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

Lucas Dias,Mário Calvete,Sara Pinto,Ana Batista De Carvalho,Mariette Pereira,Liane Rossi,M Marques,Gilberto Aquino

doi:10.3390/molecules24010052

Abstract

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.

Highlights

The worldwide burden of cancer is increasing, as it is expected to rise to 22 million cases per year within the two decades
The synthesis of 5,10,15,20-tetrakis(2,6through the covalent linking of β-nitro-metalloporphyrin 5, Scheme 1 to amine functionalized difluorophenyl)porphyrin
The nanomaterial was applied as catalyst in the selective epoxidation of (−)-isopulegol benzyl ether (1), using molecular oxygen as a green oxidant and isobutyraldehyde as co-reductant

Summary

Introduction

The worldwide burden of cancer is increasing, as it is expected to rise to 22 million cases per year within the two decades. The development of new chemical entities that are both non-toxic and active against cancer cells, regarding osteosarcoma, is a high impact challenge. It is well-known that a wide number of compounds isolated from natural products (e.g., essential oils), such as curcumin [2,3,4,5,6], capsaicin [7,8,9,10,11], and terpenes [12,13,14,15,16] have significant in vitro anticancer effects. Monoterpenes, in particular, which are very abundant in plants, display a wide array of biological functions, Molecules 2019, 24, 52; doi:10.3390/molecules24010052 www.mdpi.com/journal/molecules

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