Metal (II) Complexes of some Carboxylic group Drugs: Chelation, Characterization, Antibacterial, Analgesic, and Toxicology Studies Biological Potentials of Carboxylic Group Drug Complexes
Iranian Journal of Pharmaceutical Sciences,
Vol. 17 Núm. 4 (2021),
1 October 2021
,
Página 47-64
https://doi.org/10.22037/ijps.v17.40238
Resumen
The present work focuses on the synthesis and biological evaluation of metal complexes of mixed acetylsalicylic acid and para-aminobenzoic acid in ratio 1:1:1 to give a complex type: [M(ASA)(PABA)(H2O)n(Cl2)x](Cl2)y (where M = Cu(II), Cd(II), Ni(II), Fe(III), or Mn(II); ASA = Acetylsalicylic acid; PABA = para-aminobenzoic acid; n = 0 or 2; x = 0 or 1; y = 0 or 1). The metal complexes were obtained by a refluxing method and characterized by elemental analysis, melting point, conductivity measurements, ultraviolet-visible absorption, and infrared spectroscopy. The conductance measurement indicates the non-electrolytic nature of the complexes. The octahedral environment has been proposed for the complexes except for Cd (II) complex. The level of toxicity of the synthesized complexes was determined in vivo. [Cu(ASA)(PABA)(H2O)2], [Cd(ASA)(PABA)]Cl2, and [Mn(ASA)(PABA)(H2O)2] exhibited higher enzymatic activities in the serum and kidney homogenates of the Wister rats investigated. The acetic acid-induced writhing model method was used in the evaluation of the analgesic activities of the prepared complexes. Metal complexes of Cu (II), Cd(II), Ni(II), Fe(III), and Mn(II) exhibited percentage writhing inhibition of 67.61, 43.87, 60.42, 70.45, and 52.34 % respectively. The complexes proved to be more effective than their parent-free ligands with Fe (III) possessing the highest analgesic potentials. The in vitro antimicrobial activity against bacterial strains was studied using the agar well diffusion procedure. It was also observed that the complexes exhibited higher bacteriostatic activities than the free ligands.
- Acetylsalicylic acid
- Antibacterial
- Enzymatic activities
- Metal complexes
- para-aminobenzoic acid Toxicity
- Serum chemistry
Cómo citar
Citas
[2] Cuzick J, Thorat MA, Bosetti C, Brown PH, Burn J, Cook NR, Ford LG, Jacobs EJ, Jankowski JA, La Vecchia C, Law M, Meyskens F, Rothwell PM, Senn HJ and Umar A. Estimates of benefits and harms of prophylactic use of aspirin in the general population. Ann. Oncol. (2015) 26 (1): 47-57.
[3] Solomon EI, Heppner DE, Johnston EM, Ginsbach J, Cirera J, Qayyum M, Kieber-Emmons MT, Kjaergaard CH, Hadt RG and Tian L. Copper active sites in biology. Chem. Rev. (2014) 114 (7): 3659-853.
[4] Dikio CW, Ejidike IP, Mtunzi FM, Klink MJ and Dikio ED. Hydrazide Schiff bases of acetylacetonate metal complexes: Synthesis, spectroscopic and biological studies. Int. J. Pharm. Pharm. Sci. (2017) 9 (12):257-67.
[5] Abdul Wahid AAR, Abdulkareem HR and Kadhim ZN. Synthesis, characterization and analytical studies of Schiff base, their transition metal complexes and their polymers. Irq. Nat. J. Chem. (2018) 18 (4): 166-83.
[6] Sun RWY, Ma DL, Wong ELM and Che CM. Some uses of transition metal complexes as anti-cancer and anti-HIV agents. Dalton Trans. (2007) 43: 4884-92.
[7] Ejidike IP and Ajibade PA. Synthesis, spectroscopic, antibacterial and free radical scavenging studies of Cu(II), Ni(II), Zn(II) and Co(II) complexes of 4,4'-{ethane-1,2-diylbis[nitrilo(1E)eth-1-yl-1-ylidene]}dibenzene-1,3-diol Schiff base. J. Pharm. Sci. Res. (2017) 9(5): 593-600.
[8] Khanna S, Singh P, Kau H and Joon A. Synthesis, characterization and antimicrobial investigation of mixed ligand complexes of Cobalt(II) and Nickel(II) with P-dimethylaminobenzaldehyde thiosemicarbazone. MJChem. (2019) 21 (3):100-9.
[9] Agwara MO, Ndosiri NB, Mohamadou A and Condé AM. Synthesis, characterization and antimicrobial evaluation of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of pyridine-2-carboxylic acid. RJPBCS. (2013) 4 (2):1370-81. [10] Ejidike, I.P., Cu (II) complexes of 4-[(1E)-N-{2-[(Z)-Benzylidene-amino]ethyl}ethanimidoyl]benzene-1,3-diol Schiff base: Synthesis, spectroscopic, in-vitro antioxidant, antifungal and antibacterial studies. Molecules (2018) 23:1581.
[11] Bamigboye MO, Quadri LA, Ejidike IP and Ahmed RN. Biochemical and haematological changes in Wister rats after administration of nickel- and copper-drug complexes of isonicotinic acid hydrazide. Int. J. Med. Rev. (2020) 7 (2): 64-70.
[12] Scalese G, Machado I, Fontana C, Salinas G, Pérez-Díaz L and Gambino D. Heteroleptic Oxidovanadium (V) complexes with activity against infective and non-infective stages of Trypanosoma cruzi. Molecules (2021) 26 (17): 5375.
[13] Ogodo UP and Abosede OO. Synthesis and characterization of Cu (II) complexes of salicylate ligands. J. Appl. Sci. Environ. Manage. (2018) 22 (12): 1961-64.
[14] Krátký M, Konečná K, Janoušek J, Brablíková M, Janďourek O, Trejtnar F, Stolaříková J and Vinšová J. 4-Aminobenzoic acid derivatives: converting folate precursor to antimicrobial and cytotoxic agents. Biomolecules (2020) 10 (1): 9.
[15] Obasi LM, Oruma US, Al-Swaidan IA, Ramasami P, Ezeorah CJ and Ochonogor AE. Synthesis, characterization and antibacterial studies of N-(benzothiazol-2-yl)-4-chlorobenzenesulphonamide and its neodymium(III) and thallium(III) complexes. Molecules (2017) 22 (2): 153.
[16] Hoda P, Bahare H, Saghavaz NF and Mehran D. Synthesis, characterization and antibacterial activity of novel 1,3-diethyl-1,3-bis(4-nitrophenyl)urea and its metal(II) complexes. Molecules (2017) 22(12): 2125.
[17] Kundu SP, Sultan Z, Rahman A, Paul SK, Shikder S, Kundu S, Amran S and Hossain A. The study of analgesic activity of complexes of magnesium sulfate with aspirin, paracetamol and naproxen. Clin. Pharmacol. Biopharm. (2015) 4 (3): 143.
[18] Yemitan OK and Adeyemi OO. Mechanistic assessment of the analgesic, anti-inflammatory and antipyretic actions of Dalbergia saxatilis in animal models. Pharmaceutical Biology (2017) 55(1): 898-905.
[19] Ogunniran KO., Ajanaku KO, James OO, Ajani OO, Adekoya JA and Nwinyi OC. Synthesis, characterization, antimicrobial activity and toxicology study of some metal complexes of mixed antibiotics. Afri. J. Pure Appli. Chemistry (2008) 2 (7): 69-74.
[20] Naglah AM, Al-Omar MA, El-Megharbel SM and Refat MS. Structural, conductometric and antimicrobial investigations of ibuprofen analgesic drug complexes with certain metal ions. Int. J. Pharmacol. (2015) 11 (7): 773-85.
[21] Olanrewaju AA, Ibeji CU and Festus SF. Synthesis, characterization, and computational studies of metal (II) complexes derived from β-diketone and para-aminobenzoic acid. Indian J. Heterocycl. Chem. (2018) 28 (3): 351-61.
[22] Demirezen N, Tarınç D, Polat D, Ceşme M, Gölcü A and Tümer M. Synthesis of trimethoprim metal complexes: Spectral, electrochemical, thermal, DNA-binding and surface morphology studies. Spectrochim. ActaA Mol. Biomol. Spectrosc. (2012) 94: 243-55.
[23] Lobana TS, Indoria S, Jassal AK, Kaur H, Arora DS and Jasinski JP. Synthesis, structures, spectroscopy and antimicrobial properties of complexes of copper (II) with salicylaldehyde n-substituted thiosemicarbazones and 2,2‘-bipyridine or 1,10-phenanthroline. Eur. J. Med. Chem. (2014) 76: 145-54.
[24] Bamigboye MO and Ejidike IP. Synthesis, characterization, antimalarial and antimicrobial activities of mixed Ibuprofen-Pyrimethamine M(II) complexes [M = Cd, Co, Zn, Mn]. Natural & Applied Sciences Journal (2019) 2(2): 38-50.
[25] Raman A, Sakthivel N and Pravin N. Exploring DNA binding and nucleolytic activity of few 4-aminoantipyrine based amino acid Schiff base complexes: A comparative approach. Spectrochim Acta A Mol. Biomol. Spectrosc. (2014) 125: 404-13.
[26] Abu-El-Wahab ZH and El-Sarrag MR. Derivative of phosphate Schiff base transition metal complexes: Synthesis, studies and biological activity. Spectrochim Acta A Mol. Biomol. Spectrosc. (2004) 60:271-7.
[27] Mohammed GG and Abdel-Wahab ZH. Mixed ligand complexes of bis(phenylimine) Schiff base ligands incorporating pyridinium moiety: Synthesis, characterization and antibacterial activity. Spectrochim Acta A Mol. Biomol. Spectrosc. (2005) 9 (61): 2231-8.
[28] Tella AC and Obaleye JA. Synthesis and biological studies of Co (II) and Cd (II) 5-(3, 4, 5-trimethoxybenzyl) pyrimidine-2, 4-diamine (Trimethoprim) complexes. Int. J. Biol. Chem. Sci. (2010) 4(6): 2181-91.
[29] Arise RO, Olowo A, Acho MA, Olufemi O,Adewale AA and Tella AC. Efficacy and safety
properties of Lumefantrine-Trimethoprim-Copper
complex in mice. Ceylon J. Sci. (2018) 47: 347.
- Resumen ##plugins.themes.ojsPlusA.frontend.article.viewed##: 97 ##plugins.themes.ojsPlusA.frontend.article.times##
- IJPS_Volume 17_Issue 4_Pages 47-64 (English) ##plugins.themes.ojsPlusA.frontend.article.downloaded##: 64 ##plugins.themes.ojsPlusA.frontend.article.times##