Abstract
Three new 2-pyrral amino acid Schiff base palladium (II) complexes were synthesized, characterized and their activity against six bacterial species was investigated. The ligands: Potassium 2-pyrrolidine-L-methioninate (L1), Potassium 2-pyrrolidine-L-histidinate (L2) and Potassium 2-pyrrolidine-L-tryptophanate (L3) were synthesized and reacted with dichloro(1,5-cyclooctadiene)palladium(II) to form new palladium (II) complexes C1, C2 and C3, respectively. 1H NMR, FTIR, UV–Vis, elemental analysis and conductivity measurements were used to characterize the products. The antibacterial activities of the compounds were evaluated against Gram-positive Staphylococcus aureus (S. aureus, ATCC 25923), methicillin-resistant Staphylococcus aureus (MRSA, ATCC 33591), Staphylococcus epidermidis (S. epidermidis, ATCC 12228) and Streptococcus pyogenes (S. pyogenes, ATCC 19615) and, gram-negative Pseudomonas aeruginosa (P. aeruginosa, ATCC 27853) and Klebsiella pneumoniae (K. pneumoniae, ATCC 13883) using the agar well diffusion assay and microtitre plate serial dilution method. The palladium complexes were active against the selected bacteria with the imidazole ring containing complex C2 and indole heterocyclic ring containing complex C3 showing the highest activity.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Abdel-Rahman LH, Abu-Dief AM, Ismael M, Mohamed MAA, Hashem NA (2016) Synthesis, structure elucidation, biological screening, molecular modeling and DNA binding of some Cu(II) chelates incorporating imines derived from amino acids. J Mol Struct 1103:232–244. https://doi.org/10.1016/j.molstruc.2015.09.039
Abdel-Rahman LH, Abu-Dief AM, Aboelez MO, Hassan Abdel-Mawgoud AA (2017) DNA interaction, antimicrobial, anticancer activities and molecular docking study of some new VO(II), Cr(III), Mn(II) and Ni(II) mononuclear chelates encompassing quaridentate imine ligand. J Photochem Photobiol B Biol 170:271–285. https://doi.org/10.1016/j.jphotobiol.2017.04.003
Abdel-Rahman LH, Abu-Dief AM, Shehata MR, Atlam FM, Abdel-Mawgoud AAH (2019) Some new Ag(I), VO(II) and Pd(II) chelates incorporating tridentate imine ligand: design, synthesis, structure elucidation, density functional theory calculations for DNA interaction, antimicrobial and anticancer activities and molecular docking studies. Appl Organomet Chem 33:e4699. https://doi.org/10.1002/aoc.4699
Abu-Dief AM, Mohamed IMA (2015) A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-Suef University. J Basic Appl Sci 4:119–133. https://doi.org/10.1016/j.bjbas.2015.05.004
Abu-Surrah AS, Kettunen M (2006) Platinum group antitumor chemistry: design and development of new anticancer drugs complementary to cisplatin. Curr Med Chem 13:1337–1357. https://doi.org/10.2174/092986706776872970
Adinolfi B, Carpi S, Romanini A, Da Pozzo E, Castagna M, Costa B et al (2015) Analysis of the antitumor activity of clotrimazole on A375 human melanoma cells. Anticancer Res 35:3781–3786
AlAjmi MF, Hussain A, Alsalme A, Khan RA (2016) In vivo assessment of newly synthesized achiral copper(ii) and zinc(ii) complexes of a benzimidazole derived scaffold as a potential analgesic, antipyretic and anti-inflammatory. RSC Adv 6:19475–19481. https://doi.org/10.1039/C5RA25071D
Ali MA, Mirza AH, Butcher RJ, Crouse KA (2006) The preparation, characterization and biological activity of Palladium(II) and Platinum(II) complexes of tridentate nns ligands derived from S-methyl- and S-benzyldithiocarbazates and the X-ray crystal structure of the [Pd(mpasme)Cl] complex. Trans Metal Chem 31:79–87. https://doi.org/10.1007/s11243-005-6305-3
Ali OAM, El-Medani SM, Abu Serea MR, Sayed ASS (2015) Unsymmetrical Schiff base (ON) ligand on complexation with some transition metal ions: synthesis, spectral characterization, antibacterial, fluorescence and thermal studies. Spectrochim Acta A Mol Biomol Spectrosc 136:651–660. https://doi.org/10.1016/j.saa.2014.09.079
Alsalme A, Laeeq S, Dwivedi S, Khan MS, Al Farhan K, Musarrat J et al (2016) Synthesis, characterization of α-amino acid Schiff base derived Ru/Pt complexes: induces cytotoxicity in HepG2 cell via protein binding and ROS generation. Spectrochim Acta A Mol Biomol Spectrosc 163:1–7. https://doi.org/10.1016/j.saa.2016.03.012
Arish D, Nair MS (2012) Synthesis, characterization and biological studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with pyrral-l-histidinate. Arab J Chem 5:179–186. https://doi.org/10.1016/j.arabjc.2010.08.011
Asif M, Husain A (2013) Analgesic, anti-inflammatory, and antiplatelet profile of hydrazones containing synthetic molecules. J Appl Chem 2013:7. https://doi.org/10.1155/2013/247203
Balouiri M, Sadiki M, Ibnsouda SK (2016) Methods for in vitro evaluating antimicrobial activity: a review. J Pharmaceut Anal 6:71–79. https://doi.org/10.1016/j.jpha.2015.11.005
Biyala MK, Sharma K, Swami M, Fahmi N, Singh RV (2008) Spectral and biocidal studies of palladium(II) and platinum(II) complexes with monobasic bidentate Schiff bases. Transit Met Chem 33:377–381. https://doi.org/10.1007/s11243-008-9053-3
Chohan ZH, Praveen M, Ghaffar A (1997) Structural and biological behaviour of Co(II), Cu(II) and Ni(II) metal complexes of some amino acid derived Schiff-bases. Met-Based Drugs 4:267–272. https://doi.org/10.1155/mbd.1997.267
Coskun MD, Ari F, Oral AY, Sarimahmut M, Kutlu HM, Yilmaz VT et al (2013) Promising anti-growth effects of palladium(II) saccharinate complex of terpyridine by inducing apoptosis on transformed fibroblasts in vitro. Bioorg Med Chem 21:4698–4705. https://doi.org/10.1016/j.bmc.2013.05.023
Crans DC, Woll KA, Prusinskas K, Johnson MD, Norkus E (2013) Metal speciation in health and medicine represented by iron and vanadium. Inorg Chem 52:12262–12275. https://doi.org/10.1021/ic4007873
Das M, Livingstone SE (1978) Cytotoxic action of some transition metal chelates of Schiff bases derived from S-methyldithiocarbazate. Br J Cancer 37:466–469. https://doi.org/10.1038/bjc.1978.68
Deacon GB, Phillips RJ (1980) Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord Chem Rev 33:227–250. https://doi.org/10.1016/S0010-8545(00)80455-5
Desai NC, Maheta AS, Rajpara KM, Joshi VV, Vaghani HV, Satodiya HM (2014) Green synthesis of novel quinoline based imidazole derivatives and evaluation of their antimicrobial activity. J Saudi Chem Soc 18:963–971. https://doi.org/10.1016/j.jscs.2011.11.021
Devienne KF, Raddi MSG (2002) Screening for antimicrobial activity of natural products using a microplate photometer. Braz J Microbiol 33:166–168
Eicher T, Pozharskii AF, Soldatenkov AT, Katritzky AR (1998) Heterocycles in life and society, 1st edn. Wiley, New York, p 301
Gao E-J, Hong F, Zhu M-C, Ma C, Liang S-K, Zhang J et al (2014) Effect of carbon chain length on biological activity of novel palladium (II) complexes. Eur J Med Chem 82:172–180. https://doi.org/10.1016/j.ejmech.2014.05.021
Garoufis A, Hadjikakou SK, Hadjiliadis N (2009) Palladium coordination compounds as anti-viral, anti-fungal, anti-microbial and anti-tumor agents. Coord Chem Rev 253:1384–1397. https://doi.org/10.1016/j.ccr.2008.09.011
Grünwald KR, Saischek G, Volpe M, Belaj F, Mösch-Zanetti NC (2010) Pyridazine-based ligands and their coordinating ability towards first-row transition metals. Eur J Inorg Chem 2010:2297–2305. https://doi.org/10.1002/ejic.201000120
Guerra W, de Andrade Azevedo E, de Souza Monteiro AR, Bucciarelli-Rodriguez M, Chartone-Souza E, Nascimento AMA et al (2005) Synthesis, characterization, and antibacterial activity of three palladium(II) complexes of tetracyclines. J Inorg Biochem 99:2348–2354. https://doi.org/10.1016/j.jinorgbio.2005.09.001
Heinert D, Martell AE (1962) Pyridoxine and pyridoxal analogs. V. syntheses and infrared spectra of Schiff bases. J Am Chem Soc 84:3257–3263. https://doi.org/10.1021/ja00876a009
Kabak M, Elmali A, Elerman Y (1999) Keto–enol tautomerism, conformations and structure of N-(2-hydroxy-5-methylphenyl), 2-hydroxybenzaldehydeimine. J Mol Struct 477:151–158. https://doi.org/10.1016/S0022-2860(98)00604-8
Kadavakollu S, Stailey C, Kunapareddy CS, White W (2014) Clotrimazole as a cancer drug: a short review. Med Chem 4:722–724. https://doi.org/10.4172/2161-0444.1000219
Kapdi AR, Fairlamb IJS (2014) Anti-cancer palladium complexes: a focus on PdX2L2, palladacycles and related complexes. Chem Soc Rev 43:4751–4777. https://doi.org/10.1039/C4CS00063C
Karamunge KG, Vibhute YB (2013) Synthesis and antimicrobial activity of some new Schiff bases. J Phys Conf Ser 423:012006
Keypour H, Shayesteh M, Rezaeivala M, Chalabian F, Elerman Y, Buyukgungor O (2013) Synthesis, spectral characterization, structural investigation and antimicrobial studies of mononuclear Cu(II), Ni(II), Co(II), Zn(II) and Cd(II) complexes of a new potentially hexadentate N2O4 Schiff base ligand derived from salicylaldehyde. J Mol Struct 1032:62–68. https://doi.org/10.1016/j.molstruc.2012.07.056
Khalid MH, Tokunaga Y, Caputy AJ, Walters E (2005) Inhibition of tumor growth and prolonged survival of rats with intracranial gliomas following administration of clotrimazole. J Neurosurg 103:79–86. https://doi.org/10.3171/jns.2005.103.1.0079
Lever ABP (1984) Inorganic electronic spectroscopy. Elsevier, Amsterdam
Melber CK, Keller D, Mangelsdorf I (2002) Environmental Health Criteria 226: Palladium. World Health Organization
Nagesh GY, Mahendra Raj K, Mruthyunjayaswamy BHM (2015) Synthesis, characterization, thermal study and biological evaluation of Cu(II), Co(II), Ni(II) and Zn(II) complexes of Schiff base ligand containing thiazole moiety. J Mol Struct 1079:423–432. https://doi.org/10.1016/j.molstruc.2014.09.013
Nakamoto K, Morimoto Y, Martell AE (1961) Infrared spectra of metal chelate compounds. IV. Infrared spectra of addition compounds of metallic acetylacetonates1a. J Am Chem Soc 83:4533–4536. https://doi.org/10.1021/ja01483a010
Nyawade EA, Friedrich HB, Omondi B, Chenia HY, Singh M, Gorle S (2015) Synthesis and characterization of new α, α’-diaminoalkane-bridged dicarbonyl(η5-cyclopentadienyl)ruthenium(II) complex salts: antibacterial activity tests of η5-cyclopentadienyl dicarbonyl ruthenium(II) amine complexes. J Organomet Chem 799–800:138–146. https://doi.org/10.1016/j.jorganchem.2015.09.007
Ouf AE-F, Ali MS, Saad EM, Mostafa SI (2010) pH-metric and spectroscopic properties of new 4-hydroxysalicylidene-2-aminopyrimidine Schiff-base transition metal complexes. J Mol Struct 973:69–75. https://doi.org/10.1016/j.molstruc.2010.03.037
Patai S (1970) Analysis of azomethines. Carbon–Nitrogen double bonds. Interscience, New york
Radić GP, Glođović VV, Radojević ID, Stefanović OD, Čomić LR, Ratković ZR et al (2012) Synthesis, characterization and antimicrobial activity of palladium(II) complexes with some alkyl derivates of thiosalicylic acids: crystal structure of the bis(S-benzyl-thiosalicylate)–palladium(II) complex, [Pd(S-bz-thiosal)2]. Polyhedron 31:69–76. https://doi.org/10.1016/j.poly.2011.08.042
Rahman LHA, Abu-Dief AM, Hashem NA, Seleem AA (2015) Recent advances in synthesis, characterization and biological activity of nano sized Schiff base amino acid M(II) complexes. Int J Nanomat Chem 1:79–95
Ramagiri RK, Thupurani MK, Vedula RR (2015) Synthesis, characterization, and antibacterial activity of some novel substituted imidazole derivatives via one-pot three-component. J Heterocycl Chem 52:1713–1717. https://doi.org/10.1002/jhet.2261
Rîmbu C, Danac R, Pui A (2014) Antibacterial activity of Pd(II) complexes with salicylaldehyde-amino acids Schiff bases ligands. Chem Pharmaceut Bull 62:12–15. https://doi.org/10.1248/cpb.c12-01087
Rosenberg B, Vancamp L, Trosko JE, Mansour VH (1969) Platinum compounds: a new class of potent antitumour agents. Nature 222:385–386. https://doi.org/10.1038/222385a0
Samota MK, Seth G (2010) Synthesis, characterization, and antimicrobial activity of palladium(II) and platinum(II) complexes with 2-substituted benzoxazole ligands. Heteroatom Chem 21:44–50. https://doi.org/10.1002/hc.20578
Selvakumar B, Rajendiran V, Uma Maheswari P, Stoeckli-Evans H, Palaniandavar M (2006) Structures, spectra, and DNA-binding properties of mixed ligand copper(II) complexes of iminodiacetic acid: the novel role of diimine co-ligands on DNA conformation and hydrolytic and oxidative double strand DNA cleavage. J Inorg Biochem 100:316–330. https://doi.org/10.1016/j.jinorgbio.2005.11.018
Singh TP, Singh OM (2018) Recent progress in biological activities of indole and indole alkaloids. Mini Rev Med Chem 18:9–25. https://doi.org/10.2174/1389557517666170807123201
Sridhar SK, Pandeya SN, De Clercq E (2001) Synthesis and anti-HIV activity of some isatin derivatives. Boll Chim Farm 140:302–305
Sztanke K, Maziarka A, Osinka A, Sztanke M (2013) An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorg Med Chem 21:3648–3666. https://doi.org/10.1016/j.bmc.2013.04.037
Tabassum S, Asim A, Khan RA, Hussain Z, Srivastav S, Srikrishna S et al (2013) Chiral heterobimetallic complexes targeting human DNA-topoisomerase I[small alpha]. Dalton Trans 42:16749–16761. https://doi.org/10.1039/C3DT51209F
Theuretzbacher U (2011) Resistance drives antibacterial drug development. Curr Opin Pharmacol 11:433–438. https://doi.org/10.1016/j.coph.2011.07.008
Verma A, Joshi S, Singh D (2013) Imidazole: having versatile biological activities. J Chem 2013:10. https://doi.org/10.1155/2013/329412
Wei Q-Y, Xiong J-J, Jiang H, Zhang C, Wen Y (2011) The antimicrobial activities of the cinnamaldehyde adducts with amino acids. Int J Food Microbiol 150:164–170. https://doi.org/10.1016/j.ijfoodmicro.2011.07.034
Wiedermann J, Mereiter K, Kirchner K (2006) Palladium imine and amine complexes derived from 2-thiophenecarboxaldehyde as catalysts for the Suzuki cross-coupling of aryl bromides. J Mol Catal A Chem 257:67–72. https://doi.org/10.1016/j.molcata.2006.04.009
Wilson JJ, Lippard SJ (2014) Synthetic methods for the preparation of platinum anticancer complexes. Chem Rev 114:4470–4495. https://doi.org/10.1021/cr4004314
Yan X, Xu J, Wu X, Zhang Z, Zhang X, Fan Y et al (2015) Proteasome inhibition and cytostatic effects on human cancer cells by pyrazolone-enamines: a combined crystallographic, structural and computational study. New J Chem 39:2168–2180. https://doi.org/10.1039/C4NJ01906G
Yao X, Panichpisal K, Kurtzman N, Nugent K (2007) Cisplatin nephrotoxicity: a review. Am J Med Sci 334:115–124
You Z-L, Shi D-H, Xu C, Zhang Q, Zhu H-L (2008) Schiff base transition metal complexes as novel inhibitors of xanthine oxidase. Eur J Med Chem 43:862–871. https://doi.org/10.1016/j.ejmech.2007.06.015
Zeng L, Gupta P, Chen Y, Wang E, Ji L, Chao H et al (2017) The development of anticancer ruthenium(ii) complexes: from single molecule compounds to nanomaterials. Chem Soc Rev 46:5771–5804. https://doi.org/10.1039/C7CS00195A
Acknowledgements
We would like to thank Jomo Kenyatta University of Agriculture and Technology in Kenya for granting Dr. Eunice Nyawade study leave to undertake this study at the University of the Western Cape, South Africa. We would also like to thank the UWC for allowing us to use their chemistry laboratory to do the synthesis and characterization work, and DST/Mintek Nanotechnology Innovation Centre for perfoming the antibacterial studies.
Funding
This work was supported by the National Research Foundation, South Africa.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Nyawade, E.A., Onani, M.O., Meyer, S. et al. Synthesis, characterization and antibacterial activity studies of new 2-pyrral-L-amino acid Schiff base palladium (II) complexes. Chem. Pap. 74, 3705–3715 (2020). https://doi.org/10.1007/s11696-019-00986-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-019-00986-5