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Study of Binding Properties Between Two New Ibuprofen and Naproxen Based Acyl Hydrazone Derivatives and Trypsin

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Abstract

Two acyl hydrazone derivatives, AHI and AHN, made from ibuprofen and naproxen-derived hydrazides, were prepared and studied of binding properties with serine protease trypsin by UV-vis absorption and fluorescence quenching at pH 7.4. The results suggest that both hydrazones can interact strongly with trypsin and there are the formation of trypsin-hydrazone complexes. The Stern-Volmer constants, binding constants, binding sites and the corresponding thermodynamic parameters ΔHo, ΔSo and ΔGo were calculated at different temperatures. The effect of common metal ions on the constants was also discussed. The binding modes can be explained on the basis of hydrogen bonds and van der Waals forces. The binding distance (r) ~3 nm between the donor (trypsin) and acceptors (AHI and AHN) was obtained according to Förster’s non-radiative energy transfer theory. Moreover, LOD and LOQ of hydrazones were calculated in the presence of trypsin.

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References

  1. Dugowson CE, Gnanashanmugam P (2006) Nonsteroidal anti-inflammatory drugs. Phys Med Rehabil Clin N Am 17:347–354

    Article  PubMed  Google Scholar 

  2. Klasser GD, Epstein J (2005) Nonsteroidal anti-inflammatory drugs: confusion, controversy and dental implications. J Can Dent Assoc 71:575–580

    PubMed  Google Scholar 

  3. Uzgören Baran A, Tel BC, Sarıgöl D, Öztürk EI, Kazkayası I, Okay G, Ertan M, Tozkoparan B (2012) Thiazolo[3,2-b]-1,2,4-triazole-5(6 H)-one substituted with ibuprofen: novel non-steroidal anti-inflammatory agents with favorable gastrointestinal tolerance. Eur J Med Chem 57:398–406

    Article  PubMed  Google Scholar 

  4. Rocha GM, Michea LF, Peters EM, Kirby M, Xu Y, Ferguson DR, Burg MB (2001) Direct toxicity of nonsteroidal antiinflammatory drugs for renal medullary cells. Proc Natl Acad Sci U S A 98:5317–5322

    Article  PubMed  CAS  PubMed Central  Google Scholar 

  5. Wu L-M, Teng H-B, Ke X-B, Xu W-J, J-Tu S, Liang S-C, Hu X-M (2007) Copper(II) complexes of salicylaldehyde hydrazones: synthesis, structure, and DNA interaction. Chem Biodivers 4:2198–2209

    Article  PubMed  CAS  Google Scholar 

  6. Todeschini AR, de Miranda ALP, da Silva KCM, Parrini SC, Barreiro EJ (1998) Synthesis and evaluation of analgesic, antiinflammatory and antiplatelet of new 2-pyridylarylhydrazone derivatives. Eur J Med Chem 33:189–199

    Article  CAS  Google Scholar 

  7. Melnyk P, Leroux V, Sergheraert C, Grellier P (2006) Design, synthesis and in vitro antimalarial activity of an acylhydrazone library. Bioorg Med Chem Lett 16:31–35

    Article  PubMed  CAS  Google Scholar 

  8. Küçükgüzel SG, Rollas S, Küçükgüzel I, Kiraz M (1999) Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones. Eur J Med Chem 34:1093–1100

    Article  Google Scholar 

  9. Loncle C, Brunel JM, Vidal N, Dherbomez M, Letourneux Y (2004) Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur J Med Chem 39:1067–1071

    Article  PubMed  CAS  Google Scholar 

  10. Papakonstantinou-Garoufalias S, Pouli N, Marakos P, Chytyroglou-Ladas A (2002) Synthesis antimicrobial and antifungal activity of some new 3-substituted derivatives of 4-(2,4-dichlorophenyl)-5-adamantyl-1 H-1,2,4-triazole. Farmaco 57:973–977

    Article  PubMed  CAS  Google Scholar 

  11. Vicini P, Zani F, Cozzini P, Doytchinova I (2002) Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations. Eur J Med Chem 37:553–564

    Article  PubMed  CAS  Google Scholar 

  12. Küçükgüzel SG, Mazi A, Şahin F, Öztürk S, Stables J (2003) Synthesis and biological activities of diflunisal hydrazide-hydrazones. Eur J Med Chem 38:1005–1013

    Article  PubMed  Google Scholar 

  13. Patole J, Sandbhor U, Padhye S, Deobagkar DN, Anson CE, Powell A (2003) Structural chemistry and in vitro antitubercular activity of acetylpyridine benzoyl hydrazone and its copper complex against Mycobacterium smegmatis. Bioorg Med Chem Lett 13:51–55

    Article  PubMed  CAS  Google Scholar 

  14. Chai J, Xu Q, Dai J, Liu R (2013) Investigation on potential enzyme toxicity of clenbuterol to trypsin. Spectrochim Acta Part A 105:200–206

    Article  CAS  Google Scholar 

  15. Zhang H-M, Wang Y-Q, Zhou Q-H (2009) Investigation of the interactions of quercetin and Morin with trypsin. Luminescence 24:355–362

    Article  PubMed  CAS  Google Scholar 

  16. Wang Y-Q, Chen T-T, Zhang H-M (2010) Investigation of the interactions of lysozyme and trypsin with biphenol a using spectroscopic methods. Spectrochim Acta Part A 75:1130–1137

    Article  Google Scholar 

  17. Gökoğlu E, Yılmaz E (2014) Fluorescence interaction and determination of sulfathiazole with trypsin. J Fluoresc 24:1439–1445

    Article  PubMed  Google Scholar 

  18. Wang Y-Q, Tan C-Y, Zhuang S-L, Zhai P-Z, Cui Y, Zhou Q-H, Zhang H-M, Fei Z (2014) In vitro and in silico investigations of the binding interactionsbetween chlorophenols and trypsin. J Hazard Mater 278:55–65

    Article  PubMed  CAS  Google Scholar 

  19. He W, Dou H, Zhang L, Wang L, Wang R, Chang J (2014) Spectroscopic study on the interaction of trypsin with bicyclol and analogs. Spectrochim Acta Part A 118:510–519

    Article  CAS  Google Scholar 

  20. Zhang H-M, Zhou Q-H, Wang Y-Q (2010) Studies on the interactions of 2, 4-dinitrophenol and 2, 4-dichlorphenol with trypsin. J Fluoresc 20:507–516

    Article  PubMed  CAS  Google Scholar 

  21. Kawai S, Kojima F, Kusunoki N (2005) Recent advances in nonsteroidal anti-inflammatory drugs. Allergol Int 54:209–215

    Article  CAS  Google Scholar 

  22. Kalgutkar AS, Crews BC, Marnett LJ (1996) Kinetics of the interaction of nonsteroidal antiinflammatory drugs with prostaglandin endoperoxide synthase-1 studied by limited proteolysis. Biochemistry 35:9076–9082

    Article  PubMed  CAS  Google Scholar 

  23. Uzgören Baran A (2013) Comparative study of microwave-assisted and conventional synthesis of ibuprofen-based acyl hydrazone derivatives. Turk J Chem 37:927–935

    Article  Google Scholar 

  24. Lakowicz JR (2006) Principles of fluorescence spectroscopy. Plenum, New York

    Book  Google Scholar 

  25. Zhang H-M, Wang Y-Q, Zhou Q-H (2010) Fluorimetric study of interaction of benzidine with trypsin. J Lumin 130:781–786

    Article  CAS  Google Scholar 

  26. Lu Y, Wang G, Lu X, Lv J, Xu M, Zhang W (2010) Molecular mechanism of interaction between norfloxacin and trypsin studied by molecular spectroscopy and modeling. Spectrochim Acta Part A 75:261–266

    Article  Google Scholar 

  27. Li D, Zhang T, Ji B (2014) Influences of pH, urea and metal ions on the interaction of sinomenine with lysozyme by steady state fluorescence spectroscopy. Spectrochim Acta Part A 130:440–446

    Article  CAS  Google Scholar 

  28. Ross PD, Subramanian S (1981) Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 20:3096–3102

    Article  PubMed  CAS  Google Scholar 

  29. Sahoo H (2011) Förster resonance energy transfer-a spectroscopic nanoruler: principle and applications (review). J Photochem Photobiol C: Photochem Rev 12:20–30

    Article  CAS  Google Scholar 

  30. Bhattar SL, Kolekar GB, Patil SR (2008) Fluorescence resonance energy transfer between perylene and riboflavin in micellar solution and analytical application on determination of vitamin B2. J Lumin 128:306–310

    Article  CAS  Google Scholar 

  31. Deepa S, Mishra AK (2005) Fluorescence spectroscopic study of serum albümin-bromadiolone interaction: fluorimetric determination of bromadiolone. J Pharm Biomed Anal 38:556–563

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Hacettepe University, 06800, Ankara, Turkey

    Elmas Gökoğlu, Esra Yılmaz, Esra Gökoğlu & Ayşe Uzgören Baran

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  1. Elmas Gökoğlu
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  2. Esra Yılmaz
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  3. Esra Gökoğlu
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  4. Ayşe Uzgören Baran
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Correspondence to Elmas Gökoğlu.

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Gökoğlu, E., Yılmaz, E., Gökoğlu, E. et al. Study of Binding Properties Between Two New Ibuprofen and Naproxen Based Acyl Hydrazone Derivatives and Trypsin. J Fluoresc 26, 113–119 (2016). https://doi.org/10.1007/s10895-015-1690-2

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  • DOI: https://doi.org/10.1007/s10895-015-1690-2

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