2-Chloro-1,4-naphthoquinone derivative of quercetin as an inhibitor of aldose reductase and anti-inflammatory agent

References

• Ramana K-V. Aldose reductase: new insights for an old enzyme. Biomol Concepts 2011;2:103–14
   PubMedGoogle Scholar
• Chatzopoulou M, Pegklidou K, Papastavrou N, Demopoulos V-J. Development of aldose reductase inhibitors for the treatment of inflammatory disorders. Expert Opin Drug Discov 2013;8:1365–80
   PubMed Web of Science ®Google Scholar
• Hotta N. New approaches for treatment in diabetes: aldose reductase inhibitors. Biomed Pharmacother 1995;5:244–50
   Google Scholar
• Costantino L, Rastelli G, Gamberini M-C, Barlocco D. Pharmacological approaches to the treatment of diabetic complications. Expert Opin Ther Patents 2000;10:1245–62
   Web of Science ®Google Scholar
• Miyamoto S. Recent advances in aldose reductase inhibitors: potential agents for the treatment of diabetic complications. Expert Opin Ther Patents 2002;12:621–31
   Web of Science ®Google Scholar
• Srivastava S-K, Ramana K-V, Bhatnagar A. Role of aldose reductase and oxidative damage in diabetes and the consequent potential for therapeutic options. Endocr Rev 2005;26:380–92
   PubMed Web of Science ®Google Scholar
• Alexiou P, Pegklidou K, Chatzopoulou M, et al. Aldose reductase enzyme and its implication to major health problems of the 21(st) century. Curr Med Chem 2009;16:734–52
   PubMed Web of Science ®Google Scholar
• Chatzopoulou M, Alexiou P, Kotsampasakou E, Demopoulos V-J. Novel aldose reductase inhibitors: a patent survey (2006-present). Expert Opin Ther Pat 2012;11:1303–23
   Google Scholar
• Boots A-W, Haenen GRMM, Bast A. Health effects of quercetin: from antioxidant to nutraceutical. Eur J Pharm 2008;585:325–37
   PubMed Web of Science ®Google Scholar
• Stefek M, Karasu C. Eye lens in aging and diabetes: effect of quercetin. Rejuvenation Res 2011;14:525–34
   PubMed Web of Science ®Google Scholar
• Arts IC, Sesink A-L, Faassen-Peters M, Hollman P-C. The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides. Br J Nutr 2004;91:841–7
   PubMed Web of Science ®Google Scholar
• Crozier A, Del Rio D, Clifford M-N. Bioavailability of dietary flavonoids and phenolic compounds. Mol Aspects Med 2010;31:446–67
   PubMed Web of Science ®Google Scholar
• Veverka M, Gallovic J, Svajdlenka E, et al. Novel quercetin derivatives: synthesis and screening for antioxidant activity and aldose reductase inhibition. Chem Papers 2013;67:76–83
   Web of Science ®Google Scholar
• Milackova I, Kovacikova L, Veverka M, et al. Screening for antiradical efficiency of 21 semi-synthetic derivatives of quercetin in a DPPH assay. Interdiscip Toxicol 2013;6:13--17
   PubMedGoogle Scholar
• Munday R, Fowke E-A, Smith B-L, Munday C-M. Comparative toxicity of alkyl-1,4-naphthoquinones in rats: relationship to free radical production in vitro. Free Radic Biol Med 1994;16:725–31
   PubMed Web of Science ®Google Scholar
• Munday R, Smith B-L, Munday C-M. Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone. J Appl Toxicol 2007;27:262–9
   PubMed Web of Science ®Google Scholar
• Hayman S, Kinoshita J. Isolation and properties of lens aldose reductase. J Biol Chem 1965;240:877–82
   PubMed Web of Science ®Google Scholar
• Stefek M, Snirc V, Djoubissie P-O, et al. Carboxymethylated pyridoindole antioxidants as aldose reductase inhibitors: synthesis, activity, partitioning, and molecular modelling. Bioorg Med Chem 2008;16:4908–20
   PubMed Web of Science ®Google Scholar
• Costantino L, Rastelli G, Gamberini M-C, et al. 1-Benzopyran-4-one antioxidants as aldose reductase inhibitors. J Med Chem 1999;42:1881–93
   PubMed Web of Science ®Google Scholar
• Juskova M, Snirc V, Gajdosikova A, et al. Carboxymethylated tetrahydropyridoindoles as aldose reductase inhibitors: in vitro selectivity study in intact rat erythrocytes in relation to glycolytic pathway. Gen Physiol Biophys 2009;28:325–30
   PubMed Web of Science ®Google Scholar
• Mylari B-L, Armento S-J, Beebe D-A, et al. A highly selective, non-hydantoin, non-carboxylic acid inhibitor of aldose reductase with potent oral activity in diabetic rat models: 6-(5-chloro-3-methylbenzofuran-2-sulfonyl)-2-H-pyridazin-3-one. J Med Chem 2003;46:2283–6
   PubMed Web of Science ®Google Scholar
• Fabia R, Willen R, Ar’Rajab A, et al. Acetic acid-induced colitis in the rat: a reproducible experimental model for acute ulcerative colitis. Eur Surg Res 1992;24:211–25
   PubMed Web of Science ®Google Scholar
• Nosalova V, Zeman M, Cerna S, et al. Protective effect of melatonin in acetic acid induced colitis in rats. J Pineal Res 2007;42:364–70
   PubMed Web of Science ®Google Scholar
• Winterbourn C-C. Oxidative reactions of hemoglobin. Meth Enzymol 1990;186:265–72
   PubMed Web of Science ®Google Scholar
• Shao Y, Molnar L-F, Jung Y, et al. Advances in methods and algorithms in a modern quantum chemistry program package. Phys Chem Chem Phys 2006;8:3172–91
   PubMed Web of Science ®Google Scholar
• Krieger E, Koraimann G, Vriend G. Increasing the precision of comparative models with YASARA NOVA – a self-parameterizing force field. Proteins [Online] 2002;47:393–402
   PubMed Web of Science ®Google Scholar
• Lee Y-S, Kim S-H, Jung S-H, et al. Aldose reductase inhibitory compounds from Glycyrrhiza uralensis. Biol Pharm Bull 2010;33:917–21
   PubMed Web of Science ®Google Scholar
• Jung H-A, Jung Y-J, Yoon N-Y, et al. Inhibitory effects of Nelumbo nucifera leaves on rat lens aldose reductase, advanced glycation endproducts formation, and oxidative stress. Food Chem Toxicol 2008;46:3818–26
   PubMed Web of Science ®Google Scholar
• Jung H-A, Yoon N-Y, Kang S-S, et al. Inhibitory activities of prenylated flavonoids from Sophora flavescens against aldose reductase and generation of advanced glycation endproducts. J Pharm Pharmacol 2008;60:1227–36
   PubMed Web of Science ®Google Scholar
• Wirasathien L, Pengsuparp T, Suttisri R, et al. Inhibitors of aldose reductase and advanced glycation end-products formation from the leaves of Stelechocarpus cauliflorus R.E. Fr. Phytomedicine 2007;14:546–50
   PubMed Web of Science ®Google Scholar
• Matsuda H, Morikawa T, Toguchida I, Yoshikawa M. Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull (Tokyo) 2002;50:788–95
   PubMed Web of Science ®Google Scholar
• DeRuiter J, Borne R-F, Mayfield C-A. N- and 2-substituted N-(phenylsulfonyl)glycines as inhibitors of rat lens aldose reductase. J Med Chem 1989;32:145–51
   PubMed Web of Science ®Google Scholar
• DeRuiter J, Mayfield C-A. Inhibitory activity and mechanism of inhibition of the N-[[(4-benzoylamino)phenyl]sulfonyl]amino acid aldose reductase inhibitors. Biochem Pharmacol 1990;40:2219–26
   PubMed Web of Science ®Google Scholar
• Haraguchi H, Hayashi R, Ishizu T, Yagi A. A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro. Planta Med 2003;69:853–5
   PubMed Web of Science ®Google Scholar
• Terashima H, Hama K, Yamamoto R, et al. Effects of a new aldose reductase inhibitor on various tissues in vitro. J Pharmacol Exp Ther 1984;229:226–30
   PubMed Web of Science ®Google Scholar
• Camuesco D, Comalada M, Rodríguez-Cabezas M-E, et al. The intestinal anti-inflammatory effect of quercitrin is associated with an inhibition in iNOS expression. Br J Pharmacol 2004;143:908–18
   PubMed Web of Science ®Google Scholar
• Kwon H-K, Murakami A, Tanaka T, Ohigashi H. Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: attenuation of pro-inflammatory gene expression. Biochem Pharmacol 2005;69:395–406
   PubMed Web of Science ®Google Scholar
• Comalada M, Camuesco D, Sierra S, et al. In vivo quercitrin anti-inflammatory effect involves release of quercetin, which inhibits inflammation through down-regulation of the NF-kappaB pathway. Eur J Immunol 2005;35:584–92
   PubMed Web of Science ®Google Scholar
• Guazelli C-F, Fattori V, Colombo B-B, et al. Quercetin-loaded microcapsules ameliorate experimental colitis in mice by anti-inflammatory and antioxidant mechanisms. J Nat Prod 2013;76:200–8
   PubMed Web of Science ®Google Scholar
• Crespy V, Morand C, Besson C, et al. Quercetin, but not its glycosides, is absorbed from the rat stomach. J Agric Food Chem 2002;50:618–21
   PubMed Web of Science ®Google Scholar
• Manach C, Scalbert A, Morand C, et al. Polyphenols: food sources and bioavailability. Am J Clin Nutr 2004;79:727–47
   PubMed Web of Science ®Google Scholar