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Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents

Year 2019, Volume: 78 Issue: 2, 117 - 123, 06.12.2019

Abstract

Objective: Naphthoquinone derivatives are known to have antibacterial activity and are likely to succeed a new class of compound that can be applied as antimicrobial agents. Materials and Methods: The purpose of this experiment was to evaluate the potential antimicrobial, antibiofilm, anticancer, and cytotoxic activities of six naphthoquinone compounds previously reported in the literature. Results: According to our studies, 2-(4-(trifluoromethyl)phenylamino)-3-(propylthio)naphthalene-1,4-dione (5a) and 2-(4-(trifluoromethyl)phenylamino)-3-(pentylthio)naphthalene-1,4-dione (5b) were found to have good antimicrobial activity against Staphylococcus aureus ATCC 29213 with 1.22 and 19.53 µg/mL MIC values, respectively. When we carried out the test against biofilm, the most effective agent, 5a, showed up to 40% inhibition of the S. aureus’s biofilm at the 1 x MIC concentration. However, when we investigated the cytotoxic effect of 5a on the cancer and non-cancer cell lines, we found that 5a showed higher toxicity to cancer cell lines. Conclusion: The findings of our study suggest that further studies to develop these compounds and investigate its pharmacological properties could be useful to define the functionality of them as antimicrobial or anticancer agents. 

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References

  • 1. Ryu CK, Shim JY, Chae MJ, Choi IH, Han JY, Jung OJ, et al. Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5hydroxy-/5-methoxy-1,4-naphthoquinones. Eur J Med Chem 2005; 40 (5): 438-44.
  • 2. Bayrak N, Yıldırım H, Tuyun AF, Mataracı-Kara E, Ozbek-Celik B, Gupta GK, et al. Synthesis, computational study, and evaluation of in vitro antimicrobial, antibiofilm, and anticancer activities of new sulfanyl aminonaphthoquinone derivatives. Lett Drug Des Discov 2016; 13 (999).
  • 3. Ryu CK, Lee JY, Jeong SH, Nho JH. Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo4,9-dihydro-1H-benzo[f]indoles. Bioorg Med Chem Lett 2009; 19: 146–8.
  • 4. Yıldırım H, Bayrak N, Tuyun AF, Mataracı-Kara E, Ozbek-Celik, B, Gupta GK. 2,3-disubstituted-1,4-naphthoquinones containing an arylamine with trifluoromethyl group: synthesis, biological evaluation, and computational study. Rsc Adv 2017; 7: 25753-64.
  • 5. Kacmaz A, Acar ET, Atun G, Kaya K, Sigirci BD, Bagcigil F. Synthesis, electrochemistry, DFT calculations, antimicrobial properties and X-ray crystal structures of some NH- and/or S- substituted-1,4quinones. Chemistryselect 2018; 3: 8615-23.
  • 6. Errante G, Motta GL, Lagana C, Wittebolle V, Sarciron MÉ, Barret R. Synthesis and evaluation of antifungal activity of naphthoquinone derivatives. Eur J Med Chem 2006; 41: 773–8. 7. Bayrak N. Novel straight-chained sulfanyl members of arylamino1,4-naphthoquinones: synthesis and characterization. JOTCSA 2017; 4(2): 597-606.
  • 8. Clinical and Laboratory Standards Institute (CLSI), Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, in, Wayne, PA, USA, 2006.
  • 9. Clinical and Laboratory Standards Institute (CLSI), Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard–Second Edition, in, Wayne, PA, USA, 1997.
  • 10. Mataracı E, Döşler S. In vitro activities of antibiotics and antimicrobial cationic peptides alone and in combination against methicillin resistant Staphylococcus aureus biofilms. Antimicrob Agents Chemother 2012; 56: 6366-71.
  • 11. National Committee for Clinical Laboratory Standards. Methods for Determining Bactericidal Activity of Antimicrobial Agents- Approved Guideline M26 A. Wayne NCCLS, 1999.
  • 12. Cepas V, López Y, Muñoz E, Rolo D, Ardanuy C, Martí S, et al. Relationship between biofilm formation and antimicrobial resistance in gram-negative bacteria. Microb Drug Resist 2019; 25(1): 72-9.
  • 13. Döşler S, Mataracı-Kara E, Başpinar Küçük H, Yusufoğlu AS. Antibacterial and anti-biofilm activities of new chiral and racemic 1,3-dioxolanes. Istanbul J Pharm 2015; 45(1): 19-28.
  • 14. Calderone R, Sun N, Gay-Andrieu F, Groutas W, Weerawarna P, Prasad S, et al. Antifungal drug discovery: the process and outcomes. Future Microbiol 2014; 9: 791-805.
  • 15. Nigam A, Gupta D, Sharma A. Treatment of infectious disease: Beyond antibiotics. Microbiol Res 2014; 169: 643-51.
  • 16. Mosolygó T, Kincses A, Csonka A, Tönki ÁS, Witek K, Sanmartín C, et al. Selenocompounds as novel antibacterial agents and bacterial efflux pump inhibitors. Molecules 2019; 24: 1487.
  • 17. Jamal M, Ahmad W, Andleeb S, Jalil F, Imran M, Nawaz MA, et al. Bacterial biofilm and associated infections. J Chin Med Assoc 2018; 81(1): 7-11.
  • 18. Donlan RM, Costerton JW. Biofilms: survival mechanisms of clinically relevant microorganisms. Clin Microbiol Rev 2002; 15: 167-93.
  • 19. Hoiby N, Bjarnsholt T, Moser C, Bassi GL, Coenye T, Donelli G, et al. ESCMID guideline for the diagnosis and treatment of biofilm infections 2014. Clin Microbiol Infect 2015; 21(S1): S1-S25.
Year 2019, Volume: 78 Issue: 2, 117 - 123, 06.12.2019

Abstract

References

  • 1. Ryu CK, Shim JY, Chae MJ, Choi IH, Han JY, Jung OJ, et al. Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5hydroxy-/5-methoxy-1,4-naphthoquinones. Eur J Med Chem 2005; 40 (5): 438-44.
  • 2. Bayrak N, Yıldırım H, Tuyun AF, Mataracı-Kara E, Ozbek-Celik B, Gupta GK, et al. Synthesis, computational study, and evaluation of in vitro antimicrobial, antibiofilm, and anticancer activities of new sulfanyl aminonaphthoquinone derivatives. Lett Drug Des Discov 2016; 13 (999).
  • 3. Ryu CK, Lee JY, Jeong SH, Nho JH. Synthesis and antifungal activity of 1H-pyrrolo[3,2-g]quinoline-4,9-diones and 4,9-dioxo4,9-dihydro-1H-benzo[f]indoles. Bioorg Med Chem Lett 2009; 19: 146–8.
  • 4. Yıldırım H, Bayrak N, Tuyun AF, Mataracı-Kara E, Ozbek-Celik, B, Gupta GK. 2,3-disubstituted-1,4-naphthoquinones containing an arylamine with trifluoromethyl group: synthesis, biological evaluation, and computational study. Rsc Adv 2017; 7: 25753-64.
  • 5. Kacmaz A, Acar ET, Atun G, Kaya K, Sigirci BD, Bagcigil F. Synthesis, electrochemistry, DFT calculations, antimicrobial properties and X-ray crystal structures of some NH- and/or S- substituted-1,4quinones. Chemistryselect 2018; 3: 8615-23.
  • 6. Errante G, Motta GL, Lagana C, Wittebolle V, Sarciron MÉ, Barret R. Synthesis and evaluation of antifungal activity of naphthoquinone derivatives. Eur J Med Chem 2006; 41: 773–8. 7. Bayrak N. Novel straight-chained sulfanyl members of arylamino1,4-naphthoquinones: synthesis and characterization. JOTCSA 2017; 4(2): 597-606.
  • 8. Clinical and Laboratory Standards Institute (CLSI), Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, in, Wayne, PA, USA, 2006.
  • 9. Clinical and Laboratory Standards Institute (CLSI), Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard–Second Edition, in, Wayne, PA, USA, 1997.
  • 10. Mataracı E, Döşler S. In vitro activities of antibiotics and antimicrobial cationic peptides alone and in combination against methicillin resistant Staphylococcus aureus biofilms. Antimicrob Agents Chemother 2012; 56: 6366-71.
  • 11. National Committee for Clinical Laboratory Standards. Methods for Determining Bactericidal Activity of Antimicrobial Agents- Approved Guideline M26 A. Wayne NCCLS, 1999.
  • 12. Cepas V, López Y, Muñoz E, Rolo D, Ardanuy C, Martí S, et al. Relationship between biofilm formation and antimicrobial resistance in gram-negative bacteria. Microb Drug Resist 2019; 25(1): 72-9.
  • 13. Döşler S, Mataracı-Kara E, Başpinar Küçük H, Yusufoğlu AS. Antibacterial and anti-biofilm activities of new chiral and racemic 1,3-dioxolanes. Istanbul J Pharm 2015; 45(1): 19-28.
  • 14. Calderone R, Sun N, Gay-Andrieu F, Groutas W, Weerawarna P, Prasad S, et al. Antifungal drug discovery: the process and outcomes. Future Microbiol 2014; 9: 791-805.
  • 15. Nigam A, Gupta D, Sharma A. Treatment of infectious disease: Beyond antibiotics. Microbiol Res 2014; 169: 643-51.
  • 16. Mosolygó T, Kincses A, Csonka A, Tönki ÁS, Witek K, Sanmartín C, et al. Selenocompounds as novel antibacterial agents and bacterial efflux pump inhibitors. Molecules 2019; 24: 1487.
  • 17. Jamal M, Ahmad W, Andleeb S, Jalil F, Imran M, Nawaz MA, et al. Bacterial biofilm and associated infections. J Chin Med Assoc 2018; 81(1): 7-11.
  • 18. Donlan RM, Costerton JW. Biofilms: survival mechanisms of clinically relevant microorganisms. Clin Microbiol Rev 2002; 15: 167-93.
  • 19. Hoiby N, Bjarnsholt T, Moser C, Bassi GL, Coenye T, Donelli G, et al. ESCMID guideline for the diagnosis and treatment of biofilm infections 2014. Clin Microbiol Infect 2015; 21(S1): S1-S25.
There are 18 citations in total.

Details

Primary Language English
Journal Section Research Articles
Authors

Emel Mataraci Kara 0000-0003-4541-1893

Ayse Tarbin Jannuzzi This is me 0000-0003-0578-6893

Nilufer Bayrak This is me 0000-0002-0777-4012

Hatice Yildirim This is me 0000-0003-3988-6120

Mahmut Yildiz This is me 0000-0001-6317-5738

Amac Fatih Tuyu This is me 0000-0001-5698-1109

Buket Alpertunga This is me 0000-0001-6043-7560

Berna Ozbek Celik This is me 0000-0001-8909-8398

Publication Date December 6, 2019
Submission Date July 23, 2019
Published in Issue Year 2019 Volume: 78 Issue: 2

Cite

AMA Mataraci Kara E, Jannuzzi AT, Bayrak N, Yildirim H, Yildiz M, Tuyu AF, Alpertunga B, Ozbek Celik B. Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. Eur J Biol. December 2019;78(2):117-123.