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

仿生金属卟啉磁性纳米复合材料作为可重复使用的催化剂用于合成非对映异构体 (-)-异胡薄荷醇环氧化物:对人类骨肉瘤细胞 (MG-63) 的抗癌活性

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作者: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

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.

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