
M. P. M. Marques
Unidade de I&D Química-Física Molecular, Department of Chemistry, University of Coimbra, 3004–535 Coimbra, Portugal
Mariette M. Pereira
Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004–535 Coimbra, Portugal
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 IC50 values were significantly lower than those reported for other monoterpene analogues, rendering these epoxide isomers as promising anti-tumor agents against low prognosis osteosarcoma.
