Research Article

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

Volume: 78 Number: 2 December 6, 2019
  • Emel Mataraci Kara *
  • Ayse Tarbin Jannuzzi
  • Nilufer Bayrak
  • Hatice Yildirim
  • Mahmut Yildiz
  • Amac Fatih Tuyu
  • Buket Alpertunga
  • Berna Ozbek Celik
EN

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

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. 

Keywords

Supporting Institution

There are no funders to report for this submission.

References

  1. 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. 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. 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. 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. 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. 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.
  7. 8. Clinical and Laboratory Standards Institute (CLSI), Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, in, Wayne, PA, USA, 2006.
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Details

Primary Language

English

Subjects

-

Journal Section

Research Article

Publication Date

December 6, 2019

Submission Date

July 23, 2019

Acceptance Date

October 18, 2019

Published in Issue

Year 2019 Volume: 78 Number: 2

APA
Mataraci Kara, E., Jannuzzi, A. T., Bayrak, N., Yildirim, H., Yildiz, M., Tuyu, A. F., Alpertunga, B., & Ozbek Celik, 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://izlik.org/JA36DA54UM
AMA
1.Mataraci Kara E, Jannuzzi AT, Bayrak N, et al. Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. Eur J Biol. 2019;78(2):117-123. https://izlik.org/JA36DA54UM
Chicago
Mataraci Kara, Emel, Ayse Tarbin Jannuzzi, Nilufer Bayrak, et al. 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): 117-23. https://izlik.org/JA36DA54UM.
EndNote
Mataraci Kara E, Jannuzzi AT, Bayrak N, Yildirim H, Yildiz M, Tuyu AF, Alpertunga B, Ozbek Celik B (December 1, 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.
IEEE
[1]E. Mataraci Kara et al., “Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents”, Eur J Biol, vol. 78, no. 2, pp. 117–123, Dec. 2019, [Online]. Available: https://izlik.org/JA36DA54UM
ISNAD
Mataraci Kara, Emel - Jannuzzi, Ayse Tarbin - Bayrak, Nilufer - Yildirim, Hatice - Yildiz, Mahmut - Tuyu, Amac Fatih - Alpertunga, Buket - Ozbek Celik, 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 (December 1, 2019): 117-123. https://izlik.org/JA36DA54UM.
JAMA
1.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. 2019;78:117–123.
MLA
Mataraci Kara, Emel, et al. “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, Dec. 2019, pp. 117-23, https://izlik.org/JA36DA54UM.
Vancouver
1.Emel Mataraci Kara, Ayse Tarbin Jannuzzi, Nilufer Bayrak, Hatice Yildirim, Mahmut Yildiz, Amac Fatih Tuyu, Buket Alpertunga, Berna Ozbek Celik. Investigation of Antimicrobial, Antibiofilm, and Cytotoxic Effects of Straight-Chained Sulfanyl Members of Arylamino-1,4-naphthoquinones as Potential Antimicrobial Agents. Eur J Biol [Internet]. 2019 Dec. 1;78(2):117-23. Available from: https://izlik.org/JA36DA54UM