3-(3,4-Dihydroxyphenyl)-2-Propenoic Acid Synthesis

3-(3,4-Dihydroxyphenyl)-2-Propenoic Acid synthetic thinkingAntimicrobial performance of Co (II) abstruse of 3-(3,4-Dihydroxyphenyl)-2-propenoic acid and sono chemical synthesis of nano dental plate mixed ligand EDA coordination for preparation of CoCl2.6H2O anoparticle nobble3-(3,4-Dihydroxyphenyl)-2-propenoic acid abbreviated as EDA was synthesized and characterized. Co (II) admixture decomposable of this ligand nimble by reaction of chloride flavor with EDA in dry acetonitrile. Phenolic coalesces (a sort of secondary metabolites) argon widely distributed in plants and have assignn to possess germicide properties. Antibacterial activity was canvas for ligand and its metal hard. This complex were tested for their antibacterial drug drug activity against Pseudomonas aeruginosa, Staphylococcus aureus, Streptococcus pyogenes and Escherichia coli comparatively with that of unaffectionate ligand. differential response to phenolic compounds was observed among bacteria. Als o this complex was synthesized in Nano-scale and was characterized by SEM, XDR (X- Ray powder diffraction). Antibacterial activity of complex and nano- material were studied and comp atomic number 18d with each opposite.Keywords 3, 4-dihydroxy benzene acrylic acid, Cu (II) and Co (II) complexes, Antibacterial activity, nano- scaleIntroductionAcrylic acid or hydroxycinnamic acid compounds are widely distributed in the plants. They usually exist number of them exist as free acids in nature 4, 5, 6.Much work has been realized by bioin fundamental as well(p) as medicinal chemists to launch the relationship between the metal ions and their complexes as antimicrobial agents 7-8. Phenolic compounds are secondary plant metabolites and naturally resign in almost all plant materials, including food products of plant origin. These compounds are thought to be an integral part of both human and sensual diets 13. The chemical structure of phenolic acids shows that they are simple phenols. Hy droxycinnamic acid is the major subgroup of phenolic compounds 11,12. Hydroxycinnamates are phenylpropanoid metabolites and occur widely in plants4,and plant products2. Hydroxycinnamates and their derivatives are bioactive plant food ingredients. The other natural ligand from plants such as alkaloids compound also can be used in synthesis of metal complex 1.Nanophasic and nanostructured materials are attracting a great deal of attention because of their capableness for achieving specific processes and selectivity, especially in biological and pharmaceutical applications 3. Nanoparticles are make of natural or artificial polymers ranging 10.In particular, those conjugated with biological moieties have awful potential in drug slant and therapeutic applications. In fact, more progress has been achieved in the past ten years based on inorganic nanomaterials 9.In this context we have undertaken the antimicrobial evaluation of Co (II) complex of 3-(3,4-Dihydroxyphenyl)-2-propenoic ac id. For this purpose the in vitro energy of tow gram compulsory bacteria (Staphylococcus aureus, Streptococcus pyogenes) and tow gram negative bacteria (Pseudomonas aeruginosa, Escherichia coli) to the synthesized compounds was investigated.Materials and MethodsSynthesis of the metal complex General Method3-(3,4-Dihydroxyphenyl)-2-propenoic acid, cobalt chloride was Merck chemicals and was used without barely purification. Organic solvents were reagent grade. electronic spectra were recorded by Camspec UVVisible spectrophotometer representative Perkin Elmer Lambda 25. The IR spectra were recorded using FT-IR Bruker Tensor 27 spectrometer. 1H- NMR was recorded on a Bruker AVANCE DRX 500 spectrometer at 500 and 125MHz respectively. alone the chemical shifts are quoted in ppm using the high-frequency positive convention 1H -NMR spectra were referenced to remote SiMe4. The percent composition of elements was obtained from the Microanalytical Laboratories, Department of Chemistry, University of tarbiyatmoallem, Tehran.A solution of metal salt dissolved in acetonitrile added a dually to a stirred acetonitrile solution of the ligand (EDA), in the molar ratio 11 (metal ligand). The reaction mixture was get ahead stirred for 4-5h to ensure of the completing and precipitation of the formed complexes. Finally, the complexes dried in vacuum desiccators over anhydrous CaCl2.Microorganisms and culture mediaThe following microorganisms were used in this study to test antimicrobial activity of complex. Escherichia coli, Staphylococcus aureus were kindly provided by (anistitue pastor ). The strains were maintained on PD3 agar at 26oC. For long- term storage, glycerin stocks of microorganisms were lively in the corresponding product media with a final glycerine concentration of 12%. The bacterial glycerol stocks were quickly frozen in liquid nitrogen and stored at -80oC.In-vitro anti-bacterial activityAll methodology and travel were followed according to diffusion r ecord book method. An inoculum of 0.5 McFarland standard (1.5*108 cfu/ml) was applied on Mueller Hintonagar (a depth of 4 mm in a petridish of 100 mm diameter) 14. Maximum 6 record books were applied on each plate and they were incubated at 37 C for 24 hours. Z unrivalled of inhibition was circulard including the disc diameter (6mm).Preparation of nanoparticlesCo nanocrystallites were prepared by the reaction of C9H8O4 with Co (C9H7O4) Cl2 in THF as solvent under ultrasound power. Then the suspension was irradiated for 1h with a high- density ultrasonic probe immersed directly into the solution under respective(a) conditions. A maltiwave ultrasonic generator ( sonicator 3000 Italstructure MPD 3000). The samples were characterized with a scanning electron microscope (SEM) with sumptuous coating.Results and DiscussionsStructural description of the complexThe reaction of Co(II) salt with the ligand, EDA, results in the governing body of ML for M=Co (II). complex is quite stable a nd could be stored without any(prenominal) appreciable change. The EDA ligand and the Co(C9H6O4)Cl2.2H2O complex have 223-225C and 195-198C melting orient respectively also complex is insoluble in common organic solvents, such as n-hexane and dichloromethane. However, that is soluble in DMSO, ethanol and DMF. its structure was characterized by elemental analysis, 1H-NMR and IR. Their elemental analyses are in accord with their proposed formula. The spectral entropy of the complexes have good relationship with the literature data.Fig.1. Structure of the ligand, EDA.Analysis of Co ( C9H6O4 ) Cl2.2H2O (EDACC) Dark Blue crystals yield 86% .elemental analyses, 11 metal to ligand stoicheiometry is appoint to all the chelates ( table 1).Table1 Elemental analyses data on the caffeic acid and its Co (II) complex. (31.40) (1.74) (17.15)1H-NMR ( ppm DMSO, 500MHz) 5, 97-7.21 5H, 2q, aroma 11.91 1H, s, acid) 8.98-9,362H, s, alkene. IR absorptions(cm-1 KBr) 1620 (C=C), 972 (=C-H), 1352 (C-O) , 574 (Co-O) and 456 (Co-Cl).The electronic spectral data of the complex in acetonitrile are presented in table 2. there are one peak in spectrum of ligand which can be assigned to * transition. The electronic complex shows a broad band at 680 nm attributable to the 4T1g ( F ) 4 A2g ( F) and the other one at 640- 550 nm attributable to the 4T1g ( F ) 4T1g ( P ) transition for Co( II ) ion .table 2 Electronic spectra of caffeic acid and its Co(II) complex in nmRaman shift (cm1) 500 Co-O), 325 (Co-Cl), 975(C-H), 1618C=C), 1189C-O) (Fig.2.Left).Fig.2. Structure of Co (II) complex with ligand, EDA.In-vitro anti-bacterial activityThe mean diameters of microbial increment inhibited by different complexes are shown in Table 4. All complexes had antimicrobial activity. Inhibition zones larger than 5mm indicated that antimicrobial activity. The data obtained by the disk diffusion method showed that all complexes have antibacterial activity. Among the bacteria, Escherichia coli was the most thin bacteria both ligand and complex Co(C9H7O4)Cl2 Normal- scale had antibacterial effect on this bacteria , whereas only ligand C9H8O4 had antibacterial activity against Streptococcus pyogenes and Pseudomonas aeruginosa . Ligand C9H8O4 and complex Co (C9H7O4) Cl2( Normal- scale) had not any effect against Staphylococcus aureus.Table 4. Zone of growth inhibition of the test compounds against the bacteriaComplex Co (C9H7O4)Cl2 ( Normal scale), had more antibacterial activity against Escherichia coli (14mm) . Complex Co(C9H7O4)Cl2 (Nano scale), had less activity against Staphylococcus aureus (5mm). From these results it may be concluded that there is not any accordance between public scale and nano- scale from the antibacterial activity aspect. The antimicrobial activity of complexes show in this study can be added to the already known effective biological properties of these compounds to the human health.Nanoparticle studyXRD pattern of mixture of caffeic acid andCoCl2 .6H2O p repared by the ultrasonic process is given in Fig. 4. The diffraction peaks accord with the unformed crystal system.Fig.4. The XRD pattern of the mixture of caffeic acid and 6H2O .CoCl2The SEM micrographs of nanostructure are shown in Fig. 5. The nanoparticles show a low degree of crystalline with no defined peaks in the XRD pattern.Fig. 5. SEM images of complex Co (C9H7O4)Cl2The IR spectrum of Co (II) nanostructure (Fig.5) shows the absorption pesk at 574 648 are assigned to the (Co-O) modes, which confirms the formation of Co (II) nanostructure.It has been reported that the negative charge on the prison cubicle surface of Gram-negative bacteria was higher than on positive bacteria (Chunget al., 2004). Due to a higher negative charge on cell surface, theinteraction between Gram-negative bacteria and nanoparticles was definitely stronger than that of Gram-positive bacteria. Moreover, results showed that Gram-positive bacteria were more sensitive to Co (II) nanoparticles.Fig.6. IR Spectrum of complex Co (C9H7O4) Cl2AcknowledgmentsWe thankfully acknowledge the financial support from the Research Council of Ardabil Islamic Azad University and many technological supports that provided by Ardabil University of. edical SciencesReferences1 A.H. Osman, (Synthesis and characterization of cobalt (II) and nickel (II) complexes of fewSchiff bases derived from 3-hydrazino-6-methyl 1, 2, 4 triazin-5(4H) one) Transition Met. Chem, 2006, 31, 35.2 Clifford, 1999 M.N. Clifford, Chlorogenic acids and other cinnamates nature, occurrence and dietary burden, J. Sci. nutrition Agric. 79 (1999), pp. 362372.3 Brigger, I., C. Dubernet, and P. Couvreur. 2002. Nanoparticles in cancer therapy and diagnosis. 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