IHJPAS. 36(1)2023 170 This work is licensed under a Creative Commons Attribution 4.0 International License Preparation, Structural Characterization and Biological Activities of Curcumin-Metal(II)-L-3,4-dihydroxyphenylalanin(L-dopa)complexes 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). Keywords: Curcumin, (L-Dopa), α -amino acid and Antimicrobial activity. doi.org/10.30526/36.1.2899 Article history: Received 19 June 2022, Accepted 28 Augest 2022, Published in January 2023. Ibn Al-Haitham Journal for Pure and Applied Sciences Journal homepage: jih.uobaghdad.edu.iq Hala Mohammed Salh Department of Chemstry , College of Education for Pure Sciences, Ibn Al – Haitham, University of Baghdad, Baghdad, Iraq. hala.mohammed1205a@ihcoedu.uobaghdad.edu.iq Taghreed H Al-Noor Department of Chemstry , College of Education for Pure Sciences, Ibn Al – Haitham, University of Baghdad, Baghdad, Iraq. drtaghreed2@gmail.com https://creativecommons.org/licenses/by/4.0/ mailto:hala.mohammed1205a@ihcoedu.uobaghdad.edu.iq mailto:drtaghreed2@gmail.com IHJPAS. 36(1)2023 171 1.Introduction α -amino - acid, L-3,4-dihydroxyphenylalanin(L- dopa) derivatives used as building blocks to generate protein [1,2] It also in humans, behaves like a hormone in the circulatory system with Alzheimer's and Parkinson's diseases. A tetradentate (N2O2) Schiff base (H2Ldfm) was successfully synthesized via condensation of curcumin / diferuloylmethane (dfm) and L-leucine amino acid (HL) [3]. The bacteriostatic effects `of L-dopa complexes shown to be more pitent than L-dopa .Brien et al. (2021), have been reported synthesis, cis-Bis(L-dopa -2N, O) Cu (II).H2O [5]. Rama et al, chemical speciation of ternary complexes of L-dopa and1,10-phenanthroline as [(metal: (L-dopa): (phena)] [(metal: (L-dopa): 2 (phena)] molar ratios . metal: Co(II), Ni(II) and Cu(II) in 30% v/v, 2-propanediol–water mixtures [6]. Curcumin, is a yellow coloring and have many functional groups as a polyphenolic natural pigment, a powerful natural chelating agent by conjugated β-diketone moiety and shown to exhibit biological properties: anti-viral, anticancer, anti-inflammatory, anti-bacterial,anti-fungal, and anti- oxidant activities and the requirement to treat Alzheimer's diseases [6]. Curcumin ingreses the sencentivy cells to cisplatin through down-regulation of FEN1 [7]. Complexation of curcumin with metals ions Al(III), Ga(III), Se(II) and metal oxides of rare earth ions were synthesized, 1 : 1 and 1 : 2(metal/ion),respectively[8]. The Curcumin complexes of the Schiff Base [ (Curc )- L-Tyrosine] with Pb(II) , Al(III), and Ag(I) Ions constitute an especially interesting series of compounds. [9]. Complexation of curcumin with transition metals were synthesized, characterized and evaluated for various biological activities [10]. L-dopa Curcumin Figure1. The Structures of L-dopa and Curcumin In this work, we synthetic and characterized of some complexes derives from Curcumin, as a primary ligand and (L- dopa)as a secondary ligand Figure1. 2.Experimental 2-1. Materials and physical measurements: All solvents and reagents were obtained from Sigma-Aldrich and used without further purification. Metal salts [Zn(II), Cu(II), Ni(II), Co(II) Cd(II), and Mn(II) ] as chlorides.The melting points using Stuart SRS –USA of the complexes . Ultraviolet-visible spectra were obtained using solvent(10−3M-DMSO) between (200 to 1100) nm for comparison by U.V 160A - Shimadzu).The Fourier-transform infrared spectra were recorded using KBr pellets at range (400‐ 4000 cm−1).on FTIR 8400-S. Shimadzu spectrophotometry.The Conductivity measurements of the compounds ( 10−3mol/L in DMSO) were obtained using digital Ino-Labro.720- conductivity.M% recorded by using atomic absorption spectrophotometer Shimadzu -A. A 620. https://en.wikipedia.org/wiki/Natural_pigment https://en.wikipedia.org/wiki/Natural_pigment IHJPAS. 36(1)2023 172 2-2. General Procedure for the Synthesis of Complexes 1–8 [11]. Preparation of potassium-2-aminohydroxytyrosine,Levodopa, 3-(3,4-dihydroxyphenyl)-L (L- dopa- K+): The amino acid L- 2-amino-3-(3,4-dihydroxyphenyl) propanoic-acid [0.394 g,2 m mol]was dissolved in 20 mL H2O/ethanol(50%) mixture containing KOH (0.112 g, 2 mmol) in a flask and stirred at (30 ºC), the solution of ligand (L-dopa) was deprotonated to L-dopalanilate ion by using (KOH)according to the Scheme 1 Scheme 1. The Elucidation (L-dopa- K+) Preparation of Complexes: [11]. Molar ratio M: Cur: (L-dopa),[1 :1 : 2]. A mixture of (1 mmol)curcumine,and(2 mmol) (L-dopa- K+)in 50mL ethanol/water [1:1] v/v was added to the metal chloride (1 mmol) in the least amount of distilled water. The reaction mixture was prepared for 30 min with constant stirring to ensure complete formation of the complexes. The precipitated solid complexes were filtered, washed for several times with 50% (v/v) ethanol/water and recrystallized in ethanol, and dried in vacuum over anhydrous CaCl2. 3.Results and Discussion Generally, the complexes were prepared by reacting the respective metal salts with the ligands using [Cur:M: (L-dopa)2] mole ratio, i.e. one mole of curcumin , one mole of metal salt and two mole of (L- dopa) [9] as the following equations: 2(L-dopa) +2KOH→ 2 (L-dopa- K+) + 2H2O 2 (L-dopa- K+) + Curc +MCl2.nH2O → [M(Curc) (L-dopa)2] + nH2O + 2KCl n= 0 …6 {where (Curc) is Curcumin and [L-3,4-dihydroxyphenylalanin(L-dopa)]: as shown Scheme 2. IHJPAS. 36(1)2023 173 Scheme 2. Route the synthesis of [M(Curc)(L-dopa)2] complexes Scheme 3. Zwitterion of (L-dopa) IHJPAS. 36(1)2023 174 Table 1. Physico-chemical data of the [M (Curc)( L-Dopa)2]complexes The method of preparation of complexes to be reproducible, yielding 92-98% of products. recrystallization purified all complexes from ethanol and have yellow to orange. The physical and analytical data of complexes were listed in Table 1. The melting point range was between 182- 256◦C. The melting points of the (L-dopa) ligand were higher than that of the metal complexes but Compounds yield Colour m.p °C Λm 1000 L/C ohm -1 - cm 2 - mol -1 in DMSO1 0 -3 M Found (Calc.)% C H N M 1 -L Mn(Curc)([ ] 2dopa) Dark brown 187-185 0.60 57.43 )57.00( 3.43 (3.8 8) 6.74 (6.77) 6.74 (7.2) 2 ]2dopa)-L Fe(Curc)([ bright brown 185-183 0.88 57.36 )57.00( 3.43 (4.0 0) 6.84 (6.70) 6.84 (7.7) 3 ]2dopa)-LCo(Curc)([ yellow 184-182 0.56 57.15 )56.17( 3.42 (3.0 0) 7.19 (6.88) 7.19 (8.2) 4 ]2dopa)-)(LNi(Curc[ Dark yellow 186-184 0.36 57.16 )58.61( 3.42 (3.0 0) 7.16 (6.08) 7.16 (8.2) 5 ]2dopa)-LCu(Curc)([ bright brown 188-185.5 0.55 56.83 )57.01( 3.40 (3.0 0) 7.71 (6.88) 7.71 (8.7) 6 ] 2dopa)-LZn(Curc)([ yellow 190-188.7 0.84 56.70 )55.50( 3.39 (3.0 0) 7.92 (6.88) 7.92 (8.2) 7 ]2dopa)-LCd(Curc)([ yellow 220-222 1.80 53.65 (57.01) 3.21 (3.0 0) 12.87 (12.00) 12.87 (13.3) 8 [Hg(Curc)(L-dopa)2] yellowish brown 256 1.05 48.73 (47.31) 2.91 (3.0 0) 20.87 (20.00) 20.87 (…….) IHJPAS. 36(1)2023 175 lower for (Curc). The results of elemental analyses (C.H.N) for complexes were found to be in agreement with the proposed molecular formulae of the complexes. Most of the compounds are soluble in water and most common organic solvents like DMF, DMSO and acetone.ΛM (1×10−3 M,DMSO): (Molar conductance 0.36- 0.84 (ohm-1.cm2.mol-1 - non-electrolyte nature). [10]. The test for chloride ion with AgNO3 solution was negative (Nil%) indicating that there is no (Cl-) outside the coordination sphere of the central metal. Table 1, propose that the complexes are formed in 1:1:2 [M:Curc: (L-dopa)2 )] ratio. [12-13]. IR spectra of [M (Curc)( L- dopa)2] complexes (1-8) IR spectrum of zwitterion of (L- dopa) as shown in scheme 3 is shows strong broad absorption 3432( br,-OH), 3112 (C-H stretching) , (3200 cm-1) might be due to νOH - stretching and at 3066cm-1 due to the νas(+NH3) and at stretching νs(+NH3)( 2927 cm -1.The stretching of the – NH2group of free L- doba were observed at 3387 cm -1 , and bending vibrations at 817 cm-1 ,The ν (CH3) and ν (CH) groups appeard around (3000 - 2835) cm –1 overlap with the ν amino group. 1557 νC=C Phenyl ring stretching's, [14]. 1095 aromatic δνC-H bending, The (L-dopa) spectrum show two absorption at 1570 cm–1and 1448 cm–1 belong to νasym (-COO−) and νsym(-COO−) respectively Figure 2.[15-16]. The energy difference Δ ν =200 cm–1,in complexes , indicates coordination between (-COO–) group of (L-dopa) and metal ions via oxygen atom. The spectrum of (Curc) Table 2. The were observed broad band in recovery (3059-3475) cm-1 corresponding to a (phenolic hydrogen -bonded compound) and at 1627 cm-1 due to ν (C=O). bands due to (C- O- C) at 1157Cm-1. 3066 (Ar- C - H) and 1438 (Ar- C= C) [11]. and has two at (1626 and 1601 )Cm- 1 depicated to the whith CO group conjugated with C =C double bonds [16-17] The (L-dopa) coordinated to M (II) as a mono negative bidentate ligand through the oxygen atom(O) of the (-COO−)and the (N), atom of the amine(-NH2) group Table 2. The appearance of these bands supported the coordination of the (L-dopa) ligand to the metal ions through oxygen and nitrogen atoms. while (Curc) coordinates as a neutral bidentate through (O) in the (C=O) group. New bands at 428-497 cm-1 and 520-601 cm-1 were observed and assigned to v(M-O) and v (M-N), respectively, which are absent in both free ligands [16-20]. Figure 2. FT-IR spectrum of (L-dopa) IHJPAS. 36(1)2023 176 The geometry of all complexes were posted from the position of the bands in the electronic spectra and observed values of magnetic moments (μeff) which are summarized in Table 3. The (UV-Vis) spectrum of the (Curc) in DMSO Figure 3 exhibits two absorption peaks, (λmax 440 nm)( 22727 cm-1) and (λmax 270 nm,37037 cm-1) can be due either to an n- π* transition or to a combination of π- π*,and n→π*transitions respectively, in the ketone ( C=O ) group agree with data reported [19]. The (UV-Vis) spectrum for the (L-dopa) Figure 4 exhibits two absorption peaks, (λmax 451 nm, 22727 cm-1) and (λmax 277 nm.37037 cm-1) due to an n→π*transition [22,23]. In Zn ((II)), Hg ((II)),andCd ((II)) complexes, are (Dimegnetic) with octahedral environment., , d10 orbitals are completely filled exhibit charge transfer(C.T), [17-18]. IHJPAS. 36(1)2023 177 Table 2. Characteristic IR (KBr) Vmax frequencies in (cm-1)of complexes Compound Phenol (Ar- OH) v(NH2) ν(C-H) Aromatic ν(C-H) Aliphatic ν(C=O) Keton ν(C=O) COO asy, sym ν (C=C) Δ ν COO - ( (asym-sym) ν (M-N) ν (M-O) -Mn(Curc)(L[ ] 2dopa) 3506 3375 3012 2843 1508 1627 1427 1458 200 520 428 ]2dopa)-Fe(Curc)(L[ 3502 3414 3012 2943 1508 1627 1427 1462 200 574 428 ]2dopa)-Co(Curc)(L[ 3506 3417 3012 2974 1508 1627 1427 1458 200 574 428 ]2dopa)-Ni(Curc)(L[ 3506 3300 3136 3016 2943 1508 1627 1427 1458 200 597 424 ]2dopa)-Cu(Curc)(L[ 3506 - 3012 2943 1508 1627 1427 1458 200 597 497 ]2dopa)-Zn(Curc)(L[ 3506 3275 3012 2843 1508 1627 1427 1458 200 543 466 ]2dopa)-Cd(Curc)(L[ 3510 3406 3128 3016 2978 1508 1627 1427 1458 200 601 451 ]2dopa)-Hg(Curc)(L[ 3510 3414 3290 3039 2920 1589 1627 1427 1450 216 597 451 IHJPAS. 36(1)2023 178 Figure 3. Electronic - Spectrum of the (Curc ) Figure 4. Electronic - Spectrum of the (L-dopa) IHJPAS. 36(1)2023 179 Table 3. Electronic spectral data of the (Curc - M- L-dopa) metal complexes 4. Biological activities The in-vitro biological activity of the the synthesized compunds in DMSO and all the plates were incubated at 370C and were tested against the bacterial [Escherichia coli,and Staphylococcus aureus] and Candida albicans by well diffusion method using nutrient agar as medium. The results were tabulated in Table 4,showed DMSO used as solvent negative control as it did not show any activity against bacteria,.Two ligands showed antimicrobial activity against gram-positive and gram negative bacteria and against Candida albicans. [26] All complexes possess biological activity[20 ] and which have the same activities. All tested of [M (Curc)(L-dopa)2] mixed-ligand complexes were detected the same activities and good antimicrobial activity, displayed higher activities candida albicans fungus compared to bacteria.as show in Table 4 Figure 5 and Chart 1 [24-26],.Antifungal studies towards all tested fungi enhanced activity when coordinated with all metals, on chelation the polarity of the ion due to the overlap of the ligand orbital and partial sharing of the positive charge of the ion with donor groups reduced to a greater extent [27,28] . Complexes λ nm Cm - ν ϵ Max Assignments μB ] 2dopa )-Mn(Curc)( L[ 273 435 765 36630 22988 13071 376 1584 33 n→π* Charge transfer 6A1g (S) →4T1g 5.4 ]2dopa )-Fe(Curc)( L[ 270 436 795 843 37037 22935 12578 11862 580 2014 27 26 π →π* n →π* A1g →4T1g A1g→4T2g 4.11 ]2dopa )-Co(Curc) ( L[ 270 436 752 800 934 37037 22935 13297 12500 10706 362 1369 13 13 11 π→ π* 4T1g(F) → 4T2g(F), T1g(F) → 4T1g(P) T1g(F) → 4A2g(F) 4.62 ]2dopa )-Ni(Curc)( L[ 270 437 809 37037 22883 123609.93 314 1260 15 n→π* Charge transfer (p)g1T 3→ (F)g2A 3 3.01 ]2dopa )-Cu(Curc)( L[ 271 436 934 36900 22935 10706 350 1465 3 n→π* CT 2Eg → 2T2g 2.04 ] 2dopa )-Zn(Curc)( L[ 270 435 37037 22988 301 1251 * Charge transfer 0.0 ]2dopa)-Cd(Curc)( L[ 267 436 37453 22935 11350 596 2138 33 * Charge transfer 0.0 [Hg (Curc)(L-dopa)2] 267 435 37453 22988 659 2239 * Charge transfer 0.0 http://www.ijpsonline.com/article.asp?issn=0250-474X;year=2010;volume=72;issue=2;spage=216;epage=222;aulast=Neelakantan#ref16 IHJPAS. 36(1)2023 180 Table 4. Zone of inhibition, (ZI) diameter in mm of the[M (Curc)(L-dopa)2] complexes Comp. staphylococus aureus klebsiella pneumonie candida albicans )6O20H21Curc (C 12 17 25 )2NO7H3dopa) (C-( L 16 18 20 DMSO 0 0 0 1 ]2dopa)-Mn(Curc)(L[ 12 20 19 2 ]2dopa)-Fe(Curc)(L[ 13 20 13 3 ]2dopa)-Co(Curc)(L[ 14 20 20 4 ]2dopa)-Ni(Curc)(L[ 13 20 11 5 ]2dopa)-Cu(Curc)(L[ 14 20 27 6 ]2dopa)-Zn(Curc)(L[ 16 20 20 7 ]2dopa)-Cd(Curc)(L[ 16 15 30 8 ]2dopa)-Hg (Curc)(L[ 15 15 30 IHJPAS. 36(1)2023 181 Figure 5. The Inhibition zone (ZI) of compounds IHJPAS. 36(1)2023 182 Chart 1. The (ZI) mm of ligands and [M (Curc)(L-dopa)2] complexes (1-8) 5. Proposed molecular structure Examining complexes based on the above analysis, the data indicated the existence of (Hexa- coordinate - an octahedral geometry around M(II). The proposed structures of [M(II)-(Curc)-(L-dopa) ] are shown in Figure 6. Figure 6. Probable 3-D structure of the complexes IHJPAS. 36(1)2023 183 6.Conclusion The synthetic direction adopted for the synthesis of new complexes was very simple with good yield. Eight new mixed ligand metal(II) coordination compounds have been prepared by using curcumin,L-dopa and appropriate metal chloride, in 1:1:2 Curc:M:2 L-dopa molar ratio , M= Mn (II), Fe (II),Co(II) ,Ni(II),Cu (II), Zn(II), Cd(II) and Hg(II). The results suggest that octahedral symmetry for the all complexes which the curcumin and L-dopa may act as bidentate ligands. L- dopa probably binds to the metal ions in the mono-deprotonated. The antibacterial activity studies were done using agar well diffusion technique and the result shows that the complexes have higher antibacterial activity than the free ligand. The ligands and their corresponding metal complexes were evaluated for biologically active, the complexes show better activity than the free ligands. 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