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Molecules 2018, 23(6), 1382; https://doi.org/10.3390/molecules23061382

Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma

1
Laboratory of Pharmaceutical Chemistry, Universidade Federal da Paraíba, João Pessoa 58051-085, Brazil
2
Department of Molecular Biology and Genetics, Erzurum Technical University, Erzurum 25240, Turkey
3
Programa de Pós-Graduação em Engenharia Química, Universidade Federal de Sergipe, São Cristóvão 49100-000, Brazil
4
Department of Pharmacy, “G. d’Annunzio” University of Chieti-Pescara, Via dei Vestini 31, 66013 Chieti Scalo, CH, Italy
*
Author to whom correspondence should be addressed.
Received: 27 April 2018 / Revised: 14 May 2018 / Accepted: 14 May 2018 / Published: 8 June 2018
(This article belongs to the Special Issue Natural Product Pharmacology and Medicinal Chemistry)
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Abstract

Piplartine (1) is an alkamide extracted from plants of the genus Piper which shows several pharmacological properties, including antitumor activity. To improve this activity, a series of analogues based on 1 have been synthesized by esterification and amidation using the 3,4,5-trimethoxycinnamic acid-like starting material. During the study, the moieties 3-(3,4,5-trimethoxyphenyl)acrylate and 3-(3,4,5-trimethoxyphenyl)acrylamide were maintained on esters and amides respectively. Meanwhile, functional changes were exploited, and it was revealed that the presence of two aromatic rings in the side-chain was important to improve the cytotoxic activity against the U87MG cell line, such as the compound (E)-benzhydryl 3-(3,4,5-trimethoxyphenyl)acrylate (10), an ester that exhibited strong cytotoxicity and a similar level of potency to that of paclitaxel, a positive control. Compound 10 had a marked concentration-dependent inhibitory effect on the viability of the U87MG cell line with apoptotic and oxidative processes, showing good potential for altering main molecular pathways to prevent tumor development. Moreover, it has strong bioavailability with non-genotoxic and non-cytotoxic properties on human blood cells. In conclusion, the findings of the present study demonstrated that compound 10 is a promising agent that may find applications combatting diseases associated with oxidative stress and as a prototype for the development of novel drugs used in the treatment of glioblastoma. View Full-Text
Keywords: cancer; cytotoxic activity; antitumor; phenylpropanoid; alkaloid; natural product; esters; oxidative stress; Piper; synthetic derivatives cancer; cytotoxic activity; antitumor; phenylpropanoid; alkaloid; natural product; esters; oxidative stress; Piper; synthetic derivatives
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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da Nóbrega, F.R.; Ozdemir, O.; Nascimento Sousa, S.C.S.; Barboza, J.N.; Turkez, H.; de Sousa, D.P. Piplartine Analogues and Cytotoxic Evaluation against Glioblastoma. Molecules 2018, 23, 1382.

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