Preparation, Structural Characterization and Biological Activities of Curcumin-Metal(II)-L-3,4-dihydroxyphenylalanin (L-dopa) complexes
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Abstract
In the present work, a first-row divalent d-transition metal obtained from curcumin(Curc) and L-3,4-dihydroxyphenylalanin(L-dopa)have been synthesized which their complexes and characterized by C.H.N, conductance, spectral methods: FT-IR, Ultra–Visible. Magneto-chemical measurements, molar conductance ΛM (1×10−3 mol/L in DMSO):36- 0.84 ohm-1.cm2.mol-1 (non-electrolyte).
The data shows that the complexes have the structure [M((II))-(Curc)-(L-dopa)] system. Electronic and magnetic data suggest an octahedral geometry for all complexes in which the (L-dopa) and curcumin act as bidentate ligands.
Curcumin coordinated to the metal ions M (II) through the lone pair of electrons of oxygen in 2(C=O) groups. The (L-dopa) coordinated to M (II) as a mono negative bidentate ligand through the oxygen atom of the carboxylate and the (N), atom of the (-NH2) groups.
The general formula was given for the prepared mixed ligand complexes as [M (Cur)(L-dopa)2 ]. M= Mn (II), Fe (II),Co(II),Ni(II),Cu (II), Zn(II), Cd(II) and Hg(II).The ligands and their metal complexes were screened for their antimicrobial activity klebsiella pneumonie,and Staphylococcus aureus, and Candida albicans. Metal chelates showed very good antimicrobial activity than their parent curcumin-and (L- dopa).
We have given the general formula for the prepared mixed ligand complexes as [M (Cur)(L-dopa)2].M= Mn (II), Fe (II),Co(II) ,Ni(II),Cu (II), Zn(II), Cd(II) and Hg(II).The ligands and their metal complexes were screened for their antimicrobial activity klebsiella pneumonie,and Staphylococcus aureus, and Candida albicans. Metal chelates show very good antimicrobial activity than their parent Curcumin-and (L- dopa).
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Kiss, T.; Gergely. A. Copper (II) and nickel (II) ternary complexes of L-dopa and related compounds. Journal of inorganic biochemistry, 1985, 25, 247-259, https://doi.org/10.1016/0162-0134(85)80024-6
Ostrov, D. A.; Alkanani,A.; McDaniel, K. A.; Case, S.; Baschal, E. E.; Pyle, L.; Michels, A. W. Methyldopa blocks MHC class II binding to disease-specific antigens in autoimmune diabetes. The Journal of clinical investigation, 2018, 128, 1888-1902, https://doi.org/10.1172/JCI97739
Ali, A. M.; Al-Noor, T. H. Synthesis, spectroscopic study, biological activity and dyeing application of curcumin-Schiff base with various metal ions complexes. IOP Conf. Ser.: Mater. Sci. Eng, 2021, 1046, 012006, 10.1088/1757-899X/1046/1/012006
Tosato, M.; Di Marco, V. Metal chelation therapy and Parkinson’s disease: A critical review on the thermodynamics of complex formation between relevant metal ions and promising or established drugs. Biomolecules, 2019, 9, 269 https://doi.org/10.3390/biom9070269
O'Brien, P.; Poyner, E. A.; Alraddadi,T. S.; Hursthouse, M. B.; Foxman, B. M. cis-Bis (l-DOPA-κ2N, O) copper (II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry. Acta Crystallographica Section C: Structural Chemistry, 2021, 77, 383-390, https://doi.org/10.1107/S2053229621006082.
Raju Bendi, R.; Santhee Devi Karri, V.; Rao Gollapalli, N. Chemical speciation of ternary complexes of L-dopa and 1,10-phenanthroline with Co(II), Ni(II) and Cu(II) in low dielectric media. Chemical Speciation and Bioavailability, 2012, 24, 10.3184/095422912X13324388533472
Hussain, Y.; Islam, L.; Khan, H.; Filosa, R.; Aschner, M.; Javed, S. Curcumin-cisplatin chemotherapy: A novel strategy in promoting chemotherapy efficacy and reducing side effects. Phytother. Res, 2021, 35, 6514–6529. https://doi.org/10.1002/ptr.7225
Barik, A.; Mishra, B.; Kunwar, A.; Kadam, R. M.; Shen, L.; Dutta,S.; Priyadarsini,K. I. Comparative study of copper(II)ecurcumin complexes as superoxide dismutase mimics and free radical scavengers. European journal of medicinal chemistry, 2007, 42, 431-439, https://doi.org/10.1016/j.ejmech.2006.11.012
Ali, A. M.; Al-Noor, T. H.; Abdalrazaq, E.; Jbarah, A. A. Q. Synthesis and DFT Study of the Complexation of Schiff Base Derived Curcumin and L-Tyrosine with Al (III), Ag (I), and Pb (II) Metal Ions. Indonesian Journal of Chemistry, 2021, 21, 708-724, https://doi.org/10.22146/ijc.62188
Baira, K.; Ounissi, A.; Merouani, H.; Alam, M.; Ouddai, N.; Erto, A.; Yadav, K. K.; Islam, S.; Cheon, J.-K.; Jeon, B.-H. Multitask Quantum Study of the Curcumin-Based Complex Physicochemical and Biological Properties. J. Mol.Sci, 2022, 23, https://doi.org/10.3390/ijms23052832
Alkhafagi, Z. H.; Al-Noor,T. H. Synthesis, characterization and antimicrobial studies of mixed ligand from phthalic acid and 1, 10-phenanthroline with their complexes. AIP Conference Proceedings, 2020, 2290, https://doi.org/10.1063/5.0028226
Geary, W. J. The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 1971, 7, 81-122, https://doi.org/10.1016/S0010-8545(00)80009-0
Abu-Dief, A. M.; Nassr, L. A. Tailoring, physicochemical characterization, antibacterial and DNA binding mode studies of Cu (II) Schiff bases amino acid bioactive agents incorporating 5-bromo-2-hydroxybenzaldehyde. Journal of the Iranian Chemical Society, 2015, 12, 943-955, DOI 10.1007/s13738-014-0557-9
Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry; John Wiley and Sons, Inc: 1999, http://repository.vnu.edu.vn/handle/VNU_123/85212
Nakamoto, K. Infrared and Raman spectra of inorganic and coordination compounds, part B: applications in coordination, organometallic, and bioinorganic chemistry; John Wiley & Sons, 2009.
Vlad, M.; Labadi, L.; Sasca, V.; Saity, L.; Costisor, O. Synthesis and thermal decomposition of the coordination polymer of 4, 4’-bipyridine and oxalate anion with Cu (II) and VO (IV). Chem. Bull. Chem. Bull. Politechnica Univ. Timisoara, 2006, 51, 17-19.
Calatayud, M. L.; Castro, I.; Sletten, J.; Lloret, F.; Julve, M. Syntheses, crystal structures and magnetic properties of chromato-, sulfato-, and oxalato-bridged dinuclear copper (II) complexes. Inorganica Chimica Acta, 2000, 300, 846-854, https://doi.org/10.1016/S0020-1693(99)00590-3
Barthes, M.; Vik, A. F.; Spire, A.; Bordallo, H. N.; Eckert, J. Breathers or structural instability in solid L-alanine: a new IR and inelastic neutron scattering vibrational spectroscopic study. The Journal of Physical Chemistry A, 2002, 106, 5230-5241, https://doi.org/10.1021/jp015615c
Bodkhe. A. S.; Patil. S. S.; Shaikh. M. M. Synthesis, characterization and antibacterial studies on mixed ligand copper complexes with polydentate ligands. Acta Poloniae Pharmaceutica, 2012, 69, 871-877, ISSN 0001-6837.
Deka, B.; Bhattacharyya, A.; Mukherjee, S.; Sarkar, T.; Soni, K.; Banerjee, S.; Hussain, A. Ferrocene conjugated copper (II) complexes of terpyridine and traditional Chinese medicine (TCM) anticancer ligands showing selective toxicity towards cancer cells. Applied Organometallic Chemistry, 2018, 32, e4287 https://doi.org/10.1002/aoc.4287
Lever, A. B. P., Inorganic Electronic Spectroscopy; Netherlands, 1984, ISSN 0167-6881.
Singh, P.D; Jha, N.K.; Mishra, L. K. Complexes of 2, 4-dimercapto-s-triazolo-[4, 3-b]-1, 3, 4-thiadiazole with some bivalent metal ions—I. Journal of Inorganic and Nuclear Chemistry, 1980, 42, 282-285, https://doi.org/10.1016/0022-1902(80)80258-2.
Shriver, D. W., ; Atkins, P. W., Inorganic chemistry, electronic spectra of TM complexes: Freeman; New York; 2006.
Patel, K. S.; Patel, J. C.; Dholariya, H. R.; Patel, V. K.; Patel, K. D. Synthesis of Cu (II), Ni (II), Co (II), and Mn (II) complexes with ciprofloxacin and their evaluation of antimicrobial, antioxidant and anti-tubercular activity. Open Journal of Metal, 2012, 2, DOI:10.4236/ojmetal.2012.23008
Reiss, A.; Florea, S.; Caproiu,T.; Stanica, N. Synthesis, characterization, and antibacterial activity of some transition metals with the Schiff base N-(2-furanylmethylene)-3-aminodibenzofuran. Turkish Journal of Chemistry, 2009, 33, 775-783 doi:10.3906/kim-0807-31
Mohapatra, R. K.; El-ajaily, M. M.; Alassbaly,F. S.; Sarangi, A. K.; Das, D.; Maihub,A. A.; Al-Noor. T. H. DFT, anticancer, antioxidant and molecular docking investigations of some ternary Ni (II) complexes with 2-[(E)-[4-(dimethylamino) phenyl] methyleneamino] phenol. Chemical Papers, 2021, 75, 1005-1019, https://doi.org/10.1007/s11696-020-01342-8
Singh, K.; Kumar, Y.; Puri, P.; Sharma, C.; Aneja, K. R. Antimicrobial, spectral and thermal studies of divalent cobalt, nickel, copper and zinc complexes with triazole Schiff bases. Arabian Journal of Chemistry, 2017, 10, S978-S987, https://doi.org/10.1016/j.arabjc.2012.12.038
abdul karem, Lekaa K.; Al-Noor,T.H. Synthesis, Spectral and Bacterial Studies of Mixed Ligand Complexes of Schiff Base Derived from Methyldopa and Anthranilic Acid with Some Metal Ions. Ibn Al-Haitham Journal for Pure and Applied scienc, 2017, 235-247, https://doi.org/ 10.30526/2017.IHSCICONF.1797.