Novel 4-Aryl-4H-chromene derivative displayed excellent in vivo anti-glioblastoma efficacy as the microtubule-targeting agent
In this study, a series of novel 4-Aryl-4H-chromene derivatives (D1-D31) were designed and synthesized by integrating quinoline heterocycle to crolibulin template molecule based on the strategy of molecular hybridization. One of these compounds D19 displayed positive antiproliferative activity again...
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| Published in | European journal of medicinal chemistry Vol. 267; p. 116205 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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ISSY-LES-MOULINEAUX
Elsevier Masson SAS
05.03.2024
Elsevier |
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| Abstract | In this study, a series of novel 4-Aryl-4H-chromene derivatives (D1-D31) were designed and synthesized by integrating quinoline heterocycle to crolibulin template molecule based on the strategy of molecular hybridization. One of these compounds D19 displayed positive antiproliferative activity against U87 cancer cell line (IC50 = 0.90 ± 0.03 μM). Compound D19 was verified as the microtubule-targeting agent through downregulating tubulin related genes of U87 cells, destroying the cytoskeleton of tubulins and interacting with the colchicine-binding site to inhibit the polymerization of tubulins by transcriptome analysis, immune-fluorescence staining, microtubule dynamics and EBI competition assays as well as molecular docking simulations. Moreover, compound D19 induced G2/M phase arrest, resulted in cell apoptosis and inhibited the migration of U87 cells by flow cytometry analysis and wound healing assays. Significantly, compound D19 dose-dependently inhibited the tumor growth of orthotopic glioma xenografts model (GL261-Luc) and effectively prolonged the survival time of mice, which were extremely better than those of positive drug temozolomide (TMZ). Compound D19 exhibited potent in vivo antivascular activity as well as no observable toxicity. Furthermore, the results of in silico simulation studies and P-gp transwell assays verified the positive correlation between compound D19's Blood-Brain Barrier (BBB) permeability and its in vivo anti-GBM activity. Overall, compound D19 can be used as a promising anti-GBM lead compound for the treatment of glioblastoma.
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•Thirty-one 4-Aryl-4H-chromene derivatives were synthesized and investigated.•The compound D19 acted as the microtubule-targeting agent.•The compound D19 displayed excellent anti-glioblastoma activity in vivo. |
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| AbstractList | In this study, a series of novel 4-Aryl-4H-chromene derivatives (D1-D31) were designed and synthesized by integrating quinoline heterocycle to crolibulin template molecule based on the strategy of molecular hybridization. One of these compounds D19 displayed positive antiproliferative activity against U87 cancer cell line (IC50 = 0.90 ± 0.03 μM). Compound D19 was verified as the microtubule-targeting agent through downregulating tubulin related genes of U87 cells, destroying the cytoskeleton of tubulins and interacting with the colchicine-binding site to inhibit the polymerization of tubulins by transcriptome analysis, immune-fluorescence staining, microtubule dynamics and EBI competition assays as well as molecular docking simulations. Moreover, compound D19 induced G2/M phase arrest, resulted in cell apoptosis and inhibited the migration of U87 cells by flow cytometry analysis and wound healing assays. Significantly, compound D19 dose-dependently inhibited the tumor growth of orthotopic glioma xenografts model (GL261-Luc) and effectively prolonged the survival time of mice, which were extremely better than those of positive drug temozolomide (TMZ). Compound D19 exhibited potent in vivo antivascular activity as well as no observable toxicity. Furthermore, the results of in silico simulation studies and P-gp transwell assays verified the positive correlation between compound D19's Blood-Brain Barrier (BBB) permeability and its in vivo anti-GBM activity. Overall, compound D19 can be used as a promising anti-GBM lead compound for the treatment of glioblastoma.
[Display omitted]
•Thirty-one 4-Aryl-4H-chromene derivatives were synthesized and investigated.•The compound D19 acted as the microtubule-targeting agent.•The compound D19 displayed excellent anti-glioblastoma activity in vivo. In this study, a series of novel 4-Aryl-4H-chromene derivatives (D1-D31) were designed and synthesized by integrating quinoline heterocycle to crolibulin template molecule based on the strategy of molecular hybridization. One of these compounds D19 displayed positive antiproliferative activity against U87 cancer cell line (IC = 0.90 ± 0.03 μM). Compound D19 was verified as the microtubule-targeting agent through downregulating tubulin related genes of U87 cells, destroying the cytoskeleton of tubulins and interacting with the colchicine-binding site to inhibit the polymerization of tubulins by transcriptome analysis, immune-fluorescence staining, microtubule dynamics and EBI competition assays as well as molecular docking simulations. Moreover, compound D19 induced G2/M phase arrest, resulted in cell apoptosis and inhibited the migration of U87 cells by flow cytometry analysis and wound healing assays. Significantly, compound D19 dose-dependently inhibited the tumor growth of orthotopic glioma xenografts model (GL261-Luc) and effectively prolonged the survival time of mice, which were extremely better than those of positive drug temozolomide (TMZ). Compound D19 exhibited potent in vivo antivascular activity as well as no observable toxicity. Furthermore, the results of in silico simulation studies and P-gp transwell assays verified the positive correlation between compound D19's Blood-Brain Barrier (BBB) permeability and its in vivo anti-GBM activity. Overall, compound D19 can be used as a promising anti-GBM lead compound for the treatment of glioblastoma. In this study, a series of novel 4-Aryl-4H-chromene derivatives (D1-D31) were designed and synthesized by integrating quinoline heterocycle to crolibulin template molecule based on the strategy of molecular hybridization. One of these compounds D19 displayed positive antiproliferative activity against U87 cancer cell line (IC50 = 0.90 +/- 0.03 mu M). Compound D19 was verified as the microtubule-targeting agent through downregulating tubulin related genes of U87 cells, destroying the cytoskeleton of tubulins and interacting with the colchicine-binding site to inhibit the polymerization of tubulins by transcriptome analysis, immune-fluorescence staining, microtubule dynamics and EBI competition assays as well as molecular docking simulations. Moreover, compound D19 induced G2/M phase arrest, resulted in cell apoptosis and inhibited the migration of U87 cells by flow cytometry analysis and wound healing assays. Significantly, compound D19 dose-dependently inhibited the tumor growth of orthotopic glioma xenografts model (GL261-Luc) and effectively prolonged the survival time of mice, which were extremely better than those of positive drug temozolomide (TMZ). Compound D19 exhibited potent in vivo antivascular activity as well as no observable toxicity. Furthermore, the results of in silico simulation studies and P-gp transwell assays verified the positive correlation between compound D19's Blood-Brain Barrier (BBB) permeability and its in vivo anti-GBM activity. Overall, compound D19 can be used as a promising anti-GBM lead compound for the treatment of glioblastoma. In this study, a series of novel 4-Aryl-4H-chromene derivatives (D1-D31) were designed and synthesized by integrating quinoline heterocycle to crolibulin template molecule based on the strategy of molecular hybridization. One of these compounds D19 displayed positive antiproliferative activity against U87 cancer cell line (IC50 = 0.90 ± 0.03 μM). Compound D19 was verified as the microtubule-targeting agent through downregulating tubulin related genes of U87 cells, destroying the cytoskeleton of tubulins and interacting with the colchicine-binding site to inhibit the polymerization of tubulins by transcriptome analysis, immune-fluorescence staining, microtubule dynamics and EBI competition assays as well as molecular docking simulations. Moreover, compound D19 induced G2/M phase arrest, resulted in cell apoptosis and inhibited the migration of U87 cells by flow cytometry analysis and wound healing assays. Significantly, compound D19 dose-dependently inhibited the tumor growth of orthotopic glioma xenografts model (GL261-Luc) and effectively prolonged the survival time of mice, which were extremely better than those of positive drug temozolomide (TMZ). Compound D19 exhibited potent in vivo antivascular activity as well as no observable toxicity. Furthermore, the results of in silico simulation studies and P-gp transwell assays verified the positive correlation between compound D19's Blood-Brain Barrier (BBB) permeability and its in vivo anti-GBM activity. Overall, compound D19 can be used as a promising anti-GBM lead compound for the treatment of glioblastoma. |
| ArticleNumber | 116205 |
| Author | Lu, Yuanyuan Jiang, Feng Cao, Feng Yang, Haoyi Qiao, Haishi Zhang, Dongyu Yuan, Ziyang Xia, Zhuolu |
| Author_xml | – sequence: 1 givenname: Haoyi surname: Yang fullname: Yang, Haoyi organization: School of Life Science and Technology, China Pharmaceutical University, Nanjing, 210009, China – sequence: 2 givenname: Dongyu surname: Zhang fullname: Zhang, Dongyu organization: School of Engineering, China Pharmaceutical University, Nanjing, 210009, China – sequence: 3 givenname: Ziyang surname: Yuan fullname: Yuan, Ziyang organization: School of Engineering, China Pharmaceutical University, Nanjing, 210009, China – sequence: 4 givenname: Haishi surname: Qiao fullname: Qiao, Haishi organization: School of Engineering, China Pharmaceutical University, Nanjing, 210009, China – sequence: 5 givenname: Zhuolu surname: Xia fullname: Xia, Zhuolu organization: School of Engineering, China Pharmaceutical University, Nanjing, 210009, China – sequence: 6 givenname: Feng orcidid: 0009-0009-2363-9871 surname: Cao fullname: Cao, Feng email: cpufengc@cpu.edu.cn organization: School of Pharmacy, China Pharmaceutical University, Nanjing, 210009, China – sequence: 7 givenname: Yuanyuan orcidid: 0000-0001-8327-5146 surname: Lu fullname: Lu, Yuanyuan email: luyy@cpu.edu.cn organization: School of Life Science and Technology, China Pharmaceutical University, Nanjing, 210009, China – sequence: 8 givenname: Feng orcidid: 0000-0001-9633-6884 surname: Jiang fullname: Jiang, Feng email: jiangfeng@cpu.edu.cn organization: School of Engineering, China Pharmaceutical University, Nanjing, 210009, China |
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| Keywords | Anti-glioblastoma 4-Aryl-4H-chromene Microtubule-targeting agent BBB permeability DESIGN DISCOVERY STRATEGIES MOLECULES DISRUPTION BIOLOGICAL EVALUATION CHEMISTRY INHIBITORS TUBULIN SCAFFOLD |
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| SubjectTerms | 4-Aryl-4H-chromene Animals Anti-glioblastoma Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antineoplastic Agents - therapeutic use BBB permeability Benzopyrans - pharmacology Benzopyrans - therapeutic use Cell Line, Tumor Cell Proliferation Chemistry, Medicinal Drug Screening Assays, Antitumor Glioblastoma - drug therapy Humans Life Sciences & Biomedicine Mice Microtubule-targeting agent Microtubules - metabolism Molecular Docking Simulation Pharmacology & Pharmacy Science & Technology Structure-Activity Relationship Tubulin - metabolism Tubulin Modulators - pharmacology |
| Title | Novel 4-Aryl-4H-chromene derivative displayed excellent in vivo anti-glioblastoma efficacy as the microtubule-targeting agent |
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