Design and Synthesis of Bis-Chalcones as Curcumin Simplified Analogs and Assessment of Their Antiproliferative Activities Against Human Lung Cancer Cells and <i>Trypanosoma cruzi</i> Amastigotes

<b>Background: </b>Anticancer therapies represent the primary treatment option for a significant number of cancer patients globally; however, many of these treatments are associated with severe side effects as they target molecular structures present in both cancerous and healthy cells....

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Main Authors: Gabriela Alves de Souza, Lorrane de Souza Chaves, Afonso Santine M. M. Velez, Jorge Lucas F. Lacerda, Paulo Pitasse-Santos, Jayane Clys Conceição dos Santos, Otávio Augusto Chaves, Carlos Serpa, Raphael do Carmo Valente, Leonardo Marques da Fonseca, Marcos André Rodrigues da Costa Santos, Jhenifer Santos dos Reis, Carlos Antônio do Nascimento Santos, Lucia Mendonça-Previato, Jose Osvaldo Previato, Celio Geraldo Freire-de-Lima, Debora Decoté-Ricardo, Leonardo Freire-de-Lima, Marco Edilson Freire de Lima
Format: Article
Language:English
Published: MDPI AG 2025-03-01
Series:Pharmaceuticals
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Online Access:https://www.mdpi.com/1424-8247/18/4/456
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Summary:<b>Background: </b>Anticancer therapies represent the primary treatment option for a significant number of cancer patients globally; however, many of these treatments are associated with severe side effects as they target molecular structures present in both cancerous and healthy cells. In a similar context, the treatment of Chagas disease, a neglected tropical illness, is hindered by the high toxicity of the currently available drugs. Researchers are increasingly focusing on the development of safer and more selective alternatives, with natural compounds being studied as potential starting points for the creation of more effective drug candidates with a favorable therapeutic index. <b>Objectives: </b>The aim of this study was to design simplified curcumin-derived structures that preserved or enhanced their therapeutic activity against human lung cancer cell lines and <i>T. cruzi</i>, while also improving bioavailability and minimizing toxicity. <b>Methods: </b>In this study, curcumin and two natural curcuminoids inspired the synthesis of a chalcone and a set of bis-chalcones, compound classes known for their enhanced stability compared with their natural parent derivatives. The synthetic strategy used was the acid-catalyzed aldol condensation reaction. The stability profiles, IC<sub>50</sub> values against A549 and H460 tumor cell lines, and trypanocidal activity against <i>T. cruzi</i> amastigotes of these derivatives were assessed. <b>Results: </b>The synthesized derivatives exhibited improved stability compared with the parent compounds, along with lower IC<sub>50</sub> values in both A549 and H460 tumor cell lines. Additionally, one of the new analogs showed promising trypanocidal activity against <i>T. cruzi</i> amastigotes. <b>Conclusions: </b>This study provides a potential pathway toward the development of more effective and less toxic treatments for both cancer and Chagas disease. The simplified curcumin derivatives represent a promising foundation for designing new therapeutic agents with improved bioavailability and efficacy.
ISSN:1424-8247