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Abstract <p><b>Objective:</b> Indole, a nitrogen-containing heterocyclic compound, exhibits a range of pharmacological effects, including antimicrobial, anti-inflammatory, and anticancer properties. Colorectal cancer is a leading cause of cancer-related mortality worldwide. This study aimed to evaluate the antitumor activity of a newly synthesized indole derivative, 2-((2-chloro-5-nitrophenyl)(1<i>H</i>-indol-3-yl)methyl)-2<i>H</i>-indene-1,3-dione (designated as 2Cl-5<i>N</i>-ind-dione), on HT-29 colorectal adenocarcinoma cells. <b>Methods:</b> The novel compound 2Cl-5<i>N</i>-ind-dione was synthesized and its structure was confirmed by <sup>1</sup>H, <sup>13</sup>C NMR, and FT-IR spectroscopy. Its antitumor efficacy was assessed using the MTT assay, Annexin V/PI staining, and quantitative RT-PCR. <b>Results and Discussion:</b> Treatment with compound 2Cl-5<i>N</i>-ind-dione exerted cytotoxic effects on HT-29 cells with IC<sub>50</sub> values of 70.54, 23.64, and 22.18 µg/mL at 24, 48, and 72 h, respectively. The compound modulated the expression of specific microRNAs: it upregulated the tumor-suppressive miRNAs miR-200a and miR-34a, while downregulating miR-181a. Wound healing assays, flow cytometry, and qRT-PCR analysis confirmed that 2Cl-5<i>N</i>-ind-dione inhibited cell migration and induced apoptosis in HT-29 cells compared to untreated controls. <b>Conclusions:</b> Our data indicate that compound 2Cl-5<i>N</i>-ind-dione acts as an anti-proliferative, antimigratory, and pro-apoptotic agent. These effects are likely mediated by the observed modulation of miR-200a, miR-34a, and miR-181a, which are known to target key pathways involved in apoptosis and cell migration.</p>

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Design and Synthesis of a Novel Indole Derivative (2Cl-5N-ind-dione) and its Effect on miR-181a, miR-200a, and miR-34a Expression, Targeting Apoptosis, and Migration Pathways in HT-29 Colorectal Cancer Cells

  • 期刊论文

  • 发表日期：

    2025年12月1日

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  • M. Rasaei,
  • E. Mohajeri,
  • A. Sahranavard Siahmazgi,
  • S. Nezamivand Chegini,
  • S. Dabirian,
  • H. Zahmatkesh,
  • H. S. Kamalifar,
  • B. Rasti,
  • M. Shahriarinour,
  • N. Ranji,
  • M. Nikpassand

摘要

Abstract

Objective: Indole, a nitrogen-containing heterocyclic compound, exhibits a range of pharmacological effects, including antimicrobial, anti-inflammatory, and anticancer properties. Colorectal cancer is a leading cause of cancer-related mortality worldwide. This study aimed to evaluate the antitumor activity of a newly synthesized indole derivative, 2-((2-chloro-5-nitrophenyl)(1H-indol-3-yl)methyl)-2H-indene-1,3-dione (designated as 2Cl-5N-ind-dione), on HT-29 colorectal adenocarcinoma cells. Methods: The novel compound 2Cl-5N-ind-dione was synthesized and its structure was confirmed by 1H, 13C NMR, and FT-IR spectroscopy. Its antitumor efficacy was assessed using the MTT assay, Annexin V/PI staining, and quantitative RT-PCR. Results and Discussion: Treatment with compound 2Cl-5N-ind-dione exerted cytotoxic effects on HT-29 cells with IC50 values of 70.54, 23.64, and 22.18 µg/mL at 24, 48, and 72 h, respectively. The compound modulated the expression of specific microRNAs: it upregulated the tumor-suppressive miRNAs miR-200a and miR-34a, while downregulating miR-181a. Wound healing assays, flow cytometry, and qRT-PCR analysis confirmed that 2Cl-5N-ind-dione inhibited cell migration and induced apoptosis in HT-29 cells compared to untreated controls. Conclusions: Our data indicate that compound 2Cl-5N-ind-dione acts as an anti-proliferative, antimigratory, and pro-apoptotic agent. These effects are likely mediated by the observed modulation of miR-200a, miR-34a, and miR-181a, which are known to target key pathways involved in apoptosis and cell migration.