Investigation of microwave assisted synthesis of Schiff Base derived Metal-Chelates by liquid invert sugar containing D-Glucose

References

• Bagherzadeh, M.; Amini, M.; Derakhshandeh, P. G.; Haghdoost, M. M. An Efficient Glucose-Based Ligand for Heck and Suzuki Coupling Reactions in Aqueous Media. J. Iran. Chem. Soc. 2014, 11, 441–446. DOI: 10.1007/s13738-013-0316-3.
   Google Scholar
• Dallinger, D.; Kappe, C. O. Microwave-Assisted Synthesis in Water as Solvent. Chem. Rev. 2007, 107, 2563–2591. DOI: 10.1021/cr0509410.
   PubMed Web of Science ®Google Scholar
• Thakur, K. G.; Ganapathy, D.; Sekar, G. D-Glucosamine as a Green Ligand for Copper Catalyzed Synthesis of Primary Aryl Amines from Aryl Halides and Ammonia. Chem Commun. (Camb) 2011, 47, 5076–5078. DOI: 10.1039/C1CC10568J.
   PubMed Web of Science ®Google Scholar
• Sheldon, R. A. Green Solvents for Sustainable Organic Synthesis: State of the Art. Green Chem. 2005, 7, 267–278. DOI: 10.1039/b418069k.
   Web of Science ®Google Scholar
• Thornalley, P. J.; Langborg, A.; Minhas, H. S. Formation of Glyoxal, Methylglyoxal and 3-Deoxyglucosone in the Glycation of Proteins by Glucose. Biochem. J. 1999, 344, 109–116. DOI: 10.1042/bj3440109.
   PubMed Web of Science ®Google Scholar
• Watkins, N. G.; Thorpe, S. R.; Baynes, J. W. Glycation of Amino-Groups in Protein - Studies on the Specificity of Modification of Rnase by Glucose. J. Biol. Chem. 1985, 260, 629–636. DOI: 10.1016/S0021-9258(19)85131-1.
   Google Scholar
• Venkatraman, J.; Aggarwal, K.; Balaram, P. Helical Peptide Models for Protein Glycation: Proximity Effects in Catalysis of the Amadori Rearrangement. Chem. Biol. 2001, 8, 611–625. DOI: 10.1016/S1074-5521(01)00036-9.
   PubMedGoogle Scholar
• Shakkottai, V. G.; Sudha, R.; Balaram, P.; Gramicidin, S. A Peptide Model for Protein Glycation and Reversal of Glycation Using Nucleophilic Amines. J. Pept. Res. 2002, 60, 112–120. DOI: 10.1034/j.1399-3011.2002.02901.x.
   PubMedGoogle Scholar
• John, W. G.; Lamb, E. J. The Maillard or Browning Reaction in Diabetes. Eye 1993, 7, 230–237. DOI: 10.1038/eye.1993.55.
   PubMed Web of Science ®Google Scholar
• Wang, Y.; Ho, C. T. Flavour Chemistry of Methylglyoxal and Glyoxal. Chem. Soc. Rev. 2012, 41, 4140–4149. DOI: 10.1039/c2cs35025d.
   PubMed Web of Science ®Google Scholar
• Reyes, F. G. R.; Poocharoen, B.; Wrolstad, R. E. Maillard Browning Reaction of Sugar-Glycine Model Systems-Changes in Sugar Concentration, Color and Appearance. J. Food Sci. 1982, 47, 1376–1377. DOI: 10.1111/j.1365-2621.1982.tb07690.x.
   Google Scholar
• Jalbout, A. F.; Shipar, M. A. H.; Navarro, J. L. Density Functional Computational Studies on Ribose and Glycine Maillard Reaction: Formation of the Amadori Rearrangement Products in Aqueous Solution. Food Chem. 2007, 103, 919–926. DOI: 10.1016/j.foodchem.2006.09.045.
   Google Scholar
• Kaufmann, M.; Mugge, C.; Kroh, L. W. NMR Analyses of Complex D-Glucose Anomerization. Food Chem. 2018, 265, 222–226. DOI: 10.1016/j.foodchem.2018.05.100.
   PubMedGoogle Scholar
• Jakus, V.; Rietbrock, N. Advanced Glycation End-Products and the Progress of Diabetic Vascular Complications. Physiol. Res. 2004, 53, 131–142.
   PubMed Web of Science ®Google Scholar
• Dhar, D. N.; Taploo, C. L. Schiff-Bases and Their Applications. J. Sci. Ind. Res. 1982, 41, 501–506.
   Web of Science ®Google Scholar
• Przybylski, P.; Huczynski, A.; Pyta, K.; Brzezinski, B.; Bartl, F. Biological Properties of Schiff Bases and Azo Derivatives of Phenols. COC. 2009, 13, 124–148. DOI: 10.2174/138527209787193774.
   Web of Science ®Google Scholar
• Brown, S. B.; Bowes, M. A. Glycosylated Hemoglobins and Their Role in Management of Diabetes-Mellitus. Biochem. Educ. 1985, 13, 2–6. DOI: 10.1016/0307-4412(85)90112-8.
   Google Scholar
• Arslaner, C.; Karakurt, S.; Koc, Z. E. Synthesis of Benzimidazole Schiff Base Derivatives and Cytotoxic Effects on Colon and Cervix Cancer Cell Lines. Biointerface Res. Appl. Chem. 2017, 7, 2103–2107.
   Google Scholar
• Koc, Z. E.; Aladag, M. O.; Uysal, A. Synthesis of Novel Dopamine Derived Multidirectional Ligands from Cyanuric Chloride: Structural and Antimicrobial Studies. Excli J. 2013, 12, 396–403. DOI: 10.17877/DE290R-10849.
   PubMed Web of Science ®Google Scholar
• Safoura, F. Novel Synthesis of Schiff Bases Bearing Glucosamine Moiety Res. J. Chem. Sci 2014, 4, 25–28.
   Google Scholar
• Sah, A. K.; Rao, C. P.; Saarenketo, P. K.; Kolehmainen, E.; Rissanen, K. Synthesis, Characterisation and Crystal Structures of Schiff Bases from the Reaction of 4,6-O-Ethylidene-Beta-D-Glucopyranosylamine with Substituted Salicylaldehydes. Carbohydr. Res. 2001, 335, 33–43. DOI: 10.1016/s0008-6215(01)00201-4.
   PubMed Web of Science ®Google Scholar
• Costamagna, J.; Lillo, L. E.; Matsuhiro, B.; Noseda, M. D.; Villagran, M. Ni(II) Complexes with Schiff Bases Derived from Amino Sugars. Carbohydr. Res. 2003, 338, 1535–1542. DOI: 10.1016/s0008-6215(03)00237-4.
   PubMed Web of Science ®Google Scholar
• Tanase, T.; Mano, K.; Yamamoto, Y. Synthesis and Characterization of Copper(II) Complexes Containing N-Glycoside Ligands and Their Use in the Catalytic Epoxidation of Olefins. Inorg. Chem. 1993, 32, 3995–4003. DOI: 10.1021/ic00071a007.
   Web of Science ®Google Scholar
• Perez, E. M. S.; Avalos, M.; Babiano, R.; Cintas, P.; Light, M. E.; Jimenez, J. L.; Palacios, J. C.; Sancho, A. Schiff Bases from D-Glucosamine and Aliphatic Ketones. Carbohydr. Res. 2010, 345, 23–32. DOI: 10.1016/j.carres.2009.08.032.
   PubMed Web of Science ®Google Scholar
• Higgins, P. J.; Bunn, H. F. Kinetic-Analysis of the Non-Enzymatic Glycosylation of Hemoglobin. J. Biol. Chem. 1981, 256, 5204–5208. DOI: 10.1016/S0021-9258(19)69387-7.
   PubMed Web of Science ®Google Scholar
• Pessoa, J. C.; Tomaz, I.; Henriques, R. T. Preparation and Characterisation of Vanadium Complexes Derived from Salicylaldehyde or Pyridoxal and Sugar Derivatives. Inorg. Chim. Acta 2003, 356, 121–132. DOI: 10.1016/S0020-1693(03)00395-5.
   Web of Science ®Google Scholar
• Tsubomura, T.; Yano, S.; Toriumi, K.; Ito, T.; Yoshikawa, S. Reactions of Metal-Complexes with Carbohydrates - Synthesis and Structure of (2-[(2-Aminoethyl)Amino]-2-deoxy-L-Sorbose)(Ethylenediamine)Nickel(II)Dichloride Hemi Methanol Solvate- [Ni(en)(L-Sor-en)]Cl2.1/2CH3OH (en = Ethylenediamine and Sor = Sorbose). BCSJ. 1984, 57, 1833–1838. DOI: 10.1246/bcsj.57.1833.
   Google Scholar
• Clark, S. L. D.; Santin, A. E.; Bryant, P. A.; Holman, R. W.; Rodnick, K. J. The Initial Noncovalent Binding of Glucose to Human Hemoglobin in Nonenzymatic Glycation. Glycobiology 2013, 23, 1250–1259. DOI: 10.1093/glycob/cwt061.
   PubMed Web of Science ®Google Scholar
• Adam, M. J.; Hall, L. D. Synthesis of Metal-Chelates of Amino Sugars: Schiff’s Base Complexes. Can. J. Chem. 1982, 60, 2229–2237. DOI: 10.1139/v82-317.
   Web of Science ®Google Scholar
• Hedegaard, R. V.; Frandsen, H.; Skibsted, L. H. Kinetics of Formation of Acrylamide and Schiff Base Intermediates from Asparagine and Glucose. Food Chem. 2008, 108, 917–925. DOI: 10.1016/j.foodchem.2007.11.073.
   PubMedGoogle Scholar
• Hijji, Y.; Rajan, R.; Ben Yahia, H.; Mansour, S.; Zarrouk, A.; Warad, I. One-Pot Microwave-Assisted Synthesis of Water-Soluble Pyran-2,4,5-Triol Glucose Amine Schiff Base Derivative: XRD/HSA Interactions, Crystal Structure, Spectral, Thermal and a DFT/TD-DFT. Cryst 2021, 11, 117. DOI: 10.3390/cryst11020117.
   Google Scholar
• Kołodziej, B.; Grech, E.; Schilf, W.; Kamieński, B.; Makowski, M.; Rozwadowski, Z.; Dziembowska, T. Anomeric and Tautomeric Equilibria in D-2-Glucosamine Schiff Bases. J. Mol. Struct. 2007, 844-845, 32–37. DOI: 10.1016/j.molstruc.2007.07.038.
   Web of Science ®Google Scholar
• Xing, H. R.; Mossine, V. V.; Yaylayan, V. Diagnostic MS/MS Fragmentation Patterns for the Discrimination between Schiff Bases and Their Amadori or Heyns Rearrangement Products. Carbohydr. Res. 2020, 491, 107985. DOI: 10.1016/j.carres.2020.107985.
   PubMedGoogle Scholar
• Naz, N.; Khatoon, S.; Ajaz, H.; Sadiq, Z.; Iqbal, M. Z. Synthesis, Spectral Characterization and Biological Evaluation of Schiff Base Transition Metal Complexes Derived from Ampicillin with D-Glucose. Asian J. Chem. 2013, 25, 2239–2242. DOI: 10.14233/ajchem.2013.13413.
   Google Scholar
• Das, K.; Datta, A.; Roy, S.; Clegg, J. K.; Garribba, E.; Sinha, C.; Kara, H. Doubly Phenoxo-Bridged M-Na (M = Cu(II), Ni(II)) Complexes of Tetradentate Schiff Base: Structure, Photoluminescence, EPR, Electrochemical Studies and DFT Computation. Polyhedron 2014, 78, 62–71. DOI: 10.1016/j.poly.2014.04.032.
   Google Scholar
• Donmez, A.; Oylumluoglu, G.; Coban, M. B.; Kocak, C.; Aygun, M.; Kara, H. Ferromagnetic Interactions in New Double End-On-Azide-Bridged Dinuclear Ni(II) Complex: Synthesis, Crystal Structures, Magnetic and Photoluminescence Properties. J. Mol. Struct. 2017, 1149, 569–575. DOI: 10.1016/j.molstruc.2017.08.027.
   Web of Science ®Google Scholar
• Gungor, E.; Kara, H.; Colacio, E.; Mota, A. J. Two Tetranuclear Copper(II) Complexes with Open Cubane-Like Cu4O4 Core Framework and Ferromagnetic Exchange Interactions between Copper(II) Ions: Structure, Magnetic Properties, and Density Functional Study. Eur. J. Inorg. Chem. 2014, 2014, 1552–1560. DOI: 10.1002/ejic.201301515.
   Web of Science ®Google Scholar
• Majumder, I.; Chakraborty, P.; Adhikary, J.; Kara, H.; Zangrando, E.; Bauza, A.; Frontera, A.; Das, D. Auxiliary Part of Ligand Mediated Unique Coordination Chemistry of Copper (II). Chemistryselect 2016, 1, 615–625. DOI: 10.1002/slct.201500030.
   Google Scholar
• Li, S. M.; Liu, S. Y.; Ho, C. T. Safety Issues of Methylglyoxal and Potential Scavengers. Front. Agr. Sci. Eng. 2018, 5, 312–320. DOI: 10.15302/J-FASE-2017174.
   Google Scholar
• Curtiss, L. K.; Witztum, J. L. A Novel Method for Generating Region-Specific Monoclonal-Antibodies to Modified Proteins-Application to the Identification of Human Glucosylated Low-Density Lipoproteins. J. Clin. Invest. 1983, 72, 1427–1438. DOI: 10.1172/JCI111099.
   PubMedGoogle Scholar
• Al-Abed, Y.; Mitsuhashi, T.; Li, H. W.; Lawson, J. A.; FitzGerald, G. A.; Founds, H.; Donnelly, T.; Cerami, A.; Ulrich, P.; Bucala, R. Inhibition of Advanced Glycation Endproduct Formation by Acetaldehyde: Role in the Cardioprotective Effect of Ethanol. Proc. Natl. Acad. Sci. U S A 1999, 96, 2385–2390. DOI: 10.1073/pnas.96.5.2385.
   PubMed Web of Science ®Google Scholar
• Harohally, N. V.; Srinivas, S. M.; Umesh, S. ZnCl2-Mediated Practical Protocol for the Synthesis of Amadori Ketoses. Food Chem. 2014, 158, 340–344. DOI: 10.1016/j.foodchem.2014.02.094.
   PubMed Web of Science ®Google Scholar
• Celik, S. C.; Vatansev, H.; Koc, Z. E, Department of Clinical Immunology and Allergy, Meram Faculty of Medicine, Necmettin Erbakan University, Konya 42090, Turkey Benzimidazole Schiff Bases Microwave Assisted Synthesis and the Effect on Leukemia Cells with Flow Cytometry. Rev. Roum. Chim. 2019, 64, 615–623. DOI: 10.33224/rrch/2019.64.7.08.
   Google Scholar
• Koc, Z. E.; Ucan, H. I. Complexes of Iron(III) and Chrom(III) Salen and Saloph Schiff Bases with Bridging 2,4,6-Tris(4-Nitrophenylimino-4'-Formylphenoxy)-1,3,5-Triazine. J. Macromol. Sci. A 2008, 45, 1074–1079. DOI: 10.1080/10601320802458087.
   Google Scholar
• Uysal, S.; Koc, Z. E. The Synthesis and Characterization of (MSalen/Salophen/Saldeta/Salpy) [M = Fe(III) or Cr(III)] Capped Heteromultinuclear Schiff Bases-Dioxime Ni(II) Complexes: Their Thermal and Magnetic Behaviours. J. Mol. Struct. 2018, 1165, 14–22. DOI: 10.1016/j.molstruc.2018.03.101.
   Web of Science ®Google Scholar
• Koc, Z. E.; Uysal, S. Synthesis and Characterization of Dendrimeric Bridged Salen/Saloph Complexes and Investigation of Their Magnetic and Thermal Behaviors. HCA. 2010, 93, 910–919. DOI: 10.1002/hlca.200900294.
   Web of Science ®Google Scholar
• Koc, Z. E.; Ucan, H. I. Complexes of Iron(III) Salen and Saloph Schiff Bases with Bridging 2,4,6-Tris(2,5-Dicarboxyphenylimino-4-Formylphenoxy)-1,3,5-Triazine and 2,4,6-Tris(4-Carboxyphenylimino-4'-Formylphenoxy)-1,3,5-Triazine. Transition Met. Chem. 2007, 32, 597–602. DOI: 10.1007/s11243-007-0213-7.
   Web of Science ®Google Scholar
• Celikbilek, S.; Koc, Z. E. Investigation of Dipodal Oxy-Schiff Base and Its Salen and Salophen Fe(III)/Cr(III)/Mn(III) Schiff Bases (N2O2) Caped Complexes and Their Magnetic and Thermal Behaviors. J. Mol. Struct. 2014, 1065-1066, 205–209. DOI: 10.1016/j.molstruc.2014.03.003.
   Web of Science ®Google Scholar
• Uysal, S.; Koc, Z. E.; Celikbilek, S.; Ucan, H. I. Synthesis of Star-Shaped Macromolecular Schiff Base Complexes Having Melamine Cores and Their Magnetic and Thermal Behaviors. Synth. Commun. 2012, 42, 1033–1044. DOI: 10.1080/00397911.2010.535635.
   Web of Science ®Google Scholar
• Koc, Z. E.; Uysal, S. Synthesis and Characterization of Tripodal Oxy-Schiff Base (2,4,6-Tris(4-Carboxymethylenephenylimino-4'-Formylphenoxy)-1,3,5-Triazine) and the Thermal and Magnetic Properties of Its Fe(III)/Cr(III) Complexes. J. Inorg. Organomet. Polym. 2011, 21, 400–406. DOI: 10.1007/s10904-011-9475-9.
   Web of Science ®Google Scholar
• Uysal, S.; Koc, Z. E. Synthesis and Characterization of Dendrimeric Melamine Cored [Salen/salophFe(III)] and [Salen/SalophCr(III)] Capped Complexes and Their Magnetic Behaviors. J. Hazard. Mater. 2010, 175, 532–539. DOI: 10.1016/j.jhazmat.2009.10.038.
   PubMed Web of Science ®Google Scholar
• Uysal, S.; Koc, Z. E. Synthesis and Characterization of Dopamine Substitue Tripodal Trinuclear [(Salen/Salophen/Salpropen)M] (M = Cr(III), Mn(III), Fe(III) Ions) Capped s-Triazine Complexes: Investigation of Their Thermal and Magnetic Properties. J. Mol. Struct 2016, 1109, 119–126. DOI: 10.1016/j.molstruc.2015.12.080.
   Web of Science ®Google Scholar