Advances in nano research

  • 제10권4호
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  • Pages.373-383
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  • 2021
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  • 2287-237X(pISSN)
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  • 2287-2388(eISSN)
테크노프레스 (Techno-Press)
권호 표지
DOI QR코드

DOI QR Code

Silver (I)- Schiff-base complex intercalated layered double hydroxide with antimicrobial activity

  • Barnabas, Mary Jenisha (Department of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University) ;
  • Parambadath, Surendran (Department of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University) ;
  • Nagappan, Saravanan (Department of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University) ;
  • Chung, Ildoo (Department of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University) ;
  • Ha, Chang-Sik (Department of Polymer Science and Engineering, School of Chemical Engineering, Pusan National University)
  • 투고 : 2018.12.26
  • 심사 : 2021.01.02
  • 발행 : 2021.04.25
⟨ 이전 논문 다음 논문 ⟩

초록

In this work, silver nitrate complexes of sulfanilamide-5-methyl-2-thiophene carboxaldehyde (SMTCA) ligand intercalated Zn/Al-layered double hydroxide [Ag-SMTCA-LDH] were synthesized for the potential application as an antimicrobial system. The SMTCA ligand was synthesized by reacting sulfanilamide and 5-methyl-2-thiophene carboxaldehyde in methanol and further complexation with silver nitrate metal ions [Ag-SMTCA]. The structural analyses of synthesized compounds confirmed an intercalation of Ag-SMTCA into Zn/Al-NO3-LDH by flake/restacking method. SMTCA, Ag-SMTCA and Ag-SMTCA-LDH were characterized by 1H nuclear magnetic resonance (1H NMR) spectroscopy, Fourier-transform infrared (FTIR), ultraviolet-visible (UV-Vis) spectrophotometer, scanning electron microscopy (SEM) and transmission electron microscopy (TEM), X-ray diffraction (XRD), and thermogravimetric analysis (TGA). It was found that Ag-SMTCA-LDH exhibited good antimicrobial activity against both gram-positive (Bacillus subtilis, [B. subtilis], Staphylococcus aures, [S. aureus]) and gram-negative (Escherichia coli, [E. coli], Pseudomonas aeruginosa [P. aeroginosa]) bacteria as well as excellent antioxidant activity.

키워드

과제정보

The work was supported by the National Research Foundation of Korea (NRF) Grant funded by the Ministry of Science and ICT, Korea {NRF-2017R1A2B3012961) and Brain Korea 21 Plus Program (4199990414196)).

참고문헌

  1. Abderrazek, K., Najoua, F.S. and Srasra, E. (2016), "Synthesis and characterization of [Zn-Al] LDH: Study of the effect of calcination on the photocatalytic activity", Appl. Clay Sci., 119, 229-235. https://doi.org/10.1016/j.clay.2015.10.014
  2. Ahmadi, R.A. and Amani, S. (2012), "Synthesis, spectroscopy, thermal analysis, magnetic properties and biological activity studies of Cu(II) and Co(II) complexes with Schiff base dye ligands", Molecules, 17, 6434-6448. https://doi.org/10.3390/molecules17066434
  3. Barbosa, C.A.S., Ferreira A.M.D.C. and Constantino, V.R.L. (2002), "Preparation and characterization of Cu (II) phthalocyanine tetrasulfonate intercalated and supported on layered double hydroxides", J. Incl. Phenom. Macrocycl. Chem., 42, 15-23. https://doi.org/10.1023/A:1014598231722
  4. Barnabas, M.J., Parambadath, S. and Ha, C.S. (2017), "Amino modified core-shell mesoporous silica based layered double hydroxide (MS-LDH) for drug delivery", J. Ind. Eng. Chem., 53, 392-403. https://doi.org/10.1016/j.jiec.2017.05.011
  5. Buey, J., Coco, S., Diez, L., Espinet, P., Alvarez, J.M.M. and Miguel, J.A. (1998), "Synthesis and second-order nonlinear optical properties of new palladium(II) and platinum(II) schiff base complexes", Organometallics, 17, 1750-1755. https://doi.org/10.1021/om9708900
  6. Caboni, P., Sarais, G., Aissani, N., Tocco, G., Sasanelli, N., Liori, B., Carta, A. and Angioni, A. (2012), "Nematicidal activity of 2 thiophenecarboxaldehyde and methylisothiocyanate from caper (Capparis spinosa) against meloidogyne incognita", J. Agric. Food Chem., 60, 7345-7351. https://doi.org/10.1021/jf302075w
  7. Cohen, S.M., Fukushima, S., Gooderham, N.J., Guengerich, F.P., Hecht, S.S., Rietjens, I.M., Smith, R.L., Bastaki, M., Harman, C.L., McGowen, M.M. and Valerio, L.G. (2017), "Safety evaluation of substituted thiophenes used as flavoring ingredients", Food Chem. Toxicol., 99, 40-50. https://doi.org/10.1016/j.fct.2016.10.023
  8. Delahaye, E., Eyele-Mezui, S., Diop, M., Leuvrey, C., Rabu, P. and Rogez, G. (2010), "Rational synthesis of chiral layered magnets by functionalization of metal simple hydroxides with chiral and non-chiral Ni(II) Schiff base complexes", Dalton Trans., 39, 10577-10580. https://doi.org/10.1039/C0DT00834F
  9. Dibrov, P., Dzioba, J., Gosink, K.K. and Hase, C.C. (2002), "Chemiosmoticmechanism of antimicrobial activity of Ag in Vibrio cholera", Antimicrob. Agents Chemother., 46, 2668-2670. https://doi.org/10.1128/AAC.46.8.2668-2670.2002
  10. Ding, X., Yuan, P., Gao, N., Zhu, H., Yang, Y.Y. and Xu, Q.H. (2017), "Au-Ag core-shell nanoparticles for simultaneous bacterial imaging and synergistic antibacterial activity", Nanomed.-Nanotechnol., 13, 297-305. https://doi.org/10.1016/j.nano.2016.09.003
  11. Feng, Y., Jiang, Y., Huang, Q., Chen, S., Zhang, F., Tang, P. and Li, D. (2014), "High antioxidative performance of layered double hydroxides/polypropyelene composite with intercalation of low-molecular weight phenolic antioxidant", Ind. Eng. Chem. Res., 53, 2287-2292. https://doi.org/10.1021/ie403643v
  12. Ganesh, M., Aziz, A.S., Ubaidaulla, U., Hemalatha, P., Saravanakumar, A., Ravikumar, R., Peng, M.M., Choi, E.Y. and Jang, H.T. (2016), "Sulfanilamide and silver nanoparticles-loaded polyvinyl alcohol-chitosan composite electrospun nanofibers: Synthesis and evaluation on synergism in wound healing", J. Ind. Eng. Chem., 39, 127-135. https://doi.org/10.1016/j.jiec.2016.05.021
  13. Goss, C.H.A., Henderson, W., Wilkins, A.L. and Evans, C. (2003), "Synthesis, characterization and biological activity of gold(III) catecholate and related complexes", J. Organomet. Chem., 679, 194-201. https://doi.org/10.1016/S0022-328X(03)00585-0
  14. Harinath, Y., Reddy, D.H.K., Kumar, B.N., Apparao, Ch. and Seshaiah, K. (2013), "Synthesis, spectral characterization and antioxidant activity studies of a bidentate Schiff base, 5-methyl thiophene-2-carboxaldehyde-carbohydrazone and its Cd(II), Cu(II), Ni(II) and Zn(II) complexes", Spectrochim. Acta. Part A Mol. Biomol. Spectros., 101, 264-272. https://doi.org/10.1016/j.saa.2012.09.085
  15. Ingale, V.D., Shinde, V.G., Dighore, N.R., Rajbhoj, A.S. and Gaikwad, S.T. (2015), "Synthesis, characterization and antimicrobial activity of a bivalent schiff base derived from salicylaldehyde and 4-methoxyaniline and its lanthanides (III) complexes", J. Chem. Pharm. Res., 7, 493-499.
  16. Isa, I.M., Sohaimi, N.M., Hashim, N., Kamari, A., Mohamed, A., Ahmad, M. and Ghani, S.A. (2013), "Determination of salicylate ion by potentiometric membrane electrode based on zinc aluminium layered double hydroxides-4(2,4-dichlorophenoxy) butyrate nanocomposites", Int. J. Electrochem. Sci., 8, 2112-2121.
  17. Jamuna, K., Naik, B.R., Sreenu, B. and Seshaiah, K. (2012), "Synthesis, characterization and antibacterial activity of Cu(II) and Fe(III) complexes of a new tridentate Schiff base ligand", J. Chem. Pharm. Res., 4(9), 4275-4282.
  18. Ji, T., Chen, L., Schmitz, M., Bao, F.S. and Zhu, J. (2015), "Hierarchical macrotube/mesopore carbon decorated with mono-dispersed Ag nanoparticles as a highly active catalyst", Green Chem., 17, 2515-2523. https://doi.org/10.1039/C5GC00123D
  19. Keshk, S.M., Ramadan, A.M., Al-Sehemi, A.G. and Bondock, S. (2016), "Peculiar behavior of starch 2,3-dialdehyde towards sulfanilamide and sulfathiazole", Carbohyd. Polym., 152, 624-631. https://doi.org/10.1016/j.carbpol.2016.07.061
  20. Khanye, S.D., Wan, B., Franzblau, S.G., Gut, J., Rosenthal, P.J., Smith, G.S. and Chibale, K. (2011), "Synthesis and in vitro antimalarial and antitubercular activity of gold(III) complexes containing thiosemicarbazone ligands", J. Organomet. Chem., 696, 3392-3396. https://doi.org/10.1016/j.jorganchem.2011.07.026
  21. Khoo, T.J., bin Break, M.K., Crouse, K.A., Tahir, M.I.M., Ali, A.M., Cowley, A.R., Watkin, D.J. and Tarafder, M.T.H. (2014), "Synthesis, characterization and biological activity of two Schiff base ligands and their nickel(II), copper(II), zinc(II) and cadmium(II) complexes derived from S-4-picolyldithiocarbazate and X-ray crystal structure of cadmium(II) complex derived from pyridine-2-carboxaldehyde", Inorg. Chim. Acta., 413, 68-76. https://doi.org/10.1016/j.ica.2014.01.001
  22. Kong, X., Jin, L., Wei, M. and Duan, X. (2010), "Antioxidant drugs intercalated into layered double hydroxide: Structure and in vitro release", Appl. Clay Sci., 49, 324-329. https://doi.org/10.1016/j.clay.2010.06.017
  23. Kursunlu, A.N., Guler, E., Dumrul, H., Kocyigit, O. and Gubbuk, I.H. (2009), "Chemical modification of silica gel with synthesized new Schiff base derivatives and sorption studies of cobalt (II) and nickel (II)", Appl. Surf. Sci., 255, 8798-8803. https://doi.org/10.1016/j.apsusc.2009.06.055
  24. Lacikova, L., Jancova, M., Muselik, J., Masterova, I., Grancai, D. and Fickova, M. (2009), "Antiproliferative, cytotoxic, antioxidant activity and polyphenols contents in leaves of four Staphylea L. species", Molecules, 14, 3259-3267. https://doi.org/10.3390/molecules14093259
  25. Lonkar, S.P., Kutlu, B., Leuteritz, A. and Heinrich, G. (2013a), "Nanohybrids of phenolic antioxidant intercalated into Mg-Al-layered double hydroxide clay", Appl. Clay Sci., 71, 8-14. https://doi.org/10.1016/j.clay.2012.10.009
  26. Lonkar, S.P., Leuteritz, A. and Heinrich, G. (2013b), "Antioxidant intercalated layered double hydroxides: a new multifunctional nanofiller for polymers", RSC Adv., 3, 1495-1501. https://doi.org/10.1039/C2RA21956E
  27. Marcato, P.D., Parizotto, N.V., Martinez, D.S.T., Paula, A.J., Ferreira, I.R., Melo, P.S., Duran, N. and Alves, O.L. (2013), "New hybrid material nased on layered double hydroxides and biogenic silver nanoparticles: antimicrobial activity and cytotoxic effect", J. Braz. Chem. Soc., 24, 266-272. http://dx.doi.org/10.5935/0103-5053.20130034
  28. Mishra, G., Dash, B., Pandey, S. and Mohanty, P.P. (2013), "Antibacterial actions of silver nanoparticles incorporated Zn-Al layered double hydroxide and its spinel", J. Environ. Chem. Eng., 1, 1124-1130. https://doi.org/10.1016/j.jece.2013.08.031
  29. Nocchetti, M., Donnadio, A., Ambrogi, V., Andreani, P., Bastianini, M., Pietrella, D. and Latterini, L. (2013), "Ag/AgCl nanoparticle decorated layered double hydroxides: synthesis, characterization and antimicrobial properties", J. Mater. Chem. B, 1, 2383-2393. https://doi.org/10.1039/C3TB00561E
  30. Noh, W., Sun, X., Ramachandran, A., Rearick, C. and Dey, S.K. (2012), "Synthesis and characterization of silver (core)/layered double hydroxide (shell) nanoparticles", Int. J. Mater. Sci., 2(3), 83-87.
  31. Nunes, J.H.B., de Paiva, R.E.F., Cuin, A., Lustri, W.R. and Corbi, P.P. (2015), "Silver complexes with sulfathiazole and sulfamethoxazole: Synthesis, spectroscopic characterization, crystal structure and antibacterial assays", Polyhedron, 85, 437-444. https://doi.org/10.1016/j.poly.2014.09.010
  32. Ozbek, N., Alyar, S., Memmi, B.K., Gunduzalp, A.B., Bahceci, Z. and Alyar, H. (2017), "Synthesis, characterization, computational studies, antimicrobial activities and carbonic anhydrase inhibitor effects of 2-hydroxy acetophenone-N-methyl p-toluenesulfonylhydrazone and its Co(II), Pd(II), Pt(II) complexes", J. Mol. Struct., 1127, 437-448. https://doi.org/10.1016/j.molstruc.2016.07.122
  33. Pan, Y., Wang, K., Huang, S., Wang, H., Mu, X., He, C., Ji, X., Zhang, J. and Huang, F. (2008), "Antioxidant activity of microwave-assisted extract of longan (Dimocarpus Longan Lour.) peel", Food Chem., 106, 1264-1270. https://doi.org/10.1016/j.foodchem.2007.07.033
  34. Parida, K.M., Sahoo, M. and Singha, S. (2016), "A novel approach towards solvent-free epoxidation of cyclohexene by Ti(IV)-Schiff base complex-intercalated LDH using H2O2 as oxidant", J. Catal., 276, 161-169. https://doi.org/10.1016/j.jcat.2010.09.012
  35. Peng, F., Wang, D., Zhang, D., Yan, B., Cao, H., Qiao, Y. and Liu, X. (2018), "PEO/Mg-Zn-Al LDH composite coating on Mg alloy as a Zn/Mg ion-release platform with multifunctions: enhanced corrosion resistance, osteogenic, and antibacterial activities", ACS Biomater. Sci. Eng., 4(12), 4112-4121. https://doi.org/10.1021/acsbiomaterials.8b01184
  36. Prabhu, S. and Poulose, E.K. (2012), "Silver nanoparticles: mechanism of antimicrobial action, synthesis, medical applications, and toxicity effects", Int. Nano Lett., 2(1), article no. 32. https://doi.org/10.1186/2228-5326-2-32
  37. Ran, X., Wang, L., Cao, D. Lin, Y. and Hao, J. (2011), "Synthesis, characterization and in vitro biological activity of cobalt(II), copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and D,L-selenomethionine", Appl. Organomet. Chem., 25(1), 9-15. https://doi.org/10.1002/aoc.1680
  38. Rani, M. and Mohamad, Y. (2014), "Synthesis, studies and in vitro antibacterial activity of some 5-(thiophene-2-yl)-phenyl pyrazoline derivatives", J. Saudi Chem. Soc., 18, 411-417. https://doi.org/10.1016/j.jscs.2011.09.002
  39. Ray, S., Mohan, R., Singh, J.K., Samantaray, M.K., Shaikh, M.M., Panda, D. and Ghosh, P. (2007), "Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver n-heterocyclic carbene complexes", J. Am. Chem. Soc., 129, 15042-15053. https://doi.org/10.1021/ja075889z
  40. Rasouli, N., Movahedi, M. and Doudi, M. (2017), "Synthesis and characterization of inorganic mixed metal oxide nanoparticles derived from Zn-Al layered double hydroxide and their antibacterial activity", Surf. Interf., 6, 110-115. https://doi.org/10.1016/j.surfin.2016.11.007
  41. Rubino, S., Busa, R., Attanzio, A., Alduina, R., Di Stefano, V., Girasolo, M.A., Orecchio, S. and Tesoriere, L. (2017), "Synthesis, properties, antitumor and antibacterial activity of new Pt(II) and Pd(II) complexes with 2,20 - dithiobis(benzothiazole) ligand", Bioorgan. Med. Chem., 25, 2378-2386. https://doi.org/10.1016/j.bmc.2017.02.067
  42. Salehi, M., Ghasemi, F., Kubicki, M., Asadi, A., Behzad, M., Ghasemi, M.H. and Gholizadeh, A. (2016), "Synthesis, characterization, structural study and antibacterial activity of the Schiff bases derived from sulfanilamides and related copper(II) complexes", Inorg. Chim. Acta., 453, 238-246. https://doi.org/10.1016/j.ica.2016.07.028
  43. Savic, N.D., Milivojevic, D.R., Glisic, B.D., Ilic-Tomic, T., Veselinovic, J., Pavic, A., Vasiljevic, B., Nikodinovic-Runic, J. and Djuran, M.I. (2016), "A comparative antimicrobial and toxicological study of gold(III) and silver(I) complexes with aromatic nitrogen-containing heterocycles: synergistic activity and improved selectivity index of Au(III)/Ag(I) complexes mixture", RSC Adv., 6, 13193-13206. https://doi.org/10.1039/C5RA26002G
  44. Sharaby, C.M. (2007), "Synthesis, spectroscopic, thermal and antimicrobial studies of some novel metal complexes of Schiff base derived from [N1-(4-methoxy-1,2,5-thiadiazol-3-yl)sulfanilamide] and 2-thiophene carboxaldehyde", Spectrochim. Acta. Part A Mol. Biomol. Spectros., 66, 1271-1278. https://doi.org/10.1016/j.saa.2006.05.030
  45. Shebl, M., Khalil, S.M.E., Ahmed, S.A. and Medien, H.A.A. (2010), "Synthesis, spectroscopic characterization and antimicrobial activity of mono-, bi- and tri-nuclear metal complexes of a new Schiff base ligand", J. Mol. Struct., 980, 39-50. https://doi.org/10.1016/j.molstruc.2010.06.034
  46. Shi, H., Yu, C. and He, J. (2010), "On the structure of layered double hydroxides intercalated with titanium tartrate complex for catalytic asymmetric sulfoxidation", J. Phys. Chem. C, 114, 17819-17828. https://doi.org/10.1021/jp106931g
  47. Sondi, I. and Salopek-Sondi, B. (2004), "Silver nanoparticles as antimicrobial agent: a case study on E. coli as a model for Gram-negative bacteria", J. Colloid Interf. Sci., 275, 177-182. https://doi.org/10.1016/j.jcis.2004.02.012
  48. Tenreiro, S., Alberdi, G., Martinez, J., Lopez-Torres, M., Ortigueira, J.M., Pereira, M.T. and Vila, J.M. (2003), "New palladium(II) cyclometallated compounds derived from transcinnamalylideneimines via C-H activation of an sp2 - aliphatic carbon atom", Inorg. Chim. Acta, 342, 145-150. https://doi.org/10.1016/S0020-1693(02)01156-8
  49. Uddin, M.N., Chowdhury, D.A., Rony, M.M. and Halim, M.E. (2014), "Metal complexes of Schiff bases derived from 2-thiophenecarboxaldehyde and mono/diamine as the antibacterial agents", Modern Chem., 2(2), 6-14. https://doi.org/10.11648/j.mc.20140202.11
  50. Ukrainczyk, L., Chibwe, M., Pinnavaia, T.J. and Boyd, S.A. (1994), "ESR study of cobalt(II) tetratis(N-methyl-4-pyridmiumyl)porphyrin and cobalt(II) tetrasulfophthalocyanine intercalated in layered aluminosilicates and a layered double hydroxide", J. Phys. Chem., 98(10), 2668-2676. https://doi.org/10.1021/j100061a026
  51. Vanja, M. and Gurusamy, A. (2013), "Coleus aromaticus leaf extract mediated synthesis of silver nanoparticles and its bacterial activity", Appl. Nanosci., 3, 217-223. https://doi.org/10.1007/s13204-012-0121-9
  52. Wang, Y. and Zhang, D. (2012), "Synthesis, characterization, and controlled release antibacterial behavior of antibiotic intercalated Mg-Al layered double hydroxides", Mater. Res. Bull., 47, 3185-3194. https://doi.org/10.1016/j.materresbull.2012.08.029
  53. Wang, M.Z., Li, Y., Ji, J.J., Huang, G.L., Zhang, X., Li, S.H. and Yang, X.J. (2013), "Novel hybrids of Cu2+ ternary complexes of salicylidene-amino acid Schiff base with phenanthroline (or bipyridine) intercalated in Mg/Al-NO3-layered double hydroxide", Chinese Chem. Lett., 24, 593-596. https://doi.org/10.1016/j.cclet.2013.03.040
  54. Wang, H., Yuan, H., Li, S., Li, Z. and Jiang, M. (2016), "Synthesis, antimicrobial activity of Schiff base compounds of cinnamaldehyde and amino acids", Bioorg. Med. Chem. Lett., 26, 809-813. https://doi.org/10.1016/j.bmcl.2015.12.089
  55. Yuan, X., Jing, Q., Chen, J. and Li, L. (2017), "Photocatalytic Cr(VI) reduction by mixed metal oxide derived from ZnAl layered double hydroxide", Appl. Clay Sci., 143, 168-174. https://doi.org/10.1016/j.clay.2017.03.034
  56. Zanvettor, N.T., Abbehausen, C., Lustri, W.R., Cuin, A., Masciocchi, N. and Corbi, P.P. (2015), "Silver sulfadoxinate: Synthesis, structural and spectroscopic characterizations, and preliminary antibacterial assays in vitro", J. Mol. Struct., 1082, 180-187. https://doi.org/10.1016/j.molstruc.2014.11.004
  57. Zanvettor, N.T., Nakahata, D.H., Paiva, R.E.F., Ribeiro, M.A., Cuin, A., Corbi, P.P. and Formiga, A.L.B. (2016), "Copper(II), palladium(II) and platinum(II) complexes with 2,2-thiophen-yl-imidazole: Synthesis, spectroscopic characterization, X-ray crystallographic studies and interactions with calf-thymus DNA", Inorg. Chim. Acta., 443, 304-315. https://doi.org/10.1016/j.ica.2016.01.011
  58. Zhang, X., Wei, M., Pu, M., Li, X., Chen, H., Evans, D.G. and Duan, X. (2005), "Preparation and characterization of transRhCl(CO) (TPPTS)2-intercalated layered double hydroxides", J. Solid. State. Chem., 178, 2701-2708. https://doi.org/10.1016/j.jssc.2005.06.008
  59. Zhang, L., Xiong, Z., Li, L., Burt, R. and Zhao, X.S. (2016), "Uptake and degradation of orange II by zinc aluminum layered double oxides", J. Colloid Interf. Sci., 469, 224-230. https://doi.org/10.1016/j.jcis.2016.02.005
  60. Zhang, Q., Jiao, Q., Leroux, F., Tang, P., Li, D. and Feng, Y. (2017), "Antioxidant intercalated Zn-containing layered double hydroxides: preparation, performance and migration properties", New J. Chem., 41, 2364-2371. https://doi.org/10.1039/C6NJ03544B
  61. Zhao, X., Wang, L., Xu, X., Lei, X., Xu, S. and Zhang, F. (2012), "Frabrication and photocatalytic properties of novel ZnO/ZnAl2O4 nanocomposite with ZnAl2O4 dispersed inside ZnO network", AICHE J., 58, 573-582. https://doi.org/10.1002/aic.12597