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Synthesis, Physicochemical, and Biological Studies of New Pyridoxine HCl Mononuclear Drug Complexes of V(III), Ru(III), Pt(II), Se(IV), and Au(III) Metal Ions

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Abstract

Pyridoxine HCl (vitamin B6; Pyr-H3) complexes with the formula [M(Pyr-H)(H2O)4].Cl·nH2O [M= V(III), Ru(III); n = 0.1], [Pt(Pyr-H)(H2O)(Cl)].Cl, [Se(Pyr-H3)(O)(OH)2], and [Au(Pyr-H)(H2O)2]·Cl are synthesized by the reactions of Pyr-H3 with metal chlorides [V(III), Ru(III), Pt(II), Se(IV), and Au(III)] at 60°C in methanol–water 50: 50 v/v. The accumulated data of the elemental analysis, conductivity measurements, mass, FT-IR, 1H, and 13C NMR, UV-Vis spectroscopy and magnetic moments support elucidated stoichiometry, structures and chelation of the complexes. Thermogravimetric analysis of the synthesized solid complexes is carried out for determining their thermal stability, number of crystalline water molecules and decomposition steps. According to the physicochemical analyses Pyr-H3 reacts with metal ions as a bidentate ligand via both phenolate oxygen and oxygen of the CH2OH group. The antimicrobial and anticancer tests reveal that complexes demonstrate higher antibacterial activity than free Pyr-H3 chelate. According to the cytotoxic results of Pt(IV) and Au(III) complexes in vitro based on human hepato cellular carcinoma (HepG-2) and human breast cancer (MCF-7) tumor cell lines, the former one exhibits promising activity.

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References

  1. Zaky, M., El-Sayed, M.Y., El-Megharbel, S.M., Abo Taleb, S., and Refat, M.S., Russ. J. Gen. Chem., 2015, vol. 85, p. 176. doi 10.1134/S1070363215010314

    Article  CAS  Google Scholar 

  2. Al-Khodir, F.A.I. and Refat, M.S., Russ. J. Gen. Chem., 2015, vol. 85, p. 718. doi 10.1134/S1070363215030317

    Article  CAS  Google Scholar 

  3. Al-Khodir, F.A.I. and Refat, M.S., Russ. J. Gen. Chem., 2015, vol. 85, p. 1734. doi 10.1134/S1070363215070270

    Article  CAS  Google Scholar 

  4. El-Megharbel, S.M., Adam, A.M.A., Megahed, A.S., and Refat, M.S., Russ. J. Gen. Chem., 2015, vol. 85, p. 2366. doi 10.1134/S1070363215100230

    Article  CAS  Google Scholar 

  5. Al-Khodir, F.A.I. and Refat, M.S., Russ. J. Gen. Chem., 2016, vol. 86, p. 708. doi 10.1134/S1070363216030324

    Article  CAS  Google Scholar 

  6. Chaviara, T., Christidis, P.C., Papageorgiou, A., Chrysogelou, E., Hadjipavlou-Litina, D.J., and Bolos, C.A., J. Inorg. Biochem, 2005, vol. 99, p. 2102. doi 10.1016/j.jinorgbio.2005.07.011

    Article  CAS  PubMed  Google Scholar 

  7. Nakai, M., Sekiguchi, F., Obata, M., Ohtsuki, C., Adachi, Y., Sakurai, H., Orvig, C., Rehder, D., and Yano, S., J. Inorg. Biochem., 2005, vol. 99, p. 1275. doi 10.1016/j.jinorgbio.2005.02.026

    Article  CAS  PubMed  Google Scholar 

  8. Yang, K.W., Wang, L.F., Wu, J., and Yang, Z.Y., J. Inorg. Biochem., 1993, vol. 52, p. 151. doi 10.1016/0162-0134(93)85032-4

    Article  CAS  PubMed  Google Scholar 

  9. Somer, M.A. and Elizabeth, R.D., Food & Mood, Henry Holt and Company, LLC, 1999, p.200.

    Google Scholar 

  10. Fried, B. and Sherma, J., Analysis of Hydrophilic Vitamins, Chromatographic Science Series, vol. 81, New York: Marcel Dekker, 1999, p.215.

    Google Scholar 

  11. Metzler, D.E. and Snell, E.E., J. Am. Chem. Soc., 1955, vol. 77, p. 2431. doi 10.1021/ja01614a022

    Article  CAS  Google Scholar 

  12. Matushima, Y. and Martell, A.E., J. Amer. Chem. Soc., 1967, vol. 89, p. 1322. doi.10.1021/ja00982a008

    Article  Google Scholar 

  13. Lapper, R.D., Manisch, H.H., and Smith, I.C.P., Can. J. Chem., 1975, vol. 53, p. 2406. doi 10.1139/v75-340

    Article  CAS  Google Scholar 

  14. Hanic, F., Acta Crystallogr., 1966, vol. 21, p. 332. doi 10.1107/S0365110X66002895

    Article  CAS  PubMed  Google Scholar 

  15. El-Ezaby, M.S. and El-Eziri, F.R., J. Inorg. Nulc. Chem., 1976, vol. 38, p. 1901. doi 10.1016/0022-1902 (76)80119-4

    Article  CAS  Google Scholar 

  16. Hartman, J.S. and Kelusky, E.C., Can. J. Chem., 1979, vol. 57, p. 2118. doi 10.1139/v79-340

    Article  CAS  Google Scholar 

  17. Mosset, A., Nepveu-Juras, F., Haran, R., and Bonnet, J.J., J. Inorg. Nucl. Chem., 1978, vol. 40, p. 1259. doi 10.1016/0022-1902(78)80550-8

    Article  CAS  Google Scholar 

  18. Eliot, A.C. and Kirsch, J.F., Annu. Rev. Biochem., 2004, vol. 73, p. 383. doi 10.1146/annurev.biochem. 73.011303.074021

    Article  CAS  PubMed  Google Scholar 

  19. Makhyoun, M.A., Al-Salem, N.A., and El-Ezaby, M.S., Inorg. Chim. Acta, 1986, vol. 123, p. 117–125. doi 10.1016/S0020-1693(00)86333-1

    Article  CAS  Google Scholar 

  20. Back, D.F., de Oliveira, G.M., and Lang, E.S., J. Inorg. Biochem., 2006, vol. 100, p. 1698. doi 10.1016/j.jinorgbio.2006.06.004

    Article  CAS  PubMed  Google Scholar 

  21. Bonfada, E., Oliveira, G.M., Back, D.F., and Lang, E.S., Anorg. Allg. Chem., 2005, vol. 631, p. 878. doi 10.1002/zaac.200400504

    Article  CAS  Google Scholar 

  22. Rao, S.P.S., Varughese, K.I., and Manohar, H., Inorg. Chem., 1986, vol. 25, p. 734. doi 10.1021/ic00226a006

    Article  Google Scholar 

  23. Neelakantan, M.A., Sundaram, M., Thalamuthu, S., and Nair, M.S., J. Coord. Chem., 2010, vol. 63, p. 1969. doi 10.1080/00958972.2010.493583

    Article  CAS  Google Scholar 

  24. Casas, J.S., Castineiras, A., Condori, F., Couce, M.D., Russo, U., Sanchez, A., Sordo, J., and Varela, J.M., Polyhedron, 2000, vol. 19, p. 813. doi 10.1016/S0277-5387(00)00321-1

    Article  CAS  Google Scholar 

  25. Mathews, I.I., and Manohar, H., J. Chem. Soc., Dalton Trans., 1991, p. 2139. doi 10.1039/DT9910002139

    Google Scholar 

  26. Chamayou, A.C., Neelakantan, M.A., Thalamuthu, S., and Janiak, C., Inorg. Chim. Acta, 2011, vol. 365, p. 447. doi 10.1016/j.ica.2010.07.033

    Article  CAS  Google Scholar 

  27. Dey, S., Banerjee, P., Gangopadhyay, S., and Vojtísek, P., Trans. Met. Chem., 2003, vol. 28, p. 765. doi 10.1023/A:1026073108597

    Article  CAS  Google Scholar 

  28. Acquaye, J.H.K.A. and Richardson, M.F., Inorg. Chim. Acta, 1992, vol. 201, p. 101. doi 10.1016/S0020-1693 (00)85009-4

    Article  CAS  Google Scholar 

  29. Sabirov, V.Kh., Litvinov, I.A., and Yunuskhodzhaev, A.N., Koord. Khim., 1991, vol. 17, p.44.

    CAS  Google Scholar 

  30. Refat, M.S., Elsabawy, K.M., Alhadhrami, A., Almalki, A.S.A., El-Sayed, M.Y., and Hassan, R.F., J. Mol. Liq., 2018, vol. 255, p. 462. doi 10.1016/j.molliq.2018.01.187

    Article  CAS  Google Scholar 

  31. Abd El-Wahed, M.G., El-Megharbel, S.M., El-Sayed, M.Y., Zahran, Y.M., and Refat, M.S., Russ. J. Gen. Chem., 2016, vol. 86, p. 391–399. doi 10.1134/S1070363216020328

    Article  CAS  Google Scholar 

  32. Al-Khodir, F.A.I. and Refat, M.S., Russ. J. Gen. Chem., 2017, vol. 87, p. 873. doi 10.1134/S107036321704034X

    Article  CAS  Google Scholar 

  33. Al-Khodir, F.A.I. and Refat, M.S., Russ. J. Gen. Chem., 2017, vol. 87, p. 1087. doi 10.1134/S1070363217050322

    Article  CAS  Google Scholar 

  34. Bauer, A.W., Kirby, W.A., Sherris, C., and Turck, M., Am. J. Clin. Pathology, 1996, vol. 45, p.493.

    Article  Google Scholar 

  35. Pfaller, M.A., Burmeister, L., Bartlett, M.A., and Rinaldi, M.G., J. Clin. Microbiol., 1988, vol. 26, p. 1437.

    CAS  PubMed  PubMed Central  Google Scholar 

  36. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, p. 55. doi 10.1016/0022-1759(83)90303-4

    Article  CAS  PubMed  Google Scholar 

  37. Gomha, S.M., Riyadh, S.M., Mahmmoud, E.A., and Elaasser, M.M., Heterocycles, 2015, vol. 91, p. 1227.

    Article  CAS  Google Scholar 

  38. Refat, M.S., J. Mol. Struct., 2007, vol. 842, p. 24. doi 10.1016/j.molstruc.2006.12.006

    Article  CAS  Google Scholar 

  39. Nakamoto, K., Infrared and Raman Spectra of Inorganic and Coordination Compounds, New York: Wiley, 1997.

    Google Scholar 

  40. Ross, S.D., Inorganic Infrared and Raman Spectra, London: Mc Graw Hill, 1972.

    Google Scholar 

  41. Drago, R.S., Physical Methods in Chemistry, Philadelphia: W.B. Saunders, 1977, p.382.

    Google Scholar 

  42. Podsiadly, H. and Karwecka, Z., Polyhedron, 2009, vol. 28, p. 1568. doi 10.1016/j.poly.2009.03.015

    Article  CAS  Google Scholar 

  43. Chandra, S., Synth. React. Inorg. Met.-Org., Nano-Met. Chem., 1992, vol. 22, p. 1565. doi 10.1080/15533179208020277

    Article  Google Scholar 

  44. Lever, A.B.P., Inorganic Electronic Spectroscopy, Elsevier, 1984.

    Google Scholar 

  45. Oliff, R.W. and Odell, A.L., J. Chem. Soc., 1964, p. 2467. doi 10.1039/JR9640002417

    Google Scholar 

  46. Tunney, J.M., Blake, A.J., Davies, E.S., Mcmater, J., Wilson, C., and Garner, C.D., Polyhedron, 2006, vol. 25, p. 591. doi 10.1016/j.poly.2005.09.002

    Article  CAS  Google Scholar 

  47. Llor, J. and Munoz, L., J. Org. Chem., 2000, vol. 65, p. 2716. doi 10.1021/jo991821t

    Article  CAS  PubMed  Google Scholar 

  48. Horowitz, H.H., and Metzger, G., Analytical Chemistry, 1963, vol. 35, p. 1464. doi. 10.1021/ac60203a013

    Article  CAS  Google Scholar 

  49. Coats, A.W. and Redfern, J.P., Nature, 1964, vol. 201, p. 68. doi 10.1002/pol.1965.110031106

    Article  CAS  Google Scholar 

  50. X-Ray Diffraction Procedures for Polycrystalline and Amorphous Materials, Klug, H.P., Ed., New York: Wiley, 1974.

  51. Miyauchi, A., and Okabe, T.H., Materials Transactions, 2010, vol. 51, p. 1102. doi 10.2320/matertrans.M2010027

    Article  CAS  Google Scholar 

  52. Singh, J.P., Karabacak, T., Morrow, P., Pimanpang, S., Lu, T.-M., and Wang, G.-C., J. Nanosci. Nanotechnol., 2007, vol. 7, p. 2192. doi 10.1166/jnn.2007.793

    Article  CAS  PubMed  Google Scholar 

  53. Krehula, S. and Music, S., Croat. Chem. Acta, 2011, vol. 84, p.465.

    Article  CAS  Google Scholar 

  54. Dwivedi, S., AlKhedhairy, A.A., Ahamed, M., and Musarrat, J., PLoS One, 2013, vol. 8, p. e57404. doi 10.1371/journal.pone.0057404

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. He, S., Guo, Z., Zhang, Y., Zhang, S., Wang, J., and Gu, N., Mater. Lett., 2007, vol. 61, p. 3984. doi 10.1016/j.matlet.2007.01.018

    Article  CAS  Google Scholar 

  56. Tabassum, S., Asim, A., Arjmand, F., Arjmand, F., Afzal, M., and Bagchi, V., Eur. J. Med. Chem., 2012, vol. 58, p. 308. doi 10.1016/j.ejmech.2012.09.051

    Article  CAS  PubMed  Google Scholar 

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Alibrahim, K.A., Al-Saif, F.A., Bakhsh, H.A. et al. Synthesis, Physicochemical, and Biological Studies of New Pyridoxine HCl Mononuclear Drug Complexes of V(III), Ru(III), Pt(II), Se(IV), and Au(III) Metal Ions. Russ J Gen Chem 88, 2400–2409 (2018). https://doi.org/10.1134/S1070363218110245

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