Design, Synthesis and Radioprotective Activity Evaluation of Novel N-Phenyl-2H-chromene-3-carboxamides Derived from Ex-RAD
Exposures to ionizing radiation can cause serious damages to human body, and the development of radiation countermeasures is urgently needed. In this paper, a series of N-phenyl-2H-chromene-3-carboxamides were designed and synthesized as potential radiation countermeasures. Their radioprotective act...
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| Published in | Chemical & pharmaceutical bulletin Vol. 73; no. 7; pp. 600 - 615 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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The Pharmaceutical Society of Japan
10.07.2025
Japan Science and Technology Agency |
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| Abstract | Exposures to ionizing radiation can cause serious damages to human body, and the development of radiation countermeasures is urgently needed. In this paper, a series of N-phenyl-2H-chromene-3-carboxamides were designed and synthesized as potential radiation countermeasures. Their radioprotective activities were evaluated in vitro and in vivo, and compound B5 was identified as the most effective molecule among the target compounds. B5 can not only accelerate the recovery of peripheral blood cells in mice exposed to total body irradiation, but also alleviate damage to the small intestine, spleen and thymus in mice exposed to abdominal irradiation. Furthermore, B5 exhibited superior ability to mitigate radiation-induced DNA damage and apoptosis in irradiated AHH-1 cells. Western blot analysis indicated that the radioprotection provided by B5 resulted in the downregulation of pro-apoptosis proteins p53 and upregulation of anti-apoptosis protein Bcl-2. In addition, the RNA-Sequencing analysis revealed that B5 primarily exerts its radioprotective effects through the Wnt signaling pathway and the mitogen-activated protein kinase (MAPK) signaling pathway. In conclusion, we identified B5 as a promising radioprotective compound, and B5 is valuable for further research in the future. |
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| AbstractList | Exposures to ionizing radiation can cause serious damages to human body, and the development of radiation countermeasures is urgently needed. In this paper, a series of N-phenyl-2H-chromene-3-carboxamides were designed and synthesized as potential radiation countermeasures. Their radioprotective activities were evaluated in vitro and in vivo, and compound B5 was identified as the most effective molecule among the target compounds. B5 can not only accelerate the recovery of peripheral blood cells in mice exposed to total body irradiation, but also alleviate damage to the small intestine, spleen and thymus in mice exposed to abdominal irradiation. Furthermore, B5 exhibited superior ability to mitigate radiation-induced DNA damage and apoptosis in irradiated AHH-1 cells. Western blot analysis indicated that the radioprotection provided by B5 resulted in the downregulation of pro-apoptosis proteins p53 and upregulation of anti-apoptosis protein Bcl-2. In addition, the RNA-Sequencing analysis revealed that B5 primarily exerts its radioprotective effects through the Wnt signaling pathway and the mitogen-activated protein kinase (MAPK) signaling pathway. In conclusion, we identified B5 as a promising radioprotective compound, and B5 is valuable for further research in the future. Exposures to ionizing radiation can cause serious damages to human body, and the development of radiation countermeasures is urgently needed. In this paper, a series of N-phenyl-2H-chromene-3-carboxamides were designed and synthesized as potential radiation countermeasures. Their radioprotective activities were evaluated in vitro and in vivo, and compound B5 was identified as the most effective molecule among the target compounds. B5 can not only accelerate the recovery of peripheral blood cells in mice exposed to total body irradiation, but also alleviate damage to the small intestine, spleen and thymus in mice exposed to abdominal irradiation. Furthermore, B5 exhibited superior ability to mitigate radiation-induced DNA damage and apoptosis in irradiated AHH-1 cells. Western blot analysis indicated that the radioprotection provided by B5 resulted in the downregulation of pro-apoptosis proteins p53 and upregulation of anti-apoptosis protein Bcl-2. In addition, the RNA-Sequencing analysis revealed that B5 primarily exerts its radioprotective effects through the Wnt signaling pathway and the mitogen-activated protein kinase (MAPK) signaling pathway. In conclusion, we identified B5 as a promising radioprotective compound, and B5 is valuable for further research in the future.Exposures to ionizing radiation can cause serious damages to human body, and the development of radiation countermeasures is urgently needed. In this paper, a series of N-phenyl-2H-chromene-3-carboxamides were designed and synthesized as potential radiation countermeasures. Their radioprotective activities were evaluated in vitro and in vivo, and compound B5 was identified as the most effective molecule among the target compounds. B5 can not only accelerate the recovery of peripheral blood cells in mice exposed to total body irradiation, but also alleviate damage to the small intestine, spleen and thymus in mice exposed to abdominal irradiation. Furthermore, B5 exhibited superior ability to mitigate radiation-induced DNA damage and apoptosis in irradiated AHH-1 cells. Western blot analysis indicated that the radioprotection provided by B5 resulted in the downregulation of pro-apoptosis proteins p53 and upregulation of anti-apoptosis protein Bcl-2. In addition, the RNA-Sequencing analysis revealed that B5 primarily exerts its radioprotective effects through the Wnt signaling pathway and the mitogen-activated protein kinase (MAPK) signaling pathway. In conclusion, we identified B5 as a promising radioprotective compound, and B5 is valuable for further research in the future. |
| ArticleNumber | c25-00105 |
| Author | Liu, Xiao-Han Xu, Jing Liu, Xin-Ru Feng, Han-Yin Peng, Tao Liu, Shu-Chen Zhang, Shou-Guo |
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| Cites_doi | 10.1016/j.heliyon.2024.e32010 10.1016/j.mrrev.2013.02.001 10.1016/j.molstruc.2024.138149 10.3390/ijms25136973 10.3389/fphar.2021.643283 10.1016/j.biopha.2018.06.150 10.1016/j.ejmech.2024.116239 10.1016/j.jviscsurg.2020.08.012 10.3892/mmr.2023.12953 10.1016/j.micron.2017.02.004 10.1039/C7MD00573C 10.1080/09553002.2020.1820598 10.1007/s13277-010-0042-8 10.1016/j.ejmech.2024.116346 10.1016/j.bioorg.2021.104714 10.1358/dot.2022.58.3.3367994 10.1097/HP.0000000000001385 10.1021/acs.jmedchem.0c00530 10.1088/1361-6498/ac20e0 10.1667/RR1367.1 10.1007/s11356-020-09618-y 10.1039/C7MD00017K 10.1038/sj.cdd.4401231 10.1093/jrr/rrs001 10.3892/or.2017.5940 10.1016/j.ejmech.2024.116121 10.1016/j.tracli.2024.07.002 10.1371/journal.pone.0058355 |
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Res., 753, 24–40 (2013). – reference: 7) Hollingsworth B., Cassatt D., DiCarlo A., Rios C., Satyamitra M., Winters T., Taliaferro L., Front. Pharmacol., 12, 643283 (2021). – reference: 4) Pariset E., Malkani S., Cekanaviciute E., Costes S., Int. J. Radiat. Biol., 97 (supp1.), S132–S150 (2021). – reference: 21) Bandaru V., Juvale K., Reddy Anugu S., Vishwakarma S., Kumar A., Doddipalla R., Sunanda K. S., Jadhav V., Vidavalur S., J. Mol. Struct., 1309, 138149 (2024). – reference: 11) Mishra K. N., Moftah B. A., Alsbeih G. A., Biomed. Pharmacother., 106, 610–617 (2018). – reference: 12) Musa A. E., Shabeeb D., Okoro N. O. E., Agbele A. T., Environ. Sci. Pollut. Res. Int., 27, 33592–33600 (2020). – reference: 22) Lu X., Teng Y., Lin X., Xiao M., Liu C., Chi X., Zhang Y., Luo G., Xiang H., Bioorg. Chem., 109, 104714 (2021). – reference: 15) Huang Y., Jiao Z., Fu Y., Hou Y., Sun J., Hu F., Yu S., Gong K., Liu Y., Zhao G., Eur. J. Med. Chem., 265, 116–121 (2024). – reference: 5) Loge L., Florescu C., Alves A., Menahem B., J. Visc. Surg., 157, 475–485 (2020). – reference: 10) MacVittie T., Farese A., J. Radiol. Prot., 41, S438–S440 (2021). – reference: 8) Liu L., Liang Z., Ma S., Li L., Liu X., Mol. Med. Rep., 27, 1–14 (2023). – reference: 6) Christy B. A., Herzig M. C., Wu X., Mohammadipoor A., McDaniel J. S., Bynum J. A., Int. J. Mol. Sci., 25, 6973–6974 (2024). – reference: 27) Zuo Z., Wang L., Wang S., Liu X., Wu D., Ouyang Z., Meng R., Shan Y., Zhang S., Peng T., Wang L., Li Z., Cong Y., Eur. J. Med. Chem., 269, 116346 (2024). – reference: 26) Yin J., Hu N., Yi L., Zhao W., Cheng X., Li G., Yang N., Li G., Ding D., Health Phys., 120, 541–551 (2021). – reference: 9) Singh V., Seed T., Drugs Today (Barc.), 58, 133–145 (2022). – reference: 3) Kiang J. G., Garrison B. R., Gorbunov N. V., Adapt. Med., 2, 1–10 (2010). – reference: 14) Kang A. D., Cosenza S. C., Bonagura M., Manair M., Reddy M. V. R., Reddy E., PLOS ONE, 8, e58355–e58360 (2013). – reference: 2) Mishyna M., Volokh O., Danilova Y., Gerasimova N., Pechnikova E., Sokolova O., Micron, 96, 57–64 (2017). – reference: 20) Cui Y., He Z., Chen T., Ren X., Xu J., Zhang S., Peng T., Liu S., Wang L., Eur. J. Med. Chem., 268, 116239 (2024). – reference: 28) Arnautou P., Garnier G., Maillot J., Konopacki J., Brachet M., Bonnin A., Amabile J. C., Malfuson J. V., Transfus. Clin. Biol., 31, 253–259 (2024). – reference: 16) Feng T., Wang L., Zhou N., Liu C., Cui J., Wu R., Jing J., Zhang S., Chen H., Wang S., Oncol. Rep., 38, 3094–3102 (2017). – reference: 25) Peng T., Liu S. C., Zhang S. G., Sun Y. B., Li X. P., Xu J., Wang Lin., CN Patent Application Publication No. 116751178A (2023). – reference: 17) Ghosh S. P., Perkins M. W., Hieber K., Kulkarni S., Kao T. C., Reddy E. P., Reddy M. V., Maniar M., Seed T., Kumar K. S., Radiat. 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| Title | Design, Synthesis and Radioprotective Activity Evaluation of Novel N-Phenyl-2H-chromene-3-carboxamides Derived from Ex-RAD |
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| ispartofPNX | Chemical and Pharmaceutical Bulletin, 2025/07/10, Vol.73(7), pp.600-615 |
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