Antimicrobial Activities of Naphthalenylmethylen Hydrazine Derivatives

Öz

In clinical microbiology and antibacterial research, the significance of drug-resistant pathogens is growing up. Hydrazine-type compounds constitute the main classes of chemicals for the investigation of multidrug resistant agents which causes microbial infections. In the current study antimicrobial activities of certain Naphthalenylmethylen Hydrazine derivatives were examined to appraise their efficacy. The effectiveness of new compounds were evaluated using 2-fold serial dilutions against Staphylococcus aureus, Methicillin-Resistant-Staphylococcus aureus (MRSA), Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, and Candida albicans. Minimum inhibitory concentration (MIC) was determined for test compounds and for the reference standards Ciprofloxacin, ampicillin, and miconazole. According to the results, although the new compounds demonstrated poor antibacterial effects in general, the 1e and 1h compounds showed off significant antibacterial effects, especially against MRSA strains.

Anahtar Kelimeler

• Antimicrobial
• Hydrazine
• Indole
• MRSA
• Naphthalene

Destekleyen Kurum

Scientific Research Council of Erzincan Binali Yildirim University

Proje Numarası

SAG-A-240215-0120

Teşekkür

Author appreciate Prof. Dr. Nurten Altanlar for perform antibacterial activity tests.

Naftalenilmetilen Hidrazin Türevlerinin Antimikrobiyal Aktiviteleri

Öz

Klinik mikrobiyoloji ve antibakteriyal araştırmalarda, ilaca dirençli patojenlerin önemi artmaktadır. Hidrazin tipi bileşikler, mikrobiyal enfeksiyonlarda çoklu ilaca dirençli ajanların araştırılması için önemli bir kimyasal sınıf olarak bilinmektedir. Bu çalışmada, belirli Naftalenilmetilen Hidrazin türevlerinin antimikrobiyal aktiviteleri incelenerek bu bileşiklerin etkinlikleri değerlendirilmiştir. Test edilen bileşiklerin antimikrobiyal etkinlikleri, 2-kat seri dilüsyon yöntemi kullanılarak, Staphylococcus aureus, Methicillin-Resistant-Staphylococcus aureus (MRSA), Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli ve Candida albicans’a karşı araştırılarak değerlendirilmiştir. Test edilen bileşiklerin Minimum İnhibisyon Konsantrasyonu (MİK), siprofloksasin, ampisilin ve mikonazol gibi standart referans bileşiklere karşı belirlenmiştir. Aktivite sonuçlarına göre, bileşikler genel olarak zayıf antibakteriyal etki göstermelerine rağmen, 1e ve 1h bileşikleri özellikle MRSA suşlarına karşı önemli antibakteriyal etki göstermişlerdir.

Anahtar Kelimeler

• antimikrobiyal
• hidrazin
• indol
• MRSA
• Naftalen

Proje Numarası

SAG-A-240215-0120

Kaynakça

1. Abdel-Fattah, M.E., Salem, E., Mahmoud, M.A. (2000). ‘’Synthesis and antimicrobial activity of some 3-p-chlorophenoxymethyl-4-phenyl-1,2,4-triazol-5-ylthio- acetyl hydrazine derivatives’’, Indian J. Heterocycl. Chem, 10, 121-128.
2. Bektas, H., Demirbas, A., Demirbas, N., Karaoglu, S.A. (2010). ‘’Synthesis of some new biheterocyclic triazole derivatives and evaluation of their antimicrobial activity’’, Turk. J. Chem, 34, 165-180.
3. Blair, J.M., Webber, M.A., Baylay, A.J., Ogbolu, D.O., Piddock, L.J. (2015). ‘’Molecular mechanisms of antibiotic resistance’’, Nat. Rev. Microbiol, 13(1), 42–51.
4. Clinical and Laboratory Institute. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, Approved Standard. in: CLSI Publication M07-A10, Twelfth ed. CLSI; Wayne, PA,USA; 2009.
5. Clinical and Laboratory Standards Institute (CLSI), Reference method for broth dilution antifungal susceptbility testing of yeasts; Approved Standart. Third ed. CLSI document M27-A3. Wayne, PA, USA; 2008.
6. Gordon, R.J., Lowy, F.D. (2008). ‘’Pathogenesis of methicillin-resistant Staphylococcus aureus infection’’, Clin. Infect. Dis, 350–359.
7. Karali, N., Gursoy, A., Kandemirli, F., Shvets, N., Kaynak, F. B., Ozbey, S., Kovalishyn, V., Dimogloc, A. (2007). ‘’Synthesis and structure-antituberculosis activity relationship of 1H-indole-2,3-dione derivatives’’, Bioorg. Med. Chem, 15, 5888-5904.
8. Kidwai, M., Negi, N., Gupta, S.D. (1994). ‘’Synthesis and antifertility activity of 1,5-diaryl-3 (3 indolyl) formazans’’, Chem Pharm Bull, 42(11), 2363-2364.

9. Kumar, P., Narasimhan, B. (2013). ‘’Hydrazides/hydrazones as antimicrobial and anticancer agents in the new millennium’’, Mini Rev Med Chem, 13(7), 971-87.
10. Loncle, C., Brunel, J.M., Vidal, N., Dherbomez, M., Letourneux, Y. (2004). ‘’Synthesis and antifungal activity of cholesterol-hydrazone derivatives’’, Eur. J. Med. Chem, 39, 1067-1071.
11. Maccari, R., Ottana, R., Vigorita, M.G. (2005). ‘’In vitro advanced antimycobacterial screening of isoniazid-related hydrazones, hydrazides and cyanoboranes Part 14’’, Bioorg. Med. Chem. Lett, 15, 2509-2513.
12. Madabhavi, I., Sarkar, M., Kadakol, N. (2020). ‘’COVID-19: a review’’, Monaldi Arch Chest Dis, 90(2). doi: 10.4081/monaldi.2020.1298.
13. Nastasa, D.C., Ionuţ, I., Stana, A., Benedec, D., Tamaian, R., Oniga, O., Tiperciuc, B. (2018). ‘’Antibacterial Evaluation and Virtual Screening of New Thiazolyl-Triazole Schiff Bases as Potential DNA-Gyrase Inhibitors’’, Int J Mol Sci, 19(1), 222. doi: 10.3390/ijms19010222.
14. Okwu, M.U., Olley, M., Akpoka, A.O., Izevbuwa, O.E. (2019). ‘’Methicillin-resistant Staphylococcus aureus (MRSA) and anti-MRSA activities of extracts of some medicinal plants: A brief review’’, AIMS Microbiol, 5(2), 117-137.
15. Puskullu, M.O., Celik, I., Erol, M., Fatullayev, H., Uzunhisarcikli, E., Kuyucuklu, G. (2020). ‘’Antimicrobial and antiproliferative activity studies of some new quinoline- 3-carbaldehyde hydrazone derivatives’’, Bioorganic Chemistry, 101, 104014.
16. Shirinzadeh, H., Suzen, S., Altanlar, N., Westwell, D.A. (2018). ‘’Antimicrobial Activities of New Indole Derivatives Containing 1,2,4-Triazole, 1,3,4-Thiadiazole and Carbothioamide’’, Turk J Pharm Sci, 15(3), 291-297.
17. Shirinzadeh, H., Altanlar, N., Yucel, N., Ozden, S., Suzen, S. (2011). ‘’Antimicrobial Evaluation of Indole-Containing Hydrazone Derivatives’’, Z. Naturforsch, 66c, 340-344.
18. Shirinzadeh, H., Dilek, E. (2020). ‘’Synthesis, characterization and biological activity evaluation of novel naphthalenylmethylen hydrazine derivatives as carbonic anhydrase inhibitors’’, Journal of Molecular Structure, 128657.
19. Shirinzadeh, H., Eren, B., Gurer-Orhan, H., Suzen, S., Ozden, S. (2010). ‘’Novel indole-based analogs of melatonin: Synthesis and in vitro antioxidant activity studies’’, Molecules, 15, 2187-2202.
20. Shirinzadeh, H., Ghalia, M., Tascioglu, A., Adjali, F.I., Gunesacar, G., Gurer-Orhan, H., Suzen, S. (2020). ‘’Bioisosteric modification on melatonin: synthesis of new naphthalene derivatives, in vitro antioxidant activity and cytotoxicity studies’’, Braz. J. Pharm. Sci, 56, 18124.
21. Spagnuolo, G., De Vito, D., Rengo, S., Tatullo, M. (2020). ‘’COVID-19 Outbreak: An Overview on Dentistry’’, Int J Environ Res Public Health, 17(6), 2094. doi: 10.3390/ijerph17062094.
22. Sridhar, S.K., Pandeya, S.N., Stables, J.P., Ramesh, A. (2002). ‘’Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives’’, Eur. J. Pharm. Sci, 16, 129-132.
23. Suriyati, M., Pazilah, I., Habibah, A.W. (2007). ‘’Effects of isoniazid on viability, cell morphologies and acid fastness properties of Mycobacterium avium NCTC 8559 during the growth cycle’’, Chemotherapy, 53, 263-266.
24. Taşci, M., Temiz-Arpaci, O., Kaynak-Onurdag, F., Okten, S. (2018). ‘’Synthesis and antimicrobial evaluation of novel 5-substituted-2-(p-tert-butylphenyl) benzoxazoles’’, Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 385-389.