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Open AccessArticle

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

1
Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ciências e Tecnologia, Universidad de Coimbra, 3004–535 Coimbra, Portugal
2
Unidade de I&D Química-Física Molecular, Department of Chemistry, University of Coimbra, 3004–535 Coimbra, Portugal
3
Faculty of Pharmacy, State University of Goiás, 75132-400 Anápolis, Goias, Brazil
4
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo 05508–000, Brazil
5
Department of Life Sciences, University of Coimbra, Calçada Martim de Freitas, 3000–456 Coimbra, Portugal
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(1), 52; https://doi.org/10.3390/molecules24010052
Received: 22 November 2018 / Revised: 13 December 2018 / Accepted: 18 December 2018 / Published: 24 December 2018
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. View Full-Text
Keywords: hybrid magnetic nanoparticles; manganese(III) porphyrin; epoxidation; molecular oxygen; terpene; isopulegol; anticancer activity; human osteosarcoma hybrid magnetic nanoparticles; manganese(III) porphyrin; epoxidation; molecular oxygen; terpene; isopulegol; anticancer activity; human osteosarcoma
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Dias, L.D.; Batista de Carvalho, A.L.M.; Pinto, S.M.A.; Aquino, G.L.B.; Calvete, M.J.F.; Rossi, L.M.; Marques, M.P.M.; Pereira, M.M. Bioinspired-Metalloporphyrin Magnetic Nanocomposite as a Reusable Catalyst for Synthesis of Diastereomeric (−)-Isopulegol Epoxide: Anticancer Activity Against Human Osteosarcoma Cells (MG-63). Molecules 2019, 24, 52.

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