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Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy.
Concepción, Odette; Belmar, Julio; F de la Torre, Alexander; M Muñiz, Francisco; Pertino, Mariano W; Alarcón, Barbara; Ormazabal, Valeska; Nova-Lamperti, Estefania; Zúñiga, Felipe A; Jiménez, Claudio A.
Afiliación
  • Concepción O; Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Edmundo Larenas 129, Concepción P.C. 4070371, Chile.
  • Belmar J; Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Edmundo Larenas 129, Concepción P.C. 4070371, Chile.
  • F de la Torre A; Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Edmundo Larenas 129, Concepción P.C. 4070371, Chile.
  • M Muñiz F; Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Edmundo Larenas 129, Concepción P.C. 4070371, Chile.
  • Pertino MW; Institute of Natural Resources Chemistry, Universidad de Talca, Casilla 747, Avenida Lircay, Talca P.C. 3462227, Chile.
  • Alarcón B; Department of Clinical Biochemistry and Immunology, Faculty of Pharmacy, Universidad de Concepción, Concepción P.C. 4070371, Chile.
  • Ormazabal V; Department of Pharmacology, Faculty of Biological Sciences, Universidad de Concepción, Concepción P.C. 4070371, Chile.
  • Nova-Lamperti E; Department of Clinical Biochemistry and Immunology, Faculty of Pharmacy, Universidad de Concepción, Concepción P.C. 4070371, Chile.
  • Zúñiga FA; Department of Clinical Biochemistry and Immunology, Faculty of Pharmacy, Universidad de Concepción, Concepción P.C. 4070371, Chile.
  • Jiménez CA; Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Edmundo Larenas 129, Concepción P.C. 4070371, Chile.
Molecules ; 25(8)2020 Apr 21.
Article en En | MEDLINE | ID: mdl-32326138
Myrtenal is a natural monoterpene isolated from essential oils of several plants and their derivates have shown to have several biological properties including cytotoxicity. The cytotoxic activity of these derivates are being investigated for their antitumor effect leading to the development of potential anticancer agents. In this study, novels Myrtenyl grafted pseudo-peptides were designed, synthesized and functionally characterized as possible therapeutic agents for cancer treatment. Thirteen novel Myrtenyl grafted pseudo-peptides were prepared in high atom economy and efficiency by a classic Ugi-4CR and sequential post-modification. Their structures were confirmed by NMR, and ESI-MS, and its cytotoxic activity was evaluated in three cancer cell lines and primary CD4+ T cells at different proliferative cycles. Our results revealed that some of these compounds showed significant cytotoxicity against human gastric, breast and colon adenocarcinoma cells lines, but not against human dermal fibroblast cell line. Moreover, from the thirteen novel myrtenyl synthesized the compound (1R,5S)-N-{[1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-N-[2-(cyclohexylamino)-2-oxoethyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxamide (3b) proved to be the best candidate in terms of acceptable EC50, and Emax values in cancer cell lines and at inducing cytotoxicity in CD4+ T cells undergoing active proliferation, without affecting non-proliferating T cells. Overall, the synthesis and characterization of our Myrtenyl derivates revealed novel potential anticancer candidates with selective cytotoxic activity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos / Técnicas de Química Sintética / Antineoplásicos Límite: Humans Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2020 Tipo del documento: Article País de afiliación: Chile Pais de publicación: Suiza
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos / Técnicas de Química Sintética / Antineoplásicos Límite: Humans Idioma: En Revista: Molecules Asunto de la revista: BIOLOGIA Año: 2020 Tipo del documento: Article País de afiliación: Chile Pais de publicación: Suiza