Antibacterial and Antifungal Activity of Synthesized Potassium Dithiocarbazinates: A Preliminary In Vitro Study

Document Type : Original Article

Authors

1 Associate Professor, Department of Chemistry, Faculty of Science, University of Zabol, Zabol, Iran

2 Associate Professor, Department of Biology, Faculty of Science, University of Zabol, Zabol, Iran

3 M.Sc. Student, Department of Biology, Faculty of Science, University of Zabol, Zabol, Iran

Abstract

Background:The spread of drug-resistant microbial strains has led many studies for identifying, designing, and synthesizing new antimicrobial agents.The aim of this study was to evaluate antimicrobial effects of some synthesized potassium dithiocarbazinate derivatives against 6 Gram-negative and 4 Gram-positive bacteria as well as 2 molds and 1 yeast. Potassium salts of dithiocarbazinic acids were prepared in good yields from the reaction of various hydrazides with carbon disulfide. Potassium hydroxide and diethyl ether were used as base and solvent, respectively.
Methods:Broth microdilution and streak plate methodswere applied according to the Clinical and Laboratory Standards Institute (CLSI) guidelines to determine the minimum inhibitory concentration (MIC), the minimum bactericidal concentration (MBC), and the minimum fungicidal concentration (MFC) values.
Results:Good to excellent inhibitory effects especially on fungi were observed with the tested compounds. Dithiocarbazinates 3b and 3f containing 4-nitrophenyl and 3-hydroxy-2-naphthyl substituents could effectively inhibit the growth of all tested bacterial strains. In addition, all synthesized derivatives were effective against fungal pathogens.
Conclusion:Based on the data obtained from antimicrobial susceptibility testing,designed derivatives are especially potent antifungal agents. Potassium 2-(3-hydroxy-2-naphthoyl) hydrazine-1-carbodithioate was introduced as a new wide-spectrum antimicrobial agent. Other biological activities of these water-soluble derivatives can be studied in living organisms.

Keywords


  1.  Li L, Ding H, Wang B, Yu S, Zou Y, Chai X, et al. Synthesis and evaluation of novel azoles as potent antifungal agents. Bioorg Med Chem Lett 2014; 24(1):192-4.
  2. Liu XJ, Wang L, Yin L, Cheng FC, Sun HM, Liu WW, et al. Synthesis and biological evaluation of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives as acetylcholinesterase inhibitors. J Chem Res 2017; 41(10):571-5.
  3. Li Z, Liu Y, Bai X, Deng Q, Wang J, Zhang G, et al. SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents. RSC Adv 2015; 5(118):97089-101.
  4. Seelolla G, Ponneri V. Synthesis, antimicrobial, and antioxidant activities of some fused heterocyclic [1,2,4]triazolo[3,4‐b][1,3,4]thiadiazole derivatives. J Heterocycl Chem 2016; 53(3):929-36.
  5. Gupta JK, Mishra P. Pharmacological screening of some newly synthesized triazoles for H1 receptor antagonist activity. Med Chem Res 2017; 26(10):2260-71.
  6. Wang XF, Zhang S, Li BL, Zhao JJ, Liu YM, Zhang RL, et al. Synthesis and biological evaluation of disulfides bearing 1,2,4-triazole moiety as antiproliferative agents. Med Chem Res 2017; 26(12):3367-74.
  7. Xie W, Zhang J, Ma X, Yang W, Zhou Y, Tang X, et al. Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4‐triazole as potent tyrosinase inhibitors. Chem Biol Drug Des 2015; 86(5):1087-92.
  8. Panda S, Nayak S. Antibacterial, antioxidant and anthelmintic studies of inclusion complexes of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols. Supramol Chem 2015; 27(10):679-89.
  9. Udupi RH, Suresh GV, Ramachandra Setty S, Bhat AR. Synthesis and biological evaluation of 3-substituted-4-[2'-(4''-isobutylphenyl)propionamido]-5-mercapto-1,2,4-triazoles and their derivatives. Journal of the Indian Chemical Society 2000; 77(6):302-4.
  10. Panda S, Nayak S. Studies on absorption and emission characteristics of inclusion complexes of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols. Journal of Fluorescence 2016; 26(2):413-25.
  11. Wang X, Wang H, Chen P, Pang Y, Zhao Z, Wu G. Synthesis and biological activities of some novel (E)-alpha-(methoxyimino)benzeneacetate derivatives with modified 1,2,4-triazole moiety. Journal of Chemistry 2014; 2014:681364.
  12. Bhasin G, Srivastava R, Singh R. Synthesis of triazole based novel ionic liquids and salts. Org Prep Proced Int 2017; 49(4):370-6.
  13. Mohamed FK. Synthesis, reactions and antimicrobial activity on some novel phthalazinones derivatives. Der Chemica Sinica 2010; 1(1):20-31.
  14. Aouad MR, Mayaba MM, Naqvi A, Bardaweel SK, Al-blewi FF, Messali M, et al. Design, synthesis, in silico and in vitro antimicrobial screenings of novel 1,2,4-triazoles carrying 1,2,3-triazole scaffold with lipophilic side chain tether. Chem Cent J 2017; 11:117.
  15. Yarmohammadi E, Beyzaei H, Aryan R, Moradi A. Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents. Mol Divers 2020.
  16. Liu XJ, Liu HY, Wang HX, Shi YP, Tang R, Zhang S, et al. Synthesis and antitumor evaluation of novel fused heterocyclic1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives. Med Chem Res 2019; 28(10):1718-25.
  17. Thakkar SS, Thakor P, Doshi H, Ray A. 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities. Bioorg Med Chem 2017; 25(15):4064-75.
  18. Adak AK, Leonov AP, Ding N, Thundimadathil J, Kularatne S, Low PS, et al. Bishydrazide glycoconjugates for lectin recognition and capture of bacterial pathogens. Bioconjug Chem 2010; 21(11):2065-75.
  19. Beyzaei H, Kamali Deljoo M, Aryan R, Ghasemi B, Zahedi MM, Moghaddam-Manesh M. Green multicomponent synthesis, antimicrobial and antioxidant evaluation of novel 5-amino-isoxazole-4-carbonitriles. Chem Cent J 2018; 12(1):114.
  20. Hoggarth E. 2-Benzoyldithiocarbazinic acid and related compounds. J Chem Soc 1952; 1952(0):4811-7.
  21. Centore R, Fusco S, Peluso A, Capobianco A, Stolte M, Archetti G, et al. Push–pull azo‐chromophores containing two fused pentatomic heterocycles and their nonlinear optical properties. Eur J Org Chem 2009; 2009(21):3535-43.
  22. Sonawane AD, Rode ND, Nawale L, Joshi RR, Joshi RA, Likhite AP, et al. Synthesis and biological evaluation of 1,2,4‐triazole‐3‐thione and 1,3,4‐oxadiazole‐2‐thione as antimycobacterial agents. Chem Biol Drug Des 2017; 90(2):200-9.
  23. Saha A, Kumar R, Kumar R, Devakumar C. Green synthesis of 5‐substituted‐1,3,4‐thiadiazole‐2‐thiols as new potent nitrification inhibitors. J Heterocycl Chem 2010; 47(4):838-45.
  24. Baeeri M, Foroumadi A, Motamedi M, Yahya‐Meymandi A, Firoozpour L, Ostad SN, et al. Safety and efficacy of new 3,6‐diaryl‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazine analogs as potential phosphodiesterase‐4 inhibitors in NIH‐3T3 mouse fibroblastic cells. Chem Biol Drug Des 2011; 78(3):438-44.
  25. Singh NK, Bharty MK, Kushawaha SK, Butcher RJ. Nickel (II) complexes of 5-phenyl and 5-furan-1,3,4-oxadiazole-2-thiones containing ethylenediamine: synthesis, spectral and X-ray characterization. Transition Met Chem 2010; 35(2):205-11.
  26. Singh NK, Bharty MK, Kushawaha SK, Singh UP, Tyagi P. Synthesis, spectral and structural studies of a Mn(II) complex of [N′-(pyridine-4-carbonyl)-hydrazine]-carbodithioic acid ethyl ester and Mn(II) and Ni(II) complexes of [N′-(pyridine-4-carbonyl)-hydrazine]-carbodithioic acid methyl ester. Polyhedron 2010; 29(8):1902-9.
  27. Tiperciuc B, Zaharia V, Colosi I, Moldovan C, Crişan O, Pîrnau A, et al. Synthesis and evaluation of antimicrobial activity of some new hetaryl-azoles derivatives obtained from 2-aryl-4-methylthiazol-5-carbohydrazides and isonicotinic acid hydrazide. J Heterocycl Chem 2012; 49(6):1407-14.
  28. Pandeya SN, Chattree A, Fatima I. Synthesis, antimicrobial activities and structure activity relationship of some dithiocarbazinate, 1,2,4-triazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. Der Pharma Chem 2012; 4(4):1667-73.
  29. Olender D, Żwawiak J, Zaprutko L. Multidirectional efficacy of biologically active nitro compounds included in medicines. Pharmaceuticals (Basel) 2018; 11(2):54.
  30. Wu Y, Bai J, Zhong K, Huang Y, Qi H, Jiang Y, et al. Antibacterial activity and membrane-disruptive mechanism of 3-p-trans-coumaroyl-2-hydroxyquinic acid, a novel phenolic compound from pine needles of Cedrus deodara, against Staphylococcus aureus. Molecules 2016; 21(8):1084.