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Antibacterial Activities of Coordination Compounds Containing Dicyanidoargentat (I)

Year 2020, , 115 - 122, 31.12.2020
https://doi.org/10.13002/jafag4702

Abstract

Our study is on testing of different concentrations (5, 10, 15, 20, 30 and 40 µg/ml) of twelve the newly synthesized bimetallic cyanido complexes ([Ni(hydeten)2Ag(CN)2] [Ag(CN)2].H2O (K1), [Cd2(hydeten)2Ag4(CN)8].H2O (K2), [Ni(bishydeten)2Ag(CN)2] [Ag(CN)2].H2O (K3), [Cu(bishydeten)2Ag2(CN)4] (K4), [Cd(bishydeten)0.5]2[Ag(CN)2]4.3H2O (K5), [Ni(N-bishydeten)Ag3(CN)5] (K6), [Cu(Nbishydeten)Ag3(CN)5] (K7), [Zn(N-bishydeten)Ag3(CN)5] (K8), [Cd(N-bishydeten)]4[Ag(CN)2]8[Ag(CN)]2 (K9), [Cu(edbea)Ag2(CN)4].H2O (K11), [Cd(edbea)2][Ag(CN)2]2.H2O (K12) and [Cd(edbea) Ag3(CN)5] (K13) for their antibacterial activity against Pseudomonas syringae pv. tomato (Pst), Clavibacter michiganensis subsp. michiganensis (Cmm) and Xanthomonas axonopodis pv. vesicatoria (Xav). Antibacterial activity determined using the agar well diffusion assay method.showed that compound K9 has by 90% inhibition ratio on the bacterial growth . Eight out of 12 compounds has over 90% inhibition on Cmm. Inhibitory effects varying between 72% and 100% ratio by K11 and K12 on selected bacterial strains were less than the effects of K9 and K3 which showed highly significant antibacterial activity by 93.83% and 85.71% inhibitions against Pst respectively, whereas the lowest activity was by K4 (33%) treatment at 40 µg/ml against whole bacterial pathogens tested in vitro conditions. On the other hand compound K13 exhibited the highest antibacterial activity against Xav by 99% growth inhibition at 40 µg/ml. Most of these compounds showed promising activities against the tested bacteria. Our further studies will continue on testing of their efficiency under field conditions.

References

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  • Baysal O, Gursoy YZ, Ornek H and Duru A (2005). Induction of oxidants in tomato leaves treated with dl-β-Amino butyric acid (BABA) and infected with Clavibacter michiganensis subsp. michiganensis. European Journal of Plant Pathology, 112: 361-369.
  • Boyanova L, Gergova G, Nikolov R, Derejian S, Lazarova E, Katsarov N, Mitov I and Krastev Z (2005). Activity of Bulgarian propolis against 94 Helicobacter pylori strains in vitro by agar-well diffusion, agar dilution and disc diffusion methods. Journal of Medical Microbiology, 54: 481-483.
  • Conover RA and Gerhold NR (1981) Mixture of copper and maneb or mancozeb for control of bacterial spot of tomato and their compatibility for control of fungus diseases. Proceedings of the Florida State Horticultural Society, 94: 154-156.
  • Faimali M, Sepcic K, Turk T and Geraci S (2003). Non-toxic antifouling activity of polymeric 3-alkylpyridinium salts from the Mediterranean Sponge Reniera sarai (Pulitzer-Finali). Biofouling, 19: 47-56.
  • Finney DJ (1971). Probit analysis. 3rd ed. 333 pp. Cambridge University Press.
  • Hausbeck MK, Bell J, Medina-Mora C, Podolsky R and Fulbright DW (2000). Effect of bactericides on population sizes and spread of Clavibacter michiganensis subsp. michiganensis on tomatoes in the greenhouse and on disease development and crop yield in the field. Phytopathology, 90: 38-44.
  • Hovath DM, Stall RE, Jones JB, Pauly MH, Vallad GE, Dahlbeck D, Staskawicz BJ and Scott JW (2012). Transgenic resistance confers effective field level control of bacterial spot disease in tomato. PLoS ONE 7 (8): e42036. doi:10.1371/journal.pone.0042036 .
  • Garaventa F, Faimali M, Sepcic K and Geraci S (2003). Laboratory analysis of antimicrofouling activity of poly-APS extracted from Reniera sarai (Porifera: Demospongiae). Biologia Marina Mediterranea, 10: 565-567.
  • Gleason ML, Gitaitis RD and Ricker MD (1993). Recent progress in understanding and controlling bacterial canker of tomato in eastern north America. Plant Disease, 77: 1069-1076.
  • Jones JB and Pernezny K (2003). Bacterial spot. Pages 6-7 in: Compendium of Pepper Diseases. Ed. K. Pernezny, PD. Roberts, JF. Murphy and NP. Goldberg, American Phytopathological Society, St. Paul, MN.
  • Jones JB, Zitter TA, Momol MT and Miller SA (2014) Compendium of Tomato Diseases and Pests (second ed.). Minnesota, APS Press, 25-30.
  • Jose MV, Teresa P, Adriana A, Maria G, Javier M, Margarita LT and Fernandez A (2001). The key role of sulfur in thiosemicarbazone compounds crystal and molecular structure. Journal of Organometallic Chemistry, 623: 176-184.
  • Karaca K, Yanar Y, Belguzar S, Karadag A and Korkmaz N (2020) Evaluation of antifungal activities of newly synthesized bimetallic cyanido complexes under laboratory conditions. Fresenius Environmental Bulletin, 29: 815-822.
  • Karadag A, Aydın A, Dede S, Tekin S, Yanar Y, Cadirci BH, Soylu MS and Andaç O (2015). Five novel dicyanidoaurate (I)-based complexes exhibiting significant biological activities: synthesis, characterization and three crystal structures. New Journal of Chemistry, 39: 8136-8152.
  • Karadag A, Korkmaz N, Aydın A, Tekin S, Yanar Y, Yerlif Y and Korkmaz SA (2018) In vitro biological properties and predicted DNA–BSA interaction of three new dicyanidoargentate (I)-based complexes: synthesis and characterization, New Journal of Chemistry: 42, 4679-4692.
  • King EO, Ward MK and Raney DE (1954). Two simple media for the demonstration of pyocianin and floresin. Journal of Laboratory and Clinical Mediçine, 44: 301-307.
  • Kirilmiş C, Koca M, Servi S and Gür S (2009). Synthesis and antimicrobial activity of Dinaphtho [2,1-b]furan-2-yl-methanone and their Oxime derivatives. Turkish Journal of Chemistery, 33: 374-384.
  • Korkmaz N, Karadag A, Aydın A, Yanar Y, Karaman I and Tekin S (2014). Synthesis and characterization of two novel dicyanidoargentate (I) complexes containing N-(2-hydroxyethyl) ethylenediamine exhibiting significant biological activity. New Journal of Chemistry, 38: 4760-4773.
  • Korkmaz N, Aydın A, Karadag A, Yanar Y, Maasoglu Y, Sahin E and Tekin S (2017). New bemetalic dicyanidoargentate (I)-based coordination compounds: Synthesis, characterization, biological activities and DNA-BSA binding affinities. Spectrachimica Acta Part A: Molecular and Biomolecular Spect., 173: 1007-1022.
  • Kumar VP, Chauhan NS, Padh H and Rajani MJ (2006). Search for antibacterial and antifungal agents from selected Indian medicinal plants. Journal of Ethnopharmacology, 107: 182-188.
  • Louws FJ, Wilson M, Cuppels DA, Jones JB, Shoemaker PB, Sahin F. and Miller SA (2001) Field control of bacterial spot of tomato and pepper and bacterial speck of tomato using a plant activator, Plant Disease, 85: 481-488.
  • Martin HL, Hamilton VA and Kopittke RA (2004). Copper tolerance in Australian populations of Xanthomonas campestris pv. vesicatoria contributes to poor field control of bacterial spot of pepper. Plant Disease, 88:921-924.
  • Parul N, Subhangkar N and Arun M (2012). Antimicrobial activity of different Thiosemicarbazone compounds against microbial pathogens. International Research Journal of Pharmacy, 3 (5): 350-363.
  • Pernezny K, Kudela V, Kokoskova B and Hladka I (1995). Bacterial diseases of tomato in the Czech and Slovak Republics and lack of streptomycin resistance among copper-tolerant bacterial strains. Crop Protection, 14: 267-270.
  • SPSS (2007). SPSS 16 for windows user’s guide release. Chicago Spss Inc.
  • Topliss JG, Clark AM, Ernst E, Hufford CD, Johnston GAR, Rimoldi JM and Weimann BJ (2002). Natural and synthetic substances related to human health (IUPAC Technical Report). Pure and Applied Chemistry, 74: 1957-1985.
  • Turk T, Sepcic K, Mancini I and Guella G (2008). 3-akylpyridinium and 3-alkylpyridine compounds from marine sponges, their synthesis, biological activities and potential use. In: Rahman, Atta-ur (Ed.), Studies in Natural Products Chemistry. Bioactive Natural Products (Part O), vol. 35. Elsevier, Amsterdam, pp. 355-397.
  • Werner NA, Fulbright DW, Podolsky R, Bell J and Hausbeck MK (2002). Limiting populations and spread of Clavibacter michiganensis subsp. michiganensis on seedling tomatoes in the greenhouse. Plant Disease, 86: 535-542.
  • Zovko A, Gabric MV, Sepcic K, Pohleven F, Jaklic D, Cimerman NG, Lu Z, Edrada-Ebel RA, Houssen W, Mancini I, Defant A, Jaspars M and Turk T (2012). Antifungal and antibacterial activity of 3-alkylpyridinium polymeric analogs of marine toxins. International Biodeterioration & Biodegradation, 68, 71-77.
Year 2020, , 115 - 122, 31.12.2020
https://doi.org/10.13002/jafag4702

Abstract

References

  • Andriole VTJ (1999). Current and future antifungal therapy: new targets for antifungal agents. Journal of Antimicrobial Chemotherapy, 44:151-162.
  • Baysal O, Gursoy YZ, Ornek H and Duru A (2005). Induction of oxidants in tomato leaves treated with dl-β-Amino butyric acid (BABA) and infected with Clavibacter michiganensis subsp. michiganensis. European Journal of Plant Pathology, 112: 361-369.
  • Boyanova L, Gergova G, Nikolov R, Derejian S, Lazarova E, Katsarov N, Mitov I and Krastev Z (2005). Activity of Bulgarian propolis against 94 Helicobacter pylori strains in vitro by agar-well diffusion, agar dilution and disc diffusion methods. Journal of Medical Microbiology, 54: 481-483.
  • Conover RA and Gerhold NR (1981) Mixture of copper and maneb or mancozeb for control of bacterial spot of tomato and their compatibility for control of fungus diseases. Proceedings of the Florida State Horticultural Society, 94: 154-156.
  • Faimali M, Sepcic K, Turk T and Geraci S (2003). Non-toxic antifouling activity of polymeric 3-alkylpyridinium salts from the Mediterranean Sponge Reniera sarai (Pulitzer-Finali). Biofouling, 19: 47-56.
  • Finney DJ (1971). Probit analysis. 3rd ed. 333 pp. Cambridge University Press.
  • Hausbeck MK, Bell J, Medina-Mora C, Podolsky R and Fulbright DW (2000). Effect of bactericides on population sizes and spread of Clavibacter michiganensis subsp. michiganensis on tomatoes in the greenhouse and on disease development and crop yield in the field. Phytopathology, 90: 38-44.
  • Hovath DM, Stall RE, Jones JB, Pauly MH, Vallad GE, Dahlbeck D, Staskawicz BJ and Scott JW (2012). Transgenic resistance confers effective field level control of bacterial spot disease in tomato. PLoS ONE 7 (8): e42036. doi:10.1371/journal.pone.0042036 .
  • Garaventa F, Faimali M, Sepcic K and Geraci S (2003). Laboratory analysis of antimicrofouling activity of poly-APS extracted from Reniera sarai (Porifera: Demospongiae). Biologia Marina Mediterranea, 10: 565-567.
  • Gleason ML, Gitaitis RD and Ricker MD (1993). Recent progress in understanding and controlling bacterial canker of tomato in eastern north America. Plant Disease, 77: 1069-1076.
  • Jones JB and Pernezny K (2003). Bacterial spot. Pages 6-7 in: Compendium of Pepper Diseases. Ed. K. Pernezny, PD. Roberts, JF. Murphy and NP. Goldberg, American Phytopathological Society, St. Paul, MN.
  • Jones JB, Zitter TA, Momol MT and Miller SA (2014) Compendium of Tomato Diseases and Pests (second ed.). Minnesota, APS Press, 25-30.
  • Jose MV, Teresa P, Adriana A, Maria G, Javier M, Margarita LT and Fernandez A (2001). The key role of sulfur in thiosemicarbazone compounds crystal and molecular structure. Journal of Organometallic Chemistry, 623: 176-184.
  • Karaca K, Yanar Y, Belguzar S, Karadag A and Korkmaz N (2020) Evaluation of antifungal activities of newly synthesized bimetallic cyanido complexes under laboratory conditions. Fresenius Environmental Bulletin, 29: 815-822.
  • Karadag A, Aydın A, Dede S, Tekin S, Yanar Y, Cadirci BH, Soylu MS and Andaç O (2015). Five novel dicyanidoaurate (I)-based complexes exhibiting significant biological activities: synthesis, characterization and three crystal structures. New Journal of Chemistry, 39: 8136-8152.
  • Karadag A, Korkmaz N, Aydın A, Tekin S, Yanar Y, Yerlif Y and Korkmaz SA (2018) In vitro biological properties and predicted DNA–BSA interaction of three new dicyanidoargentate (I)-based complexes: synthesis and characterization, New Journal of Chemistry: 42, 4679-4692.
  • King EO, Ward MK and Raney DE (1954). Two simple media for the demonstration of pyocianin and floresin. Journal of Laboratory and Clinical Mediçine, 44: 301-307.
  • Kirilmiş C, Koca M, Servi S and Gür S (2009). Synthesis and antimicrobial activity of Dinaphtho [2,1-b]furan-2-yl-methanone and their Oxime derivatives. Turkish Journal of Chemistery, 33: 374-384.
  • Korkmaz N, Karadag A, Aydın A, Yanar Y, Karaman I and Tekin S (2014). Synthesis and characterization of two novel dicyanidoargentate (I) complexes containing N-(2-hydroxyethyl) ethylenediamine exhibiting significant biological activity. New Journal of Chemistry, 38: 4760-4773.
  • Korkmaz N, Aydın A, Karadag A, Yanar Y, Maasoglu Y, Sahin E and Tekin S (2017). New bemetalic dicyanidoargentate (I)-based coordination compounds: Synthesis, characterization, biological activities and DNA-BSA binding affinities. Spectrachimica Acta Part A: Molecular and Biomolecular Spect., 173: 1007-1022.
  • Kumar VP, Chauhan NS, Padh H and Rajani MJ (2006). Search for antibacterial and antifungal agents from selected Indian medicinal plants. Journal of Ethnopharmacology, 107: 182-188.
  • Louws FJ, Wilson M, Cuppels DA, Jones JB, Shoemaker PB, Sahin F. and Miller SA (2001) Field control of bacterial spot of tomato and pepper and bacterial speck of tomato using a plant activator, Plant Disease, 85: 481-488.
  • Martin HL, Hamilton VA and Kopittke RA (2004). Copper tolerance in Australian populations of Xanthomonas campestris pv. vesicatoria contributes to poor field control of bacterial spot of pepper. Plant Disease, 88:921-924.
  • Parul N, Subhangkar N and Arun M (2012). Antimicrobial activity of different Thiosemicarbazone compounds against microbial pathogens. International Research Journal of Pharmacy, 3 (5): 350-363.
  • Pernezny K, Kudela V, Kokoskova B and Hladka I (1995). Bacterial diseases of tomato in the Czech and Slovak Republics and lack of streptomycin resistance among copper-tolerant bacterial strains. Crop Protection, 14: 267-270.
  • SPSS (2007). SPSS 16 for windows user’s guide release. Chicago Spss Inc.
  • Topliss JG, Clark AM, Ernst E, Hufford CD, Johnston GAR, Rimoldi JM and Weimann BJ (2002). Natural and synthetic substances related to human health (IUPAC Technical Report). Pure and Applied Chemistry, 74: 1957-1985.
  • Turk T, Sepcic K, Mancini I and Guella G (2008). 3-akylpyridinium and 3-alkylpyridine compounds from marine sponges, their synthesis, biological activities and potential use. In: Rahman, Atta-ur (Ed.), Studies in Natural Products Chemistry. Bioactive Natural Products (Part O), vol. 35. Elsevier, Amsterdam, pp. 355-397.
  • Werner NA, Fulbright DW, Podolsky R, Bell J and Hausbeck MK (2002). Limiting populations and spread of Clavibacter michiganensis subsp. michiganensis on seedling tomatoes in the greenhouse. Plant Disease, 86: 535-542.
  • Zovko A, Gabric MV, Sepcic K, Pohleven F, Jaklic D, Cimerman NG, Lu Z, Edrada-Ebel RA, Houssen W, Mancini I, Defant A, Jaspars M and Turk T (2012). Antifungal and antibacterial activity of 3-alkylpyridinium polymeric analogs of marine toxins. International Biodeterioration & Biodegradation, 68, 71-77.
There are 30 citations in total.

Details

Primary Language English
Journal Section Research Articles
Authors

Kübra Karaca This is me

Sabriye Belgüzar This is me

Yusuf Yanar This is me

Ahmet Karadag This is me

Nesrin Korkmaz This is me

Publication Date December 31, 2020
Published in Issue Year 2020

Cite

APA Karaca, K., Belgüzar, S., Yanar, Y., Karadag, A., et al. (2020). Antibacterial Activities of Coordination Compounds Containing Dicyanidoargentat (I). Journal of Agricultural Faculty of Gaziosmanpaşa University (JAFAG), 37(3), 115-122. https://doi.org/10.13002/jafag4702