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Synthesis, antimicrobial activity, theoretical investigation, and electrochemical studies of cellulosic metal complexes

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Abstract

In this explanation, we explained how to make 5-amino-1,3,4-thiadiazol cellulose by reacting carboxymethyl cellulose (CMC) with thiosemicarbazide and undergoing intermolecular cyclization in the presence of acid medium (2R,3R,4S,5R,6R). This was confirmed by spectral analysis to be -6-(((5-amino-1,3,4-thiadiazol-2-yl)methyl)-2,5-dimethoxytetrahydro-2H-pyran-3,4-diol (CMSC) (4). Moreover, the 1,3,4-thiazole cellulose 4 reacts with the ligand metal chlorides at a ratio of 1:2 to produce the corresponding new metal complexes. Additionally, the obtained complexes were examined using FT-IR, SEM, TGA, and UV spectroscopy, which demonstrated that the chelation of the amino group of the thiadiazole with the OH of the CMC and the presence of Cd(II), Cu(II), and Fe(III) completely altered the morphology of the CMC fibers, resulting in tiny needles on the surface and coating most of the CMC. Additionally, these complexes were shown to have antimicrobial properties, with the Cu(II) complex cellulose demonstrating excellent antimicrobial activity in comparison with other complexes. It was also demonstrated through docking with various proteins, including (PDB ID:3t88), (PDB ID:2wje), (PDB ID:4ynt), (PDB ID:1tgh), that the Cu(II) complex was more stable than other complexes. Using cyclic voltammetry, the surface oxidation and reduction of these complexes as well as their capacity for reactivity were verified. Also, these complexes' physical descriptors were explained to determine their reactivity using the DFT/B3PW91/LANDZ2 basis set.

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References

  1. E.M. Akl, S. Dacrory, M.S. Abdel-Aziz, S. Kamel, A.M. Fahim, Preparation and characterization of novel antibacterial blended films based on modified carboxymethyl cellulose/phenolic compounds. Polym. Bull. 78, 1061–1085 (2021)

    Article  CAS  Google Scholar 

  2. M. Duque-Acevedo, L.J. Belmonte-Ureña, F.J. Cortés-García, F. Camacho-Ferre, Agricultural waste: review of the evolution, approaches and perspectives on alternative uses. Glob. Ecol. Conserv. 22, e00902 (2020)

    Article  Google Scholar 

  3. A.M. Fahim, E.E. Abu-El Magd, Performance efficiency of MIP OH polymers as organic filler on cellulose pulp waste to form cellulosic paper sheets with biological evaluation and computational studies. Polym. Bull. 79, 4099–4131 (2021)

    Article  Google Scholar 

  4. A.M. Fahim, E.E. Abu-El Magd, Enhancement of Molecular imprinted polymer as organic fillers on bagasse cellulose fibers with biological evaluation and computational calculations. J. Mol. Struct. 1241, 130660 (2021)

    Article  CAS  Google Scholar 

  5. S. Dacrory, S. Kamel, Magnetic composite based on cellulose and GO for latent fingerprint visualization. Egypt. J. Chem. 65, 1–6 (2022)

    Google Scholar 

  6. H. Bayrak, A.M. Fahim, F.Y. Karahalil, I. Azafad, G.M. Boyraci, E. Taflan, Synthesis, antioxidant activity, docking simulation, and computational investigation of novel heterocyclic compounds and Schiff bases from picric acid. J. Mol. Struct. 1281, 135184 (2023). https://doi.org/10.1016/j.molstruc.2023.135184

    Article  CAS  Google Scholar 

  7. M. Abdelraof, M.S. Hasanin, M.M. Farag, H.Y. Ahmed, Green synthesis of bacterial cellulose/bioactive glass nanocomposites: effect of glass nanoparticles on cellulose yield, biocompatibility and antimicrobial activity. Int. J. Biol. Macromol. 138, 975–985 (2019)

    Article  CAS  PubMed  Google Scholar 

  8. A.M. Fahim, R.E. Abouzeid, S.A. Al Kiey, S. Dacrory, Development of semiconductive foams based on cellulose-benzenesulfonate/CuFe2O4-nanoparticles and theoretical studies with DFT/B3PW91/LANDZ2 basis set. J. Mol. Struct. 1247, 131390 (2022)

    Article  CAS  Google Scholar 

  9. A.H. Hashem, M. Hasanin, S. Kamel, S. Dacrory, A new approach for antimicrobial and antiviral activities of biocompatible nanocomposite based on cellulose, amino acid and graphene oxide. Colloids Surf. B Biointerfaces 209, 112172 (2022)

    Article  CAS  PubMed  Google Scholar 

  10. S. Dacrory, A.H. Hashem, S. Kamel, Antimicrobial and antiviral activities with molecular docking study of chitosan/carrageenan@ clove oil beads. Biotechnol. J. 17, 2100298 (2022)

    Article  CAS  Google Scholar 

  11. M. Hasanin, A. El-Henawy, W.H. Eisa, H. El-Saied, M. Sameeh, Nano-amino acid cellulose derivatives: eco-synthesis, characterization, and antimicrobial properties. Int. J. Biol. Macromol. 132, 963–969 (2019)

    Article  CAS  PubMed  Google Scholar 

  12. A. Salama, M. Hasanin, P. Hesemann, Synthesis and antimicrobial properties of new chitosan derivatives containing guanidinium groups. Carbohydr. Polym. 241, 116363 (2020)

    Article  CAS  PubMed  Google Scholar 

  13. A. Aboelnaga, E. Mansour, A.M. Fahim, G.H. Elsayed, Synthesis, anti-proliferative activity, gene expression, docking and DFT investigation of novel Pyrazol-1-yl-thiazol-4 (5H)-one derivatives. J. Mol. Struct. 1251, 131945 (2021)

    Article  Google Scholar 

  14. A. Asmaa, M.F. Asmaa, H.E.L.S. Taghreed, Computer aid screening for potential antimalarial choroquinone compounds as Covid 19 utilizing computational calculations and molecular docking study. OnLine J. Biol. Sci. 20, 207–220 (2020)

    Article  Google Scholar 

  15. H.S. Magar, E.E. Abu-El Magd, R.Y.A. Hassan, A.M. Fahim, Rapid impedimetric detection of cadmium ions using Nanocellulose/ligand/nanocomposite (CNT/Co3O4). Microchem. J. 182, 107885 (2022). https://doi.org/10.1016/j.microc.2022.107885

    Article  CAS  Google Scholar 

  16. M. Al-Ibrahim, H.-K. Roth, M. Schroedner, A. Konkin, U. Zhokhavets, G. Gobsch, P. Scharff, S. Sensfuss, The influence of the optoelectronic properties of poly(3-alkylthiophenes) on the device parameters in flexible polymer solar cells. Org. Electron. 6, 65–77 (2005)

    Article  CAS  Google Scholar 

  17. A.M. Fahim, H.S. Magar, N.H. Mahmoud, Synthesis, anti-proliferative activities, docking studies, and computational calculations of novel isonicotinic mixed complexes. Appl. Organomet. Chem. 36(5), e6616 (2022). https://doi.org/10.1002/aoc.6616

    Article  CAS  Google Scholar 

  18. A. Mohamed, A.M. Fahim, M.A. Ibrahim, Theoretical investigation on hydrogen bond interaction between adrenaline and hydrogen sulfide. J. Mol. Model. 26, 1–13 (2020)

    Article  Google Scholar 

  19. I.H.I. Habib, H.N.A. Hassan, R. Attar. New alternative cyclic voltammetry for HOMO and LUMO estimation of organic materials. Under preparation for the publication. 2021

  20. A. Attia, A. Aboelnaga, A.M. Fahim, Isonicotinohydrazide chalcone base and its Ni complex as corrosion inhibitors during acid cleaning: theoretical and experimental approaches. Egypt. J. Chem. (2022). https://doi.org/10.21608/ejchem.2022.166142.7046

    Article  Google Scholar 

  21. A.M. Fahim, Anti-proliferative activity, molecular docking study of novel synthesized ethoxyphenylbenzene sulfonamide with computational calculations. J. Mol. Struct. 1277, 134871 (2023)

    Article  CAS  Google Scholar 

  22. A.M. Fahim, H.S. Magar, N.H. Mahmoud, Synthesis, antimicrobial, antitumor activity, docking simulation, theoretical studies, and electrochemical analysis of novel Cd(II), Co(II), Cu(II), and Fe(III) complexes containing barbituric moiety. Appl. Organomet. Chem. 2023, e7023 (2023)

    Google Scholar 

  23. F. Josefík, T. Mikysek, M. Svobodová, P. Šimůnek, H. Kvapilová, J. Ludvik, New triazaborine chromophores: their synthesis via oxazaborines and electrochemical and DFT study of their fundamental properties. Organometallics 33, 4931–4939 (2014)

    Article  Google Scholar 

  24. D.P. Rillema, S.R. Stayanov, A.J. Cruz, H. Nguyen, C. Moore, W. Huang, K. Siam, A. Jehan, V. KomReddy, HOMO-LUMO energy gap control in platinum(II) biphenyl complexes containing 2,2′-bipyridine ligands. Dalton Trans. 44, 17075–17090 (2015)

    Article  CAS  PubMed  Google Scholar 

  25. T. Mikysek, H. Kvapilova, F. Josefík, J. Ludvik, Electrochemical and theoretical study of a new series of bicyclic oxazaborines. Anal. Lett. 49, 178–187 (2016)

    Article  CAS  Google Scholar 

  26. Inc. CCG, Molecular Operating Environment (MOE) (Chemical Computing Group Inc, Montreal, 2016)

    Google Scholar 

  27. H.-J. Li, X. Li, N. Liu, H. Zhang, J.J. Truglio, S. Mishra, C. Kisker, M. Garcia-Diaz, P.J. Tonge, Mechanism of the intramolecular Claisen condensation reaction catalyzed by MenB, a crotonase superfamily member. Biochemistry 50, 9532–9544 (2011)

    Article  CAS  PubMed  Google Scholar 

  28. G. Hagelueken, H. Huang, I.L. Mainprize, C. Whitfield, J.H. Naismith, Crystal structures of Wzb of Escherichia coli and CpsB of Streptococcus pneumoniae, representatives of two families of tyrosine phosphatases that regulate capsule assembly. J. Mol. Biol. 392, 678–688 (2009)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. H. Yoshida, G. Sakai, K. Mori, K. Kojima, S. Kamitori, K. Sode, Structural analysis of fungus-derived FAD glucose dehydrogenase. Sci. Rep. 5, 1–13 (2015)

    Article  Google Scholar 

  30. Z. Juo, T. Chiu, P. Leiberman, I. Baikalov, A.J. Berk, R.E. Dickerson, J. Mol. Biol. 261, 239–254 (1996)

    Article  CAS  PubMed  Google Scholar 

  31. B.W. D’Andrade, S. Datta, S.R. Forrest, P. Djurovich, E. Polikarpov, M.E. Thompson, Relationship between the ionization and oxidation potentials of molecular organic semiconductor. Org. Electron. 6, 11–20 (2005)

    Article  Google Scholar 

  32. P.I. Djurovich, E.I. Mayo, S.R. Forrest, M.E. Thompson, Measurement of the lowest unoccupied molecular orbital energies of molecular organic semiconductors. Org. Electron. 10, 515–520 (2009)

    Article  CAS  Google Scholar 

  33. Z.-L. Gua, J.B. Kim, H. Wang, C. Jaye, D.A. Fischer, Y.-L. Loo, A. Kahn, Direct determination of the electronic structure of the poly(3-hexylthiophene):phenyl-[66]-C61 butyric acid methyl ester blend. Org. Electron. 11, 1779–1785 (2010)

    Article  Google Scholar 

  34. H.B. Schlegel, Optimization of equilibrium geometries and transition structures. J. Comput. Chem. 3, 214–218 (1982)

    Article  CAS  Google Scholar 

  35. Gaussian JJIWC. 09, revision A. 02 (Gaussian, 2009)

  36. A.M. Fahim, A.M. Farag, A. Mermer, H. Bayrak, Y. Şirin, Synthesis of novel β-lactams: antioxidant activity, acetylcholinesterase inhibition and computational studies. J. Mol. Struct. 1233, 130092 (2021)

    Article  CAS  Google Scholar 

  37. A. Fahim, E. Ismael, Synthesis, antimicrobial activity and quantum calculations of novel sulphonamide derivatives. Egypt. J. Chem. 62, 1427–1440 (2019)

    Google Scholar 

  38. A.P. Imeson, Thickening and Gelling Agents for Food (Springer, 2012)

    Google Scholar 

  39. E.M. Zayed, M.A. Zayed, A.M. Fahim, F.A. El-Samahy, Synthesis of novel macrocyclic Schiff’s-base and its complexes having N2O2 group of donor atoms. Characterization and anticancer screening are studied. Appl. Organomet. Chem. 31, e3694 (2017)

    Article  Google Scholar 

  40. N.H. Mahmoud, A.A.A. Emara, W. Linert, A.M. Fahim, A.A. Abou-Hussein, Synthesis, spectral investigation, biological activities and docking stimulation of novel metal complexes of Trifluoro phenylthiazol derivative with computational studies. J. Mol. Struct. 1272, 134095 (2023)

    Article  CAS  Google Scholar 

  41. A.M. Fahim, H.S. Magar, M.A. Ayoub, Synthesis, characterization, thermal studies, electrochemical behavior, antimicrobial, docking studies, and computational simulation of triazole-thiol metal complexes. Appl. Organomet. Chem. 36(5), e6647 (2022). https://doi.org/10.1002/aoc.6647

    Article  CAS  Google Scholar 

  42. S. Dacrory, H. Abou-Yousef, S. Kamel, G. Turky, Development of biodegradable semiconducting foam based on micro-fibrillated cellulose/Cu-NPs. Int. J. Biol. Macromol. 132, 351–359 (2019)

    Article  CAS  PubMed  Google Scholar 

  43. A.M. Fahim, H.A. Ghabbour, M.M. Kabil, S.T. Al-Rashood, H.A. Abdel-Aziz, Synthesis, X-ray crystal structure, Hirshfeld analysis and computational investigation of bis(methylthio)acrylonitrile with antimicrobial and docking evaluation. J. Mol. Struct. 1260, 132793 (2022)

    Article  CAS  Google Scholar 

  44. P.X. Gao, Y. Ding, W. Mai, W.L. Hughes, C. Lao, Z.L.J.S. Wang, Conversion of zinc oxide nanobelts into superlattice-structured nanohelices. Science 309, 1700–1704 (2005)

    Article  CAS  PubMed  Google Scholar 

  45. A. Youssef, M. Hasanin, M. Abd El-Aziz, G.M. Turky, Conducting chitosan/hydroxylethyl cellulose/polyaniline bionanocomposites hydrogel based on graphene oxide doped with Ag-NPs. Int. J. Biol. Macromol. 167, 1435–1444 (2021)

    Article  CAS  PubMed  Google Scholar 

  46. M.A. Shalaby, A.M. Fahim, S.A. Rizk, Microwave-assisted synthesis, antioxidant activity, docking simulation, and DFT analysis of different heterocyclic compounds. Sci. Rep. 13, 4999 (2023). https://doi.org/10.1038/s41598-023-31995-w

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. H. Abou-Yousef, S. Dacrory, M. Hasanin, E. Saber, S. Kamel, Biocompatible hydrogel based on aldehyde-functionalized cellulose and chitosan for potential control drug release. Sustain. Chem. Pharm. 21, 100419 (2021)

    Article  CAS  Google Scholar 

  48. S. Dacrory, A.H. Hashem, M. Hasanin, Synthesis of cellulose based amino acid functionalized nano-biocomplex: characterization, antifungal activity, molecular docking and hemocompatibility. Environ. Nanotechnol. Monit. Manag. 15, 100453 (2021)

    CAS  Google Scholar 

  49. H. Elsayed, M. Hasanin, M. Rehan, Enhancement of multifunctional properties of leather surface decorated with silver nanoparticles (Ag NPs). J. Mol. Struct. 1234, 130130 (2021)

    Article  CAS  Google Scholar 

  50. S. Vilar, G. Cozza, S. Moro, Medicinal chemistry and the molecular operating environment (MOE): application of QSAR and molecular docking to drug discovery. CTMC 8, 1555–1572 (2008)

    Article  CAS  Google Scholar 

  51. Y.U. Cebeci, H. Bayrak, ŞA. Karaoğlu, A.M. Fahim, Synthesis of novel antipyrine-azole-S-alkyl derivatives antimicrobial activity, molecular docking, and computational studies. J. Mol. Struct. 1260, 132810 (2022)

    Article  CAS  Google Scholar 

  52. J.C. Costa, R.J. Taveira, C.F. Lima, A. Mendes, L.M. Santos, Optical band gaps of organic semiconductor materials. Opt. Mater. 58, 51–60 (2016)

    Article  CAS  Google Scholar 

  53. A. Frisch. Gaussian 09W Reference (Wallingford, 2009).

  54. H.A. Ghabbour, A.M. Fahim, M.A. Abu El-Enin, S.T. Al-Rashood, H.A. Abdel-Aziz, Crystal structure, Hirshfeld surface analysis and computational study of three 2-(4-arylthiazol-2-yl)isoindoline-1,3-dione derivatives. Mol. Cryst. Liq. Cryst. (2022). https://doi.org/10.1080/15421406.2022.2045794

    Article  Google Scholar 

  55. A.M. Fahim, M.S. Elshikh, N.M. Darwish, Synthesis, antitumor activity, molecular docking and DFT study of novel pyrimidiopyrazole derivatives. Curr. Comput. Aided Drug Des. 16, 486–499 (2020)

    Article  CAS  PubMed  Google Scholar 

  56. A.M. Fahim, B. Wasiniak, J.P.C. Łukaszewicz, Molecularly imprinted polymer and computational study of (E)-4-(2-cyano-3-(dimethylamino) acryloyl) benzoic acid from poly(ethylene terephthalate) plastic waste. CAC 16, 119–137 (2020)

    Article  CAS  Google Scholar 

  57. A.M. Fahim, H.E. Tolan, W.A. El-Sayed, Synthesis of novel 1, 2, 3-triazole based acridine and benzothiazole scaffold N-glycosides with anti-proliferative activity, docking studies, and comparative computational studies. J. Mol. Struct. 1251, 131941 (2021)

    Article  Google Scholar 

  58. A.M. Fahim, H.E. Tolan, H. Awad, E.H. Ismael, Synthesis, antimicrobial and antiproliferative activities, molecular docking, and computational studies of novel heterocycles. J. Iran. Chem. Soc. (2021). https://doi.org/10.1007/s13738-021-02251-7

    Article  Google Scholar 

  59. A.M. Fahim, H.S. Magar, E. Nasar, F.M. Abdelrazek, A. Aboelnaga, Synthesis of Cu-porphyrazines by annulated diazepine rings with electrochemical, conductance activities and computational studies. J. Inorg. Organomet. Polym. Mater. (2021). https://doi.org/10.1007/s10904-021-02122-x

    Article  Google Scholar 

  60. G.H. Elsayed, S. Dacrory, A.M. Fahim, Anti-proliferative action, molecular investigation and computational studies of novel fused heterocyclic cellulosic compounds on human cancer cells, Int. J. Biol. Macromol. 222, Part B, 3077–3099 (2022). https://doi.org/10.1016/j.ijbiomac.2022.10.083

    Article  CAS  Google Scholar 

  61. A.M. Fahim, A.M. Farag, Synthesis, antimicrobial evaluation, molecular docking and theoretical calculations of novel pyrazolo [1, 5-a] pyrimidine derivatives. J. Mol. Struct. 1199, 127025 (2020)

    Article  Google Scholar 

  62. A.M. Fahim, Microwave assisted regioselective synthesis and biological evaluation of Pyrano[2,3-c]Pyridine derivatives utilizing DMAP as a catalyst. OnLine J. Biol. Sci. 17(4), 394–403 (2017). https://doi.org/10.3844/ojbsci.2017.394.403

    Article  Google Scholar 

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Acknowledgements

The authors acknowledge the National Research Center (NRC), Egypt.

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Authors and Affiliations

  1. Department of Green Chemistry, National Research Centre Dokki, P.O. Box.12622, Cairo, Egypt

    Asmaa M. Fahim

  2. Department of Cellulose and Paper, National Research Centre, Giza, 12622, Egypt

    Mohamed Hasanin & Sawsan Dacrory

  3. Microanalysis Laboratory, Applied Organic Chemistry Department, National Research Centre, El-Bohouth St., Dokki, Giza, 12622, Egypt

    I. H. I. Habib & Rehab O. El-Attar

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  1. Asmaa M. Fahim
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Fahim, A.M., Hasanin, M., Habib, I.H.I. et al. Synthesis, antimicrobial activity, theoretical investigation, and electrochemical studies of cellulosic metal complexes. J IRAN CHEM SOC 20, 1699–1718 (2023). https://doi.org/10.1007/s13738-023-02790-1

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