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Antibacterial and Antioxidant Activity Evaluation of Bis-Substituted İsovanillin Derivatives

Yıl 2023, Cilt: 10 Sayı: 2, 435 - 442, 31.05.2023
https://doi.org/10.18596/jotcsa.1196335

Öz

Herein, a series of twelve bis-hydrazone substituted isovanilline derivatives 3(a-l), were freshly re-synthesized by the reaction of bis-aldehydes with substituted hydrazide derivatives since these compounds previously showed potent aldose reductase inhibition properties. The obtained compounds were tested for their potential antibacterial and antioxidant activities. In the present study, four different bacterial strains were used, including Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and Gram-negative (Pseudomonas aeruginosa ATCC 10231, Escherichia coli ATCC 25912). On the other hand, the antioxidant capacities of freshly re-synthesized bis-hydrazone substituted isovanilline derivatives were determined by using several antioxidant methods, including DPPH free radical scanvenging, TEAC cupric reducing (CUPRAC) and metal chelating activity methods. Several lead molecules were discovered as a potential bacterial inhibitors against S. aureus and E. coli bacterial strains. More specifically, compounds 3g (R=-H) and 3j (R= -4Cl) showed great inhibition properties against E. coli bacterial strains by having MIC values of 1.56 and 6.25 µg/mL, respectively. Moreover, none of the compounds showed potent antioxidant activity against tested methods with respect to compared standards.

Destekleyen Kurum

Istanbul Technical University Grants Commission

Proje Numarası

33467

Teşekkür

This work was partially funded by the Istanbul Technical University Grants Commission for a research grant (Project Grant No: 33467).

Kaynakça

  • 1. Doron S, Gorbach SL. Bacterial Infections: Overview. In: International Encyclopedia of Public Health [Internet]. Elsevier; 2008. p. 273–82.
  • 2. Nikaido H. Multidrug Resistance in Bacteria. Annu Rev Biochem [Internet]. 2009 Jun 1;78(1):119–46.
  • 3. Holmes AH, Moore LSP, Sundsfjord A, Steinbakk M, Regmi S, Karkey A, et al. Understanding the mechanisms and drivers of antimicrobial resistance. Lancet [Internet]. 2016 Jan 9;387(10014):176–87.
  • 4. Brown ED, Wright GD. Antibacterial drug discovery in the resistance era. Nature [Internet]. 2016 Jan 20;529(7586):336–43.
  • 5. Atanasov AG, Zotchev SB, Dirsch VM, Supuran CT. Natural products in drug discovery: advances and opportunities. Nat Rev Drug Discov [Internet]. 2021 Mar 28;20(3):200–16.
  • 6. Yang L, Feng F, Gao Y. Chemical constituents from herb of Solanum lyratum. China J Chinese Mater medica [Internet]. 2009;34(14):1805–8.
  • 7. Xu J, Tan N, Zeng G, Han H, Huang H, Ji C, et al. Studies on chemical constituents in fruit of Alpinia oxyphylla. China J Chinese Mater medica [Internet]. 2009;34(8):990–3.
  • 8. Chen W, Tang S, Qin N, Zhai H, Duan H. Antioxidant constituents from Smilax riparia. China J Chinese Mater medica [Internet]. 2012;37(6):806–10.
  • 9. Khaliq-uz-Zaman S., Simin K, Ahmad V. Chemical constituents from Asparagus dumosus. Fitoterapia [Internet]. 2000 Jun;71(3):331–3.
  • 10. Huang W-B, Du C-Y, Jiang J-A, Ji Y-F. Concurrent synthesis of vanillin and isovanillin. Res Chem Intermed [Internet]. 2013 Jul 26;39(6):2849–56.
  • 11. Saari WS, Freedman MB, Hartman RD, King SW, Raab AW, Randall WC, et al. Synthesis and antihypertensive activity of some ester progenitors of methyldopa. J Med Chem [Internet]. 1978 Aug 1;21(8):746–53.
  • 12. Uchida K, Yokoshima S, Kan T, Fukuyama T. Total Synthesis of (±)-Morphine. Org Lett [Internet]. 2006 Nov 9;8(23):5311–3.
  • 13. Marco-Contelles J, do Carmo Carreiras M, Rodríguez C, Villarroya M, García AG. Synthesis and Pharmacology of Galantamine. Chem Rev [Internet]. 2006 Jan 1;106(1):116–33.
  • 14. Adam F, Hamdan MA, Abu Bakar SH, Yusoff MM, Jose R. Molecular recognition of isovanillin crosslinked carrageenan biocomposite for drug delivery application. Chem Eng Commun [Internet]. 2021 May 4;208(5):741–52.
  • 15. Cole C, Burgoyne T, Lee A, Stehno-Bittel L, Zaid G. Arum Palaestinum with isovanillin, linolenic acid and β-sitosterol inhibits prostate cancer spheroids and reduces the growth rate of prostate tumors in mice. BMC Complement Altern Med [Internet]. 2015 Dec 5;15(1):264.
  • 16. Oketch-Rabah HA. Mondia whitei , a Medicinal Plant from Africa with Aphrodisiac and Antidepressant Properties: A Review. J Diet Suppl [Internet]. 2012 Nov 13;9(4):272–84.
  • 17. Dimo T, Rakotonirina S V, Tan P V, Azay J, Dongo E, Cros G. Leaf methanol extract of Bidens pilosa prevents and attenuates the hypertension induced by high-fructose diet in Wistar rats. J Ethnopharmacol [Internet]. 2002 Dec;83(3):183–91.
  • 18. Sadraei H, Ghanadian M, Asghari G, Azali N. Antidiarrheal activities of isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice. Res Pharm Sci [Internet]. 2014;9(2):83–9.
  • 19. Verma G, Marella A, Shaquiquzzaman M, Akhtar M, Ali M, Alam M. A review exploring biological activities of hydrazones. J Pharm Bioallied Sci [Internet]. 2014;6(2):69–80.
  • 20. Rollas S, Küçükgüzel S. Biological Activities of Hydrazone Derivatives. Molecules [Internet]. 2007 Aug 17;12(8):1910–39.
  • 21. Narang R, Narasimhan B, Sharma S. A Review on Biological Activities and Chemical Synthesis of Hydrazide Derivatives. Curr Med Chem [Internet]. 2012 Feb 1;19(4):569–612.
  • 22. Negi VJ, Sahrma AK, Negi JS, Ram V. Biological Activities of Hydrazone Derivatives in the New Millennium. Int J Pharm Chem [Internet]. 2012 Jan 1;2(4):100–9.
  • 23. Akocak S, Alam MR, Shabana AM, Sanku RKK, Vullo D, Thompson H, et al. PEGylated Bis-Sulfonamide Carbonic Anhydrase Inhibitors Can Efficiently Control the Growth of Several Carbonic Anhydrase IX-Expressing Carcinomas. J Med Chem [Internet]. 2016 May 26;59(10):5077–88.
  • 24. Akocak S, Lolak N, Nocentini A, Karakoc G, Tufan A, Supuran CT. Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. Bioorg Med Chem [Internet]. 2017 Jun 15;25(12):3093–7.
  • 25. Akocak S, Lolak N, Bua S, Nocentini A, Supuran CT. Activation of human α-carbonic anhydrase isoforms I, II, IV and VII with bis-histamine schiff bases and bis-spinaceamine substituted derivatives. J Enzyme Inhib Med Chem [Internet]. 2019 Jan 1;34(1):1193–8.
  • 26. Lolak N, Akocak S, Türkeş C, Taslimi P, Işık M, Beydemir Ş, et al. Synthesis, characterization, inhibition effects, and molecular docking studies as acetylcholinesterase, α-glycosidase, and carbonic anhydrase inhibitors of novel benzenesulfonamides incorporating 1,3,5-triazine structural motifs. Bioorg Chem [Internet]. 2020 Jul 1;100:103897.
  • 27. Lolak N, Akocak S, Durgun M, Duran HE, Necip A, Türkeş C, et al. Novel bis-ureido-substituted sulfaguanidines and sulfisoxazoles as carbonic anhydrase and acetylcholinesterase inhibitors. Mol Divers [Internet]. 2022 Sep 22 [cited 2023 Mar 23];Article in:1–15.
  • 28. Yapar G, Esra Duran H, Lolak N, Akocak S, Türkeş C, Durgun M, et al. Biological effects of bis-hydrazone compounds bearing isovanillin moiety on the aldose reductase. Bioorg Chem [Internet]. 2021 Dec 1;117:105473.
  • 29. Al-blewi FF, Almehmadi MA, Aouad MR, Bardaweel SK, Sahu PK, Messali M, et al. Design, synthesis, ADME prediction and pharmacological evaluation of novel benzimidazole-1,2,3-triazole-sulfonamide hybrids as antimicrobial and antiproliferative agents. Chem Cent J [Internet]. 2018 Dec 1;12(1):110.
  • 30. Tekeli Y, Lolak N, Sonmez GD, Tekeli T, Akocak S. Antibacterial, Antioxidant and DNA Cleavage Activity Evaluation of Substituted Phenylureido Sulfaguanidine and Sulfamethazine Derivatives. Pharm Chem J [Internet]. 2022 Jun 26;56(3):345–9.
  • 31. Boga M, Tekeli Y, Lolak N, Sonmez GD, Akocak S. Synthesis and Antibacterial, Antioxidant and DNA Cleavage Evaluation of Triazenes Containing Sulfathiazole Moiety. Nov Approaches Drug Des Dev [Internet]. 2022 Jan 11;6(1):555684.
  • 32. BLOIS MS. Antioxidant Determinations by the Use of a Stable Free Radical. Nature [Internet]. 1958 Apr;181:1199–200.
  • 33. Carter P. Spectrophotometric determination of serum iron at the submicrogram level with a new reagent (ferrozine). Anal Biochem [Internet]. 1971 Apr 1;40(2):450–8.
  • 34. Apak R, Güçlü K, Özyürek M, Karademir SE. Novel Total Antioxidant Capacity Index for Dietary Polyphenols and Vitamins C and E, Using Their Cupric Ion Reducing Capability in the Presence of Neocuproine: CUPRAC Method. J Agric Food Chem [Internet]. 2004 Dec 1;52(26):7970–81.
Yıl 2023, Cilt: 10 Sayı: 2, 435 - 442, 31.05.2023
https://doi.org/10.18596/jotcsa.1196335

Öz

Proje Numarası

33467

Kaynakça

  • 1. Doron S, Gorbach SL. Bacterial Infections: Overview. In: International Encyclopedia of Public Health [Internet]. Elsevier; 2008. p. 273–82.
  • 2. Nikaido H. Multidrug Resistance in Bacteria. Annu Rev Biochem [Internet]. 2009 Jun 1;78(1):119–46.
  • 3. Holmes AH, Moore LSP, Sundsfjord A, Steinbakk M, Regmi S, Karkey A, et al. Understanding the mechanisms and drivers of antimicrobial resistance. Lancet [Internet]. 2016 Jan 9;387(10014):176–87.
  • 4. Brown ED, Wright GD. Antibacterial drug discovery in the resistance era. Nature [Internet]. 2016 Jan 20;529(7586):336–43.
  • 5. Atanasov AG, Zotchev SB, Dirsch VM, Supuran CT. Natural products in drug discovery: advances and opportunities. Nat Rev Drug Discov [Internet]. 2021 Mar 28;20(3):200–16.
  • 6. Yang L, Feng F, Gao Y. Chemical constituents from herb of Solanum lyratum. China J Chinese Mater medica [Internet]. 2009;34(14):1805–8.
  • 7. Xu J, Tan N, Zeng G, Han H, Huang H, Ji C, et al. Studies on chemical constituents in fruit of Alpinia oxyphylla. China J Chinese Mater medica [Internet]. 2009;34(8):990–3.
  • 8. Chen W, Tang S, Qin N, Zhai H, Duan H. Antioxidant constituents from Smilax riparia. China J Chinese Mater medica [Internet]. 2012;37(6):806–10.
  • 9. Khaliq-uz-Zaman S., Simin K, Ahmad V. Chemical constituents from Asparagus dumosus. Fitoterapia [Internet]. 2000 Jun;71(3):331–3.
  • 10. Huang W-B, Du C-Y, Jiang J-A, Ji Y-F. Concurrent synthesis of vanillin and isovanillin. Res Chem Intermed [Internet]. 2013 Jul 26;39(6):2849–56.
  • 11. Saari WS, Freedman MB, Hartman RD, King SW, Raab AW, Randall WC, et al. Synthesis and antihypertensive activity of some ester progenitors of methyldopa. J Med Chem [Internet]. 1978 Aug 1;21(8):746–53.
  • 12. Uchida K, Yokoshima S, Kan T, Fukuyama T. Total Synthesis of (±)-Morphine. Org Lett [Internet]. 2006 Nov 9;8(23):5311–3.
  • 13. Marco-Contelles J, do Carmo Carreiras M, Rodríguez C, Villarroya M, García AG. Synthesis and Pharmacology of Galantamine. Chem Rev [Internet]. 2006 Jan 1;106(1):116–33.
  • 14. Adam F, Hamdan MA, Abu Bakar SH, Yusoff MM, Jose R. Molecular recognition of isovanillin crosslinked carrageenan biocomposite for drug delivery application. Chem Eng Commun [Internet]. 2021 May 4;208(5):741–52.
  • 15. Cole C, Burgoyne T, Lee A, Stehno-Bittel L, Zaid G. Arum Palaestinum with isovanillin, linolenic acid and β-sitosterol inhibits prostate cancer spheroids and reduces the growth rate of prostate tumors in mice. BMC Complement Altern Med [Internet]. 2015 Dec 5;15(1):264.
  • 16. Oketch-Rabah HA. Mondia whitei , a Medicinal Plant from Africa with Aphrodisiac and Antidepressant Properties: A Review. J Diet Suppl [Internet]. 2012 Nov 13;9(4):272–84.
  • 17. Dimo T, Rakotonirina S V, Tan P V, Azay J, Dongo E, Cros G. Leaf methanol extract of Bidens pilosa prevents and attenuates the hypertension induced by high-fructose diet in Wistar rats. J Ethnopharmacol [Internet]. 2002 Dec;83(3):183–91.
  • 18. Sadraei H, Ghanadian M, Asghari G, Azali N. Antidiarrheal activities of isovanillin, iso-acetovanillon and Pycnocycla spinosa Decne ex.Boiss extract in mice. Res Pharm Sci [Internet]. 2014;9(2):83–9.
  • 19. Verma G, Marella A, Shaquiquzzaman M, Akhtar M, Ali M, Alam M. A review exploring biological activities of hydrazones. J Pharm Bioallied Sci [Internet]. 2014;6(2):69–80.
  • 20. Rollas S, Küçükgüzel S. Biological Activities of Hydrazone Derivatives. Molecules [Internet]. 2007 Aug 17;12(8):1910–39.
  • 21. Narang R, Narasimhan B, Sharma S. A Review on Biological Activities and Chemical Synthesis of Hydrazide Derivatives. Curr Med Chem [Internet]. 2012 Feb 1;19(4):569–612.
  • 22. Negi VJ, Sahrma AK, Negi JS, Ram V. Biological Activities of Hydrazone Derivatives in the New Millennium. Int J Pharm Chem [Internet]. 2012 Jan 1;2(4):100–9.
  • 23. Akocak S, Alam MR, Shabana AM, Sanku RKK, Vullo D, Thompson H, et al. PEGylated Bis-Sulfonamide Carbonic Anhydrase Inhibitors Can Efficiently Control the Growth of Several Carbonic Anhydrase IX-Expressing Carcinomas. J Med Chem [Internet]. 2016 May 26;59(10):5077–88.
  • 24. Akocak S, Lolak N, Nocentini A, Karakoc G, Tufan A, Supuran CT. Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors. Bioorg Med Chem [Internet]. 2017 Jun 15;25(12):3093–7.
  • 25. Akocak S, Lolak N, Bua S, Nocentini A, Supuran CT. Activation of human α-carbonic anhydrase isoforms I, II, IV and VII with bis-histamine schiff bases and bis-spinaceamine substituted derivatives. J Enzyme Inhib Med Chem [Internet]. 2019 Jan 1;34(1):1193–8.
  • 26. Lolak N, Akocak S, Türkeş C, Taslimi P, Işık M, Beydemir Ş, et al. Synthesis, characterization, inhibition effects, and molecular docking studies as acetylcholinesterase, α-glycosidase, and carbonic anhydrase inhibitors of novel benzenesulfonamides incorporating 1,3,5-triazine structural motifs. Bioorg Chem [Internet]. 2020 Jul 1;100:103897.
  • 27. Lolak N, Akocak S, Durgun M, Duran HE, Necip A, Türkeş C, et al. Novel bis-ureido-substituted sulfaguanidines and sulfisoxazoles as carbonic anhydrase and acetylcholinesterase inhibitors. Mol Divers [Internet]. 2022 Sep 22 [cited 2023 Mar 23];Article in:1–15.
  • 28. Yapar G, Esra Duran H, Lolak N, Akocak S, Türkeş C, Durgun M, et al. Biological effects of bis-hydrazone compounds bearing isovanillin moiety on the aldose reductase. Bioorg Chem [Internet]. 2021 Dec 1;117:105473.
  • 29. Al-blewi FF, Almehmadi MA, Aouad MR, Bardaweel SK, Sahu PK, Messali M, et al. Design, synthesis, ADME prediction and pharmacological evaluation of novel benzimidazole-1,2,3-triazole-sulfonamide hybrids as antimicrobial and antiproliferative agents. Chem Cent J [Internet]. 2018 Dec 1;12(1):110.
  • 30. Tekeli Y, Lolak N, Sonmez GD, Tekeli T, Akocak S. Antibacterial, Antioxidant and DNA Cleavage Activity Evaluation of Substituted Phenylureido Sulfaguanidine and Sulfamethazine Derivatives. Pharm Chem J [Internet]. 2022 Jun 26;56(3):345–9.
  • 31. Boga M, Tekeli Y, Lolak N, Sonmez GD, Akocak S. Synthesis and Antibacterial, Antioxidant and DNA Cleavage Evaluation of Triazenes Containing Sulfathiazole Moiety. Nov Approaches Drug Des Dev [Internet]. 2022 Jan 11;6(1):555684.
  • 32. BLOIS MS. Antioxidant Determinations by the Use of a Stable Free Radical. Nature [Internet]. 1958 Apr;181:1199–200.
  • 33. Carter P. Spectrophotometric determination of serum iron at the submicrogram level with a new reagent (ferrozine). Anal Biochem [Internet]. 1971 Apr 1;40(2):450–8.
  • 34. Apak R, Güçlü K, Özyürek M, Karademir SE. Novel Total Antioxidant Capacity Index for Dietary Polyphenols and Vitamins C and E, Using Their Cupric Ion Reducing Capability in the Presence of Neocuproine: CUPRAC Method. J Agric Food Chem [Internet]. 2004 Dec 1;52(26):7970–81.
Toplam 34 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Biyokimya ve Hücre Biyolojisi (Diğer)
Bölüm ARAŞTIRMA MAKALELERİ
Yazarlar

Zehra Tekin 0000-0003-3682-3044

Yener Tekeli 0000-0003-1524-457X

Zehra Küçükbay 0000-0001-7784-4138

Nebih Lolak 0000-0003-0578-2761

Gönül Yapar 0000-0001-5644-3300

Süleyman Akocak 0000-0003-4506-5265

Proje Numarası 33467
Yayımlanma Tarihi 31 Mayıs 2023
Gönderilme Tarihi 29 Ekim 2022
Kabul Tarihi 16 Şubat 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 10 Sayı: 2

Kaynak Göster

Vancouver Tekin Z, Tekeli Y, Küçükbay Z, Lolak N, Yapar G, Akocak S. Antibacterial and Antioxidant Activity Evaluation of Bis-Substituted İsovanillin Derivatives. JOTCSA. 2023;10(2):435-42.