European Journal of Biology

SUBMITINFORMATION
EnglishTürkçe

Research Article


DOI :10.26650/EurJBiol.2019.0017   IUP :10.26650/EurJBiol.2019.0017    Full Text (PDF)

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

Emel Mataracı Kara, Ayşe Tarbın Jannuzzi, Nilüfer Bayrak, Hatice Yıldırım, Mahmut Yıldız, Amaç Fatih Tuyun, Buket Alpertunga, Berna Özbek Çelik

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.

Keywords: Sulfanyl 1, 4-naphthoquinone, Arylamine, Antimicrobial activity, Cytotoxicity, Biofilm

PDF View

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. google scholar
  • 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). google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 8. Clinical and Laboratory Standards Institute (CLSI), Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, in, Wayne, PA, USA, 2006. google scholar
  • 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. google scholar
  • 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. google scholar
  • 11. National Committee for Clinical Laboratory Standards. Methods for Determining Bactericidal Activity of Antimicrobial Agents- Approved Guideline M26 A. Wayne NCCLS, 1999. google scholar
  • 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. google scholar
  • 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. google scholar
  • 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. google scholar
  • 15. Nigam A, Gupta D, Sharma A. Treatment of infectious disease: Beyond antibiotics. Microbiol Res 2014; 169: 643-51. google scholar
  • 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. google scholar
  • 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. google scholar
  • 18. Donlan RM, Costerton JW. Biofilms: survival mechanisms of clinically relevant microorganisms. Clin Microbiol Rev 2002; 15: 167-93. google scholar
  • 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. google scholar

Citations

Copy and paste a formatted citation or use one of the options to export in your chosen format


EXPORT



APA

Mataracı Kara, E., Jannuzzi, A.T., Bayrak, N., Yıldırım, H., Yıldız, M., Tuyun, A.F., Alpertunga, B., & Özbek Çelik, B. (2019). Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. European Journal of Biology, 78(2), 117-123. https://doi.org/10.26650/EurJBiol.2019.0017


AMA

Mataracı Kara E, Jannuzzi A T, Bayrak N, Yıldırım H, Yıldız M, Tuyun A F, Alpertunga B, Özbek Çelik B. Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. European Journal of Biology. 2019;78(2):117-123. https://doi.org/10.26650/EurJBiol.2019.0017


ABNT

Mataracı Kara, E.; Jannuzzi, A.T.; Bayrak, N.; Yıldırım, H.; Yıldız, M.; Tuyun, A.F.; Alpertunga, B.; Özbek Çelik, B. Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. European Journal of Biology, [Publisher Location], v. 78, n. 2, p. 117-123, 2019.


Chicago: Author-Date Style

Mataracı Kara, Emel, and Ayşe Tarbın Jannuzzi and Nilüfer Bayrak and Hatice Yıldırım and Mahmut Yıldız and Amaç Fatih Tuyun and Buket Alpertunga and Berna Özbek Çelik. 2019. “Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents.” European Journal of Biology 78, no. 2: 117-123. https://doi.org/10.26650/EurJBiol.2019.0017


Chicago: Humanities Style

Mataracı Kara, Emel, and Ayşe Tarbın Jannuzzi and Nilüfer Bayrak and Hatice Yıldırım and Mahmut Yıldız and Amaç Fatih Tuyun and Buket Alpertunga and Berna Özbek Çelik. “Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents.” European Journal of Biology 78, no. 2 (Apr. 2024): 117-123. https://doi.org/10.26650/EurJBiol.2019.0017


Harvard: Australian Style

Mataracı Kara, E & Jannuzzi, AT & Bayrak, N & Yıldırım, H & Yıldız, M & Tuyun, AF & Alpertunga, B & Özbek Çelik, B 2019, 'Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents', European Journal of Biology, vol. 78, no. 2, pp. 117-123, viewed 18 Apr. 2024, https://doi.org/10.26650/EurJBiol.2019.0017


Harvard: Author-Date Style

Mataracı Kara, E. and Jannuzzi, A.T. and Bayrak, N. and Yıldırım, H. and Yıldız, M. and Tuyun, A.F. and Alpertunga, B. and Özbek Çelik, B. (2019) ‘Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents’, European Journal of Biology, 78(2), pp. 117-123. https://doi.org/10.26650/EurJBiol.2019.0017 (18 Apr. 2024).


MLA

Mataracı Kara, Emel, and Ayşe Tarbın Jannuzzi and Nilüfer Bayrak and Hatice Yıldırım and Mahmut Yıldız and Amaç Fatih Tuyun and Buket Alpertunga and Berna Özbek Çelik. “Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents.” European Journal of Biology, vol. 78, no. 2, 2019, pp. 117-123. [Database Container], https://doi.org/10.26650/EurJBiol.2019.0017


Vancouver

Mataracı Kara E, Jannuzzi AT, Bayrak N, Yıldırım H, Yıldız M, Tuyun AF, Alpertunga B, Özbek Çelik B. Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. European Journal of Biology [Internet]. 18 Apr. 2024 [cited 18 Apr. 2024];78(2):117-123. Available from: https://doi.org/10.26650/EurJBiol.2019.0017 doi: 10.26650/EurJBiol.2019.0017


ISNAD

Mataracı Kara, Emel - Jannuzzi, AyşeTarbın - Bayrak, Nilüfer - Yıldırım, Hatice - Yıldız, Mahmut - Tuyun, AmaçFatih - Alpertunga, Buket - Özbek Çelik, Berna. “Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents”. European Journal of Biology 78/2 (Apr. 2024): 117-123. https://doi.org/10.26650/EurJBiol.2019.0017



TIMELINE


Submitted23.07.2019
Accepted18.10.2019
Published Online06.12.2019

LICENCE


Attribution-NonCommercial (CC BY-NC)

This license lets others remix, tweak, and build upon your work non-commercially, and although their new works must also acknowledge you and be non-commercial, they don’t have to license their derivative works on the same terms.


SHARE




Istanbul University Press aims to contribute to the dissemination of ever growing scientific knowledge through publication of high quality scientific journals and books in accordance with the international publishing standards and ethics. Istanbul University Press follows an open access, non-commercial, scholarly publishing.