Journals / Organic Communications / 2021 / Cilt: 14 - Sayı: 3

Synthesis of novel salicylic acid-pyrrolone conjugates and investigation of their cytotoxic and genotoxic effects in Allium cepa root tip cells

Pages
280–293
Publication Date
2022-10-19
DOI
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AI Summary & Key Takeaways

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⚡ TL;DR(Too Long; Didn't Read)

As a result of cytogenetic analysis, it was determined that high concentrations of some hybrid compounds significantly reduced the number of divisions of A. cepa cells (cytotoxicity in 7a and 7c) and caused chromosomal abnormalities in dividing cells (genotoxicity in 7a, 7c, 7e, and especially 7d)

📌 3 Key Takeaways

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Objective & Hypothesis:: In the 20th century, many new drugs have been designed and synthesized to be used for therapeutic purposes.
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Key Findings & Data:In this study, the synthesis of salicylic acid-pyrrolone hybrid compounds was carried out from the reactions of furan-3-one compounds with 4-aminosalicylic acid and 5-aminosalicylic acid reagents.
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Conclusion & Impact:As a result of cytogenetic analysis, it was determined that high concentrations of some hybrid compounds significantly reduced the number of divisions of A. cepa cells (cytotoxicity in 7a and 7c) and caused chromosomal abnormalities in dividing cells (genotoxicity in 7a, 7c, 7e, and especially 7d)
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

: In the 20th century, many new drugs have been designed and synthesized to be used for therapeutic purposes. In these syntheses, especially the salicylic acid group is included in the structure of many drugs. The salicylic acid molecule is the starting material of aspirin and is a structurally important compound. There are many commercial products on the market that are synthesized from salicylic acid or contain salicylic acid group. In this study, the synthesis of salicylic acid-pyrrolone hybrid compounds was carried out from the reactions of furan-3-one compounds with 4-aminosalicylic acid and 5-aminosalicylic acid reagents. The synthesis reactions were achieved in three steps and in these synthesis, biologically active pyrrolone and salicylic acid groups were integrated. The characterizations of these compounds that were purified by column chromatography and crystallization method were made by FTIR, NMR and HRMS techniques. The cytotoxic and genotoxic potentials of the novel compounds (7a-e) were evaluated at five different concentrations (6.25, 12.5, 25, 50 and 100 μM) using the Allium test system. As a result of cytogenetic analysis, it was determined that high concentrations of some hybrid compounds significantly reduced the number of divisions of A. cepa cells (cytotoxicity in 7a and 7c) and caused chromosomal abnormalities in dividing cells (genotoxicity in 7a, 7c, 7e, and especially 7d)

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Cite This Article

EROĞLU, H. E., GÜMÜŞ, M., KOCA, İ., CAN, S. (2022). Synthesis of novel salicylic acid-pyrrolone conjugates and investigation of their cytotoxic and genotoxic effects in Allium cepa root tip cells. Organic Communications, Cilt: 14 - Sayı: 3, 280–293. https://ajindex.com/articles/585651

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References (15)

  1. Rainsford, K.D. Aspirin and Related Drugs, Taylor & Francis Ltd., London, UK., 2004, 770 pp
  2. Hedner, T.; Everts, B. The early clinical history of salicylates in rheumatology and pain. Clin. Rheumatol. 1998, 17(1), 17-25
  3. Hauso, O.; Martinsen, T.C.; Waldum, H. 5-Aminosalicylic acid, a specific drug for ulcerative colitis. Scand. J. Gastroenterol. 2015, 50(8), 933-941
  4. Omoteyama, K.; Sato, T.; Arito, M.; Sato, M.; Suematsu, N.; Kurokawa, M.S.; Kato, T. Effects of salazosulfapyridine on the profile of cell surface proteins, revealed by biotinylation of cell surface proteins and 2-dimensional electrophoresis. Biochim. Biophys. Acta Proteins Proteom. 2019, 1867(1), 47-56
  5. Seferoğlu, B.; Altaş, E.U.; Şenel, K. Antimalarials and sulfasalazine, Turkiye Klinikler. J PM&R-Special Top. 2014, 7(4), 20-24
  6. Yeonhwa, S.; Ran, S.H.; Jaewoo, J.; Tae-Hoon, S.; Mun, B.S.; Seung-Jae, M.; Mun, B.S.; Seung-Jae, M.; Jin-Sun, K.; Mo, K.K.; Seung-Jae, M.; Kyung, C. Sulfasalazine attenuates evading anticancer response of CD133-positive hepatocellular carcinoma cells. J. Exp. Clin. Cancer Res. 2017, 36(1), 38
  7. Abdu-Allah, H.H.; El-Shorbagi, A.N.A.; Abdel-Moty, S.G.; El-Awady, R.; Abdel-Alim, A.A.M
  8. Aminosalyclic acid (5-ASA): A unique anti-inflammatory salicylate. Med. Chem. 2016, 6(5), 361/1-361/10
  9. Green, J.R; Lobo, A.J.; Holdsworth, C.D.; Leicester, R.J.; Gibson, J.A.; Kerr, G.D.; Hodgson, H.J.; Parkins, K.J.; Taylor, M.D. Balsalazide is more effective and better tolerated than mesalamine in the treatment of acute ulcerative colitis. The Abacus Investigator Group, Gastroenterology 1998, 114(1), 15-22
  10. Ibrahim, M.A.; Elagawany, M.; Ibrahim, T.S. Green and catalyst-free synthesis of olsalazine analogs. Green Chem. Lett. Rev. 2016, 9(2), 91-95
  11. Pozharskii, A.K.; Ramsden, C.; Joule, J.; Zhdankin, V. Handbook of Heterocyclic Chemistry 2nd Edition, United Kingdom, Elsevier Science & Technology, 2000, 520 pp
  12. Gholap, S.S. Pyrrole: An emerging scaffold for construction of valuable therapeutic agents. Eur. J. Med. Chem. 2016, 110, 13-31
  13. Snyder, R.D.; Green, J.W. A review of the genotoxicity of marketed pharmaceuticals. Mutat. Res. 2001, 488(2), 151-69
  14. Ali, Y.; Alam, M.S.; Hamid, H.; Hussain, A. 2(3H)Pyrrolone–a biologically active scaffold. Oriental J Chem. 2014, 30(1), 1-16
  15. Mohamed, M.S.; El-Domany, R.A.; Abd El-Hameed, R.H. Synthesis of certain pyrrole derivatives as antimicrobial agents. Acta. Pharm. 2009, 59(2), 145-15