Calcium(II)–naproxen complex: Synthesis, characterization, and interaction with human serum albumin

References

• Schoen, R. T.; Vender, R. J. Mechanisms of nonsteroidal anti-inflammatory drug-induced gastric damage. The American Journal of Medicine 1989, 86(4), 449–458.
   PubMed Web of Science ®Google Scholar
• Etcheverry, S.; Barrio, D.; Cortizo, A.; Williams, P. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. Journal of Inorganic Biochemistry 2002, 88(1), 94–100.
   PubMed Web of Science ®Google Scholar
• Abuhijleh, A. L.; Khalaf, J. Copper(II) complexes of the anti-inflammatory drug naproxen and 3-pyridylmethanol as auxiliary ligand. Characterization, superoxide dismutase and catecholase–mimetic activities. European Journal of Medicinal Chemistry 2010, 45(9), 3811–3817.
   PubMed Web of Science ®Google Scholar
• Dimiza, F.; Papadopoulos, A. N.; Tangoulis, V.; Psycharis, V.; Raptopoulou, C. P.; Kessissoglou, D. P.; Psomas, G. Biological evaluation of cobalt(II) complexes with non-steroidal anti-inflammatory drug naproxen. Journal of Inorganic Biochemistry 2012, 107(1), 54–64.
   PubMed Web of Science ®Google Scholar
• Ali, H. A.; Fares, H.; Darawsheh, M.; Rappocciolo, E.; Akkawi, M.; Jaber, S. Synthesis, characterization and biological activity of new mixed ligand complexes of Zn(II) naproxen with nitrogen based ligands. European Journal of Medicinal Chemistry 2015, 89, 67–76.
   PubMed Web of Science ®Google Scholar
• Sharma, J.; Singla, A. K.; Dhawan, S. Zinc–naproxen complex: Synthesis, physicochemical and biological evaluation. International Journal of Pharmaceutics 2003, 260(2), 217–227.
   PubMed Web of Science ®Google Scholar
• Friščić, T.; Halasz, I.; Strobridge, F. C.; Dinnebier, R. E.; Stein, R. S.; Fábián, L.; Curfs, C. A rational approach to screen for hydrated forms of the pharmaceutical derivative magnesium naproxen using liquid-assisted grinding. CrystEngComm 2011, 13(9), 3125–3129.
   Web of Science ®Google Scholar
• Ayub, K.; Hallett, M. B. Ca2+ influx shutdown during neutrophil apoptosis: Importance and possible mechanism. Immunology 2004, 111(1), 8–12.
   PubMed Web of Science ®Google Scholar
• Nazıroğlu, M. New molecular mechanisms on the activation of TRPM2 channels by oxidative stress and ADP-ribose. Neurochemical Research 2007, 32(11), 1990–2001.
   PubMed Web of Science ®Google Scholar
• Fiedoruk-Pogrebniak, M.; Koncki, R. Multicommutated flow analysis system based on fluorescence microdetectors for simultaneous determination of phosphate and calcium ions in human serum. Talanta 2015, 144, 184–188.
   PubMed Web of Science ®Google Scholar
• Franson, R.; Eisen, D.; Jesse, R.; Lanni, C. Inhibition of highly purified mammalian phospholipases A2 by non-steroidal anti-inflammatory agents. Modulation by calcium ions. Biochemical Journal 1980, 186, 633–636.
   PubMed Web of Science ®Google Scholar
• Salgueiro-Pagadigorria, C. L.; Kelmer-Bracht, A. M.; Bracht, A.; Ishii-Iwamoto, E. L. Naproxen affects Ca2+ fluxes in mitochondria, microsomes and plasma membrane vesicles. Chemico-Biological Interactions 2004, 147(1), 49–63.
   PubMed Web of Science ®Google Scholar
• Wu, D.; Du, B.; Ma, H.; Wei, Q.; Xu, G. Quenching of the intrinsic fluorescence of human serum albumin by trimethoxyphenylfluorone–Mo (VI) complex. Spectroscopy Letters 2006, 39(4), 399–408.
   Web of Science ®Google Scholar
• Fanali, G.; di Masi, A.; Trezza, V.; Marino, M.; Fasano, M.; Ascenzi, P. Human serum albumin: From bench to bedside. Molecular Aspects of Medicine 2012, 33(3), 209–290.
   PubMed Web of Science ®Google Scholar
• Cheruvallath, V.; Riley, C.; Narayanan, S.; Lindenbaum, S.; Perrin, J. A quantitative circular dichroic investigation of the binding of the enantiomers of ibuprofen and naproxen to human serum albumin. Journal of Pharmaceutical and Biomedical Analysis 1997, 15(11), 1719–1724.
   PubMed Web of Science ®Google Scholar
• Lammers, I.; Lhiaubet-Vallet, V.; Ariese, F.; Miranda, M. A.; Gooijer, C. Binding of naproxen enantiomers to human serum albumin studied by fluorescence and room-temperature phosphorescence. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013, 105, 67–73.
   PubMed Web of Science ®Google Scholar
• Ràfols, C.; Zarza, S.; Bosch, E. Molecular interactions between some non-steroidal anti-inflammatory drugs (NSAIDs) and bovine (BSA) or human (HSA) serum albumin estimated by means of isothermal titration calorimetry (ITC) and frontal analysis capillary electrophoresis (FA/CE). Talanta 2014, 130, 241–250.
   PubMed Web of Science ®Google Scholar
• Dimiza, F.; Perdih, F.; Tangoulis, V.; Turel, I.; Kessissoglou, D. P.; Psomas, G. Interaction of copper(II) with the non-steroidal anti-inflammatory drugs naproxen and diclofenac: Synthesis, structure, DNA-and albumin-binding. Journal of Inorganic Biochemistry 2011, 105(3), 476–489.
   PubMed Web of Science ®Google Scholar
• Lin, S. Y.; Li, M. J.; Wei, Y. S. Ethanol or/and captopril-induced precipitation and secondary conformational changes of human serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2004, 60(13): 3107–3111.
   PubMed Web of Science ®Google Scholar
• Wang, J.; Wu, D.; Li, S. S.; Tang, P. X.; Wang, L. L.; Li, H. X-ray powder diffraction data for calcium(II)–naproxen complex (C28H26CaO6 · 2H2O). Powder Diffraction 2015, 30(2), 185–187.
   Web of Science ®Google Scholar
• Kim, Y. B.; Park, I. Y.; Lah, W. R. The crystal structure of naproxen sodium (C14H13O3Na), a non-steroidal antiinflammatory agent. Archives of Pharmacal Research 1990, 13(2), 166–173.
   Google Scholar
• Deák, A.; Tárkányi, G. Chiral self-assembly of methyltin(IV)-naproxenates: Combining dative Sn–O bonds, secondary Sn⋯O interactions and C–H⋯O hydrogen bonding to make an inter-helical meander-shaped network and a cross-linked Z-shaped ribbon. Journal of Organometallic Chemistry 2006, 691(8), 1693–1702.
   Web of Science ®Google Scholar
• Pu, H.; Jiang, H.; Chen, R. Combined multispectroscopic and molecular docking investigation on the interaction between strictosamide and human serum albumin. Luminescence 2013, 28(4), 482–489.
   PubMed Web of Science ®Google Scholar
• Deng, F.; Dong, C.; Liu, Y.; Yu, Y. Study on the interaction between trimethoprim and human serum albumin by spectroscopic and molecular modeling methods. Spectroscopy Letters 2013, 46(1), 13–20.
   Web of Science ®Google Scholar
• Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer Science & Business Media Press: New York, USA, 2013; 11 pp.
   Google Scholar
• Zhang, Y. Z.; Dai, J.; Zhang, X. P.; Yang, X.; Liu, Y. Studies of the interaction between Sudan I and bovine serum albumin by spectroscopic methods. Journal of Molecular Structure 2008, 888(1), 152–159.
   Web of Science ®Google Scholar
• Zeng, H. J.; Qi, T.; Yang, R.; You, J.; Qu, L. B. Spectroscopy and molecular docking study on the interaction behavior between nobiletin and pepsin. Journal of Fluorescence 2014, 24(4), 1031–1040.
   PubMed Web of Science ®Google Scholar
• Hu, Y. J.; Liu, Y.; Xiao, X. H. Investigation of the interaction between berberine and human serum albumin. Biomacromolecules 2009, 10(3), 517–521.
   PubMed Web of Science ®Google Scholar
• Zhang, Y. Z.; Xiang, X.; Mei, P.; Dai, J.; Zhang, L. L.; Liu, Y. Spectroscopic studies on the interaction of Congo Red with bovine serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2009, 72(4), 907–914.
   PubMed Web of Science ®Google Scholar
• Li, X. G.; Wang, S. Study on the interaction of (+)-catechin with human serum albumin using isothermal titration calorimetry and spectroscopic techniques. New Journal Chemistry 2015, 39, 386–395.
   Web of Science ®Google Scholar
• Clegg, R. M. Fluorescence resonance energy transfer. Current Opinion in Biotechnology 1995, 6(1), 103–110.
   PubMedGoogle Scholar
• Li, J.; Li, J.; Jiao, Y.; Dong, C. Spectroscopic analysis and molecular modeling on the interaction of jatrorrhizine with human serum albumin (HSA). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2014, 118, 48–54.
   PubMed Web of Science ®Google Scholar
• Wu, Q.; Jiang, F.; Li, C.; Hu, Y.; Liu, Y. Interaction of caffeine with bovine serum albumin: Determination of binding constants and the binding site by spectroscopic methods. Chinese Journal of Chemistry 2011, 29(3), 433–440.
   Web of Science ®Google Scholar
• Zhang, G.; Ma, Y.; Wang, L.; Zhang, Y.; Zhou, J. Multispectroscopic studies on the interaction of maltol, a food additive, with bovine serum albumin. Food Chemistry 2012, 133(2), 264–270.
   PubMed Web of Science ®Google Scholar
• Fu, L.; Liu, X. F.; Zhou, Q. X.; Zhang, J. X.; Dong, J. Y.; Wang, J. F. Characterization of the interactions of human serum albumin (HSA), gatifloxacin, and metronidazole using spectroscopic and electrochemical methods. Journal of Luminescence 2014, 149, 208–214.
   Web of Science ®Google Scholar
• Peters, T.Jr All About Albumin: Biochemistry, Genetics, and Medical Applications; Academic Press: San Diego, USA, 1995; 79 pp.
   Google Scholar