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Open AccessArticle

Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy

1
Department of Organic Chemistry, Faculty of Chemical Sciences, Universidad de Concepción, Edmundo Larenas 129, Concepción P.C. 4070371, Chile
2
Institute of Natural Resources Chemistry, Universidad de Talca, Casilla 747, Avenida Lircay, Talca P.C. 3462227, Chile
3
Department of Clinical Biochemistry and Immunology, Faculty of Pharmacy, Universidad de Concepción, Concepción P.C. 4070371, Chile
4
Department of Pharmacology, Faculty of Biological Sciences, Universidad de Concepción, Concepción P.C. 4070371, Chile
*
Authors to whom correspondence should be addressed.
Academic Editor: Yasuyoshi Miyata
Molecules 2020, 25(8), 1911; https://doi.org/10.3390/molecules25081911
Received: 12 March 2020 / Revised: 11 April 2020 / Accepted: 13 April 2020 / Published: 21 April 2020
(This article belongs to the Special Issue Anti-Cancer Drug: Discovery, Development and Combination)
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. View Full-Text
Keywords: cytotoxicity; cancer; Myrtenyl derivatives; multicomponent reactions cytotoxicity; cancer; Myrtenyl derivatives; multicomponent reactions
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MDPI and ACS Style

Concepción, O.; Belmar, J.; F. de la Torre, A.; M. Muñiz, F.; Pertino, M.W.; Alarcón, B.; Ormazabal, V.; Nova-Lamperti, E.; Zúñiga, F.A.; Jiménez, C.A. Synthesis and Cytotoxic Analysis of Novel Myrtenyl Grafted Pseudo-Peptides Revealed Potential Candidates for Anticancer Therapy. Molecules 2020, 25, 1911.

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