{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T11:09:40Z","timestamp":1787656180495,"version":"build-2736575974"},"reference-count":33,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2020,9,16]],"date-time":"2020-09-16T00:00:00Z","timestamp":1600214400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Deanship of Scientific Research at Princess Nourah Bint Abdulrahman University though the Fast-Track Research Funding Program Saudi Arabia.","award":["Fast track Program"],"award-info":[{"award-number":["Fast track Program"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The microbial resistance to current antibiotics is increasing day by day, which in turn accelerating the development of new effective drugs. Several studies have proved the high antimicrobial potential of the interaction of several organic ligands with a variety of metal ions. In the present study, a conventional method has been adopted in the synthesis of twelve new heteroleptic complexes of cobalt (II), nickel (II), copper (II) and zinc (II) using three aldimines, namely, (HL1 ((E)-2-((4-chloro-2-hydroxybenzylidene)amino)-3,4-dimethyl-5-phenylcyclopent-2-en-1-one), HL2 ((Z)-3-((4-chlorobenzylidene)amino)-4-hydroxy-5-nitrobenzenesulfonic acid) HL3 (2,2\u2032-((1,2-phenylenebis(azaneylylidene))bis(methaneylylidene))diphenol)) as primary ligands, while phenyl glycine was the secondary ligand. The synthesized compounds were characterized by UV-vis, IR and multinuclear (1H and 13C) NMR spectroscopy, elemental analysis, and electrical conductance. The IR study revealed the coordination of the aldimine derivatives with the -OH and N atom of imine moiety. In contrary to this, the phenyl glycine coordinated to the metal ions via oxygen of carboxylate and nitrogen of the amino group. The spectroscopic analysis unveiled the tetrahedral geometry of the synthesized metal (II) complexes, except for ligand HL3 which exhibited octahedral geometry. The synthesized compounds generally showed antibacterial activity for all microbes, except Ni (II) complexes lacking sensitivity. Furthermore, to access the bioavailability, the synthesized complexes were screened for their solubilization in the micellar media of sodium lauryl sulphate. The metal complex\u2013surfactant interaction was revealed by UV-vis spectroscopy and electrical conductivity measurements.<\/jats:p>","DOI":"10.3390\/molecules25184252","type":"journal-article","created":{"date-parts":[[2020,9,16]],"date-time":"2020-09-16T10:30:12Z","timestamp":1600252212000},"page":"4252","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["New Heteroleptic 3D Metal Complexes: Synthesis, Antimicrobial and Solubilization Parameters"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5343-6893","authenticated-orcid":false,"given":"Muhammad Babar","family":"Taj","sequence":"first","affiliation":[{"name":"Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan"},{"name":"Department of Chemistry, University of Sahiwal, Sahiwal 57000, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5647-1237","authenticated-orcid":false,"given":"Muneera D. F.","family":"Alkahtani","sequence":"additional","affiliation":[{"name":"Department of Biology, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh 11675, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Uzma","family":"Ali","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Quaid-e-Azam University, Islamabad 44000, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ahmad","family":"Raheel","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Quaid-e-Azam University, Islamabad 44000, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Walla","family":"Alelwani","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Science, University of Jeddah, Jeddah 80203, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5670-1688","authenticated-orcid":false,"given":"Afnan M.","family":"Alnajeebi","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Science, University of Jeddah, Jeddah 80203, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nouf Abubakr","family":"Babteen","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Faculty of Science, University of Jeddah, Jeddah 80203, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4709-0029","authenticated-orcid":false,"given":"Sadia","family":"Noor","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Agriculture, Faisalabad 38040, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2858-408X","authenticated-orcid":false,"given":"Heba","family":"Alshater","sequence":"additional","affiliation":[{"name":"Department of Forensic Medicine and Clinical Toxicology, Menoufia University, Shbien El-Kom 32511, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,9,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"539","DOI":"10.2217\/fmb.16.2","article-title":"The potential role of trimethoprim-sulfamethoxazole in the treatment of drug-resistant tuberculosis","volume":"11","author":"Palomino","year":"2016","journal-title":"Future Microbiol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"12409","DOI":"10.1039\/C6DT00625F","article-title":"Unique mononuclear Mn II complexes of an end-off compartmental Schiff base ligand: Experimental and theoretical studies on their bio-relevant catalytic promiscuity","volume":"45","author":"Adhikary","year":"2016","journal-title":"Dalton Trans."},{"key":"ref_3","first-page":"119","article-title":"A review on versatile applications of transition metal complexes incorporating Schiff bases","volume":"4","author":"Mohamed","year":"2015","journal-title":"Beni-Suef Univ. J. Basic Appl. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1205","DOI":"10.1135\/cccc20001205","article-title":"Bioremediation of heavy metal pollution exploiting constituents, metabolites and metabolic pathways of livings. A review","volume":"65","author":"Kotrba","year":"2000","journal-title":"Collect. Czech. Chem. Commun."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/j.molstruc.2007.02.023","article-title":"Unsymmetrical Schiff bases functionalize as bibasic tetradentate (ONNO) and monobasic tridentate (NNO) ligands on complexation with some transition metal ions","volume":"872","author":"Rabie","year":"2008","journal-title":"J. Mol. Struct."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2753","DOI":"10.2174\/092986705774462950","article-title":"Essentiality, toxicology and chelation therapy of zinc and copper","volume":"12","author":"Cai","year":"2005","journal-title":"Curr. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3228","DOI":"10.3390\/molecules15053228","article-title":"Vitamin B12: Unique metalorganic compounds and the most complex vitamins","volume":"15","author":"Randaccio","year":"2010","journal-title":"Molecules"},{"key":"ref_8","first-page":"200","article-title":"The importance of mineral elements for humans, domestic animals and plants-A review","volume":"4","author":"Soetan","year":"2010","journal-title":"Afr. J. Food Sci."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4921","DOI":"10.1021\/ja0429115","article-title":"Zn protein simulations including charge transfer and local polarization effects","volume":"127","author":"Sakharov","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","first-page":"244","article-title":"Relationship between the architecture of zinc coordination and zinc binding affinity in proteins\u2013insights into zinc regulation","volume":"7","author":"Drozd","year":"2015","journal-title":"METAJS"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3052","DOI":"10.1021\/acs.accounts.8b00415","article-title":"Mixed-Ligand Metal\u2013Organic Frameworks and Heteroleptic Coordination Cages as Multifunctional Scaffolds\u2014A Comparison","volume":"51","author":"Pullen","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1039\/B916237B","article-title":"Transition-metal phosphors with cyclometalating ligands: Fundamentals and applications","volume":"39","author":"Chi","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_13","first-page":"5058","article-title":"In vitro antibacterial and antifungal activity of Iraqi propolis","volume":"5","author":"Hendi","year":"2011","journal-title":"J. Med. Plants Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1016\/j.jphotobiol.2016.06.052","article-title":"Sonochemical synthesis, DNA binding, antimicrobial evaluation and in vitro anticancer activity of three new nano-sized Cu (II), Co (II) and Ni (II) chelates based on tri-dentate NOO imine ligands as precursors for metal oxides","volume":"162","year":"2016","journal-title":"J. Photochem. Photobiol. B."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2100","DOI":"10.1021\/cr300222d","article-title":"Cation\u2212 \u03c0 interaction: Its role and relevance in chemistry, biology, and material science","volume":"113","author":"Mahadevi","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_16","first-page":"1786","article-title":"Schiff Bases and their Metal Complexes as Potential Anticancer Candidates: A Review of Recent Works","volume":"19","author":"Tadele","year":"2019","journal-title":"Anti-Cancer Agents Med. Chem. (Former. Curr. Med. Chem.-Anti-Cancer Agents)"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"110868","DOI":"10.1016\/j.jinorgbio.2019.110868","article-title":"Synthesis, DNA binding studies, and antiproliferative activity of novel Pt (II)-complexes with an L-alanyl-based ligand","volume":"203","author":"Riccardi","year":"2020","journal-title":"J. Inorg. Biochem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.msec.2017.11.004","article-title":"Synthesis, spectroscopic, thermal and molecular modeling studies of Zn2+, Cd2+ and UO22+ complexes of Schiff bases containing triazole moiety. Antimicrobial, anticancer, antioxidant and DNA binding studies","volume":"83","author":"Gaber","year":"2018","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.21123\/bsj.2010.7.2.1006-1013","article-title":"Preparation, Characterization and Antimicrobial Activity Study of Some Transition Metal Complexes of 4-Flourophenyl-4-Nitrobenzylidene","volume":"7","author":"Ahmed","year":"2010","journal-title":"Baghdad Sci. J."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1007\/s10973-007-8712-5","article-title":"Synthesis and characterization of bis (nicotinamide) m-hydroxybenzoate complexes of Co (II), Ni (II), Cu (II) and Zn (II)","volume":"93","year":"2008","journal-title":"J. Therm. Anal. Calorim."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Gautam, S., Bundela, P., Pandey, A., Awasthi, M., and Sarsaiya, S. (2012). Diversity of cellulolytic microbes and the biodegradation of municipal solid waste by a potential strain. Int. J. Microbiol., 2012.","DOI":"10.1155\/2012\/325907"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"862","DOI":"10.3389\/fchem.2019.00862","article-title":"Heteroleptic metal complexes of a pyrimidinyl based Schiff base ligand incorporating 2, 2\u2032-bipyridine moiety: Synthesis, characterization and biological studies","volume":"7","author":"Festus","year":"2019","journal-title":"Front. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7186","DOI":"10.3390\/ijms12107186","article-title":"Metal complexes of diisopropylthiourea: Synthesis, characterization and antibacterial studies","volume":"12","author":"Ajibade","year":"2011","journal-title":"Int. J. Mol. Sci."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1007\/s11164-011-0371-2","article-title":"Cytotoxicity, antioxidant, and antimicrobial activities of novel 2-quinolone derivatives derived from coumarin","volume":"38","author":"Saour","year":"2012","journal-title":"Res. Chem. Intermed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"6833","DOI":"10.3390\/molecules16086833","article-title":"The use of umbelliferone in the synthesis of new heterocyclic compounds","volume":"16","author":"Musa","year":"2011","journal-title":"Molecules"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Osowole, A.A., Ott, I., and Ogunlana, O.M. (2012). Synthesis, spectroscopic, anticancer, and antimicrobial properties of some metal (II) complexes of (substituted) nitrophenol Schiff base. Int. J. Inorg. Chem., 2012.","DOI":"10.1155\/2012\/206417"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1016\/j.molliq.2017.05.052","article-title":"Spectroscopic and conductometric study of interaction of anionic surfactants with [Co(phen)3]F2\u00b72H2O complex","volume":"240","author":"Younas","year":"2017","journal-title":"J. Mol. Liq."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"100240","DOI":"10.1016\/j.colcom.2020.100240","article-title":"Thermodynamic, spectroscopic and biological investigation of interaction of anionic surfactants with [Cu(im)6]F2\u00b74H2O complex in aqueous solution","volume":"35","author":"Younas","year":"2020","journal-title":"Colloid Interface Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.colcom.2018.09.004","article-title":"Spectroscopic, conductometric and biological investigation of [Ni(phen)3]F2.EtOH.MeOH.8H2O complex in anionic micellar media","volume":"27","author":"Noor","year":"2018","journal-title":"Colloid Interface Sci."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.1007\/s11743-017-1997-x","article-title":"Solubilization of Ni imidazole complex in micellar media of anionic surfactants, sodium dodecyl sulfate and sodium stearate","volume":"20","author":"Younas","year":"2017","journal-title":"J. Surfactants Deterg."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/j.jinorgbio.2017.08.006","article-title":"Molar absorption coefficients and stability constants of Zincon metal complexes for determination of metal ions and bioinorganic applications","volume":"176","author":"Pomorski","year":"2017","journal-title":"J. Inorg. Biochem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"985","DOI":"10.1021\/j150541a040","article-title":"Conductances of concentrated aqueous sodium and potassium chloride solutions at 25","volume":"60","author":"Chambers","year":"1956","journal-title":"J. Phys. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1411","DOI":"10.1021\/ja01343a020","article-title":"The electrolytic conductivity of some uni-univalent electrolytes in water at 25","volume":"54","author":"Shedlovsky","year":"1932","journal-title":"J. Am. Chem. Soc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/18\/4252\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:10:35Z","timestamp":1760177435000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/18\/4252"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,9,16]]},"references-count":33,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2020,9]]}},"alternative-id":["molecules25184252"],"URL":"https:\/\/doi.org\/10.3390\/molecules25184252","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,9,16]]}}}