{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,11]],"date-time":"2025-11-11T13:27:51Z","timestamp":1762867671829,"version":"build-2065373602"},"reference-count":65,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2018,12,24]],"date-time":"2018-12-24T00:00:00Z","timestamp":1545609600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["Coimbra Chemistry Centre - PEst-OE\/QUI\/UI0313\/2014","Molecular Physical-Chemistry R&D Unit - UID\/MULTI\/00070\/2013","S.M.A.P - SFRH\/BPD\/84619\/2012","M.J.F.C. - SFRH\/BPD\/99698\/2014"],"award-info":[{"award-number":["Coimbra Chemistry Centre - PEst-OE\/QUI\/UI0313\/2014","Molecular Physical-Chemistry R&D Unit - UID\/MULTI\/00070\/2013","S.M.A.P - SFRH\/BPD\/84619\/2012","M.J.F.C. - SFRH\/BPD\/99698\/2014"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["L.D.D. - PhD grant 232620\/2014-8\/GDE"],"award-info":[{"award-number":["L.D.D. - PhD grant 232620\/2014-8\/GDE"]}],"id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Centro2020","award":["ReNATURE \u2013 CENTRO-01-0145-FEDER-000007"],"award-info":[{"award-number":["ReNATURE \u2013 CENTRO-01-0145-FEDER-000007"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In the present study, we developed a green epoxidation approach for the synthesis of the diastereomers of (\u2212)-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.<\/jats:p>","DOI":"10.3390\/molecules24010052","type":"journal-article","created":{"date-parts":[[2018,12,24]],"date-time":"2018-12-24T10:37:49Z","timestamp":1545647869000},"page":"52","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Bioinspired-Metalloporphyrin Magnetic Nanocomposite as a Reusable Catalyst for Synthesis of Diastereomeric (\u2212)-Isopulegol Epoxide: Anticancer Activity Against Human Osteosarcoma Cells (MG-63)"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2858-7539","authenticated-orcid":false,"given":"Lucas D.","family":"Dias","sequence":"first","affiliation":[{"name":"Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ci\u00eancias e Tecnologia, Universidad de Coimbra, 3004\u2013535 Coimbra, Portugal"},{"name":"Unidade de I&amp;D Qu\u00edmica-F\u00edsica Molecular, Department of Chemistry, University of Coimbra, 3004\u2013535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1280-3321","authenticated-orcid":false,"given":"Ana L. M.","family":"Batista de Carvalho","sequence":"additional","affiliation":[{"name":"Unidade de I&amp;D Qu\u00edmica-F\u00edsica Molecular, Department of Chemistry, University of Coimbra, 3004\u2013535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3817-1182","authenticated-orcid":false,"given":"Sara M. A.","family":"Pinto","sequence":"additional","affiliation":[{"name":"Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ci\u00eancias e Tecnologia, Universidad de Coimbra, 3004\u2013535 Coimbra, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9397-7803","authenticated-orcid":false,"given":"Gilberto L. B.","family":"Aquino","sequence":"additional","affiliation":[{"name":"Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ci\u00eancias e Tecnologia, Universidad de Coimbra, 3004\u2013535 Coimbra, Portugal"},{"name":"Faculty of Pharmacy, State University of Goi\u00e1s, 75132-400 An\u00e1polis, Goias, Brazil"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2094-4781","authenticated-orcid":false,"given":"M\u00e1rio J. F.","family":"Calvete","sequence":"additional","affiliation":[{"name":"Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ci\u00eancias e Tecnologia, Universidad de Coimbra, 3004\u2013535 Coimbra, Portugal"}]},{"given":"Liane M.","family":"Rossi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Fundamental, Instituto de Qu\u00edmica, Universidade de S\u00e3o Paulo, S\u00e3o Paulo 05508\u2013000, Brazil"}]},{"given":"M. P. M.","family":"Marques","sequence":"additional","affiliation":[{"name":"Unidade de I&amp;D Qu\u00edmica-F\u00edsica Molecular, Department of Chemistry, University of Coimbra, 3004\u2013535 Coimbra, Portugal"},{"name":"Department of Life Sciences, University of Coimbra, Cal\u00e7ada Martim de Freitas, 3000\u2013456 Coimbra, Portugal"}]},{"given":"Mariette M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"Coimbra Chemistry Centre, CQC, Departament of Chemistry, Faculdade de Ci\u00eancias e Tecnologia, Universidad de Coimbra, 3004\u2013535 Coimbra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2018,12,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1007\/s40744-016-0046-y","article-title":"Review of Osteosarcoma and Current Management","volume":"3","author":"Durfee","year":"2016","journal-title":"Rheumatol. 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