Exploring the Anticancer Properties of 1,2,3-Triazole-Substituted Andrographolide Derivatives

<b>Background/Objectives</b>: The search for new anticancer agents from natural sources remains a key strategy in drug discovery. This study aimed to synthesize and evaluate novel triazole derivatives of the diterpenic lactone andrographolide for their antiproliferative activity against...

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Main Authors: Joana R. L. Ribeiro, Juliana Calheiros, Rita A. M. Silva, Bruno M. F. Gonçalves, Carlos A. M. Afonso, Lucília Saraiva, Maria-José U. Ferreira
Format: Article
Language:English
Published: MDPI AG 2025-05-01
Series:Pharmaceuticals
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Online Access:https://www.mdpi.com/1424-8247/18/5/750
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Summary:<b>Background/Objectives</b>: The search for new anticancer agents from natural sources remains a key strategy in drug discovery. This study aimed to synthesize and evaluate novel triazole derivatives of the diterpenic lactone andrographolide for their antiproliferative activity against various cancer cell lines. <b>Methods</b>: Twenty-two new triazole derivatives (<b>5</b>–<b>26</b>), of the triacetyl derivative (<b>2</b>) of the diterpenic lactone andrographolide (<b>1</b>), were synthesized via the azide-alkyne “click reaction”. The antiproliferative effects of compounds <b>1</b>–<b>26</b> were evaluated using the sulforhodamine B assay against a panel of cancer cell lines and a non-tumorigenic colon cell line. A representative compound, triazole derivative <b>12</b>, was further evaluated in human pancreatic ductal adenocarcinoma (PANC-1) cells for its effects on the cell cycle, apoptosis, migration, and drug synergy with 5-fluorouracil. <b>Results</b>: Several compounds, specifically, <b>9</b>, <b>14</b>, <b>16,</b> and <b>17</b>, bearing a phenyl moiety, exhibited improved antiproliferative activity compared to the parental compound <b>1</b>. Derivative <b>12</b>, selected for further investigation, induced G2/M cell cycle arrest and apoptosis in a concentration-dependent manner. Additionally, this compound significantly reduced cell migration and demonstrated synergistic effects with 5-fluorouracil in PANC-1 cells. <b>Conclusions</b>: The synthesized andrographolide-based triazole derivatives, particularly compound <b>12</b>, showed promising antiproliferative activity and mechanisms relevant to cancer therapy. These findings support their potential as lead compounds for further development in anticancer research.
ISSN:1424-8247