Structure-based design, synthesis and biological evaluation of β-glucuronidase inhibitors

Paigen K (1989) Mammalian beta-glucuronidase: genetics, molecular biology, and cell biology. Prog Nucl Acid Res Mol Biol 37:155–205 Islam MR, Grubb JH, Sly WS (1993) C-terminal processing of human beta glucuronidase. The propeptide is required for full expression of catalytic activity, intracellular retention, and proper phosphorylation. J Biol Chem 268:22627–22633 Shipley JM, Grubb JH, Sly WS (1993) The role of glycosylation and phosphorylation in the expression of active human β-glucuronidase. J Biol Chem 268:12193–12198 Kim HW, Mino K, Ishikawa K (2008) Crystallization and preliminary X-ray analysis of endoglucanase from Pyrococcus horikoshii”. Acta Crystallogr Sect F Struct Biol Cryst Commun 64:1169–1171 Jain S, Drendel WB, Chen ZW, Mathews FS, Sly WS, Grubb JH (1996) Structure of human beta-glucuronidase reveals candidate lysosomal targeting and active-site motif. Nat Struct Biol 3:375–381 Sperker B, Mürdter TE, Schick M, Eckhardt K, Bosslet K, Kroemer HK (1997) Interindividual variability in expression and activity of human beta-glucuronidase in liver and kidney: consequences for drug metabolism. J Pharmacol Exp Ther 281:914–920 Bank N, Bailine SH (1965) Urinary beta-glucuronidase activity in patients with urinary-tract infection. N Engl J Med 272:70–75 Roberts AP, Frampton J, Karim SM, Beard RW (1967) Estimation of beta-glucuronidase activity in urinary-tract infection. N Engl J Med 276:1468–1470 Ronald AR, Silverblatt F, Clark H, Cutler RE, Turck M (1971) Failure of urinary beta-glucuronidase activity to localize the site of urinary tract infection. Appl Microbiol 21:990–992 Kallet HA, Lapco L (1967) Urine beta glucuronidase activity in urinary tract disease. J Urol 97:352–356 Gonick HC, Kramer HJ, Schapiro AE (1973) Urinary β-glucuronidase activity in renal disease. Arch Intern Med 132:63–69 Schapiro A, Paul W, Gonick H (1968) Urinary beta-glucuronidase in urologic diseases of the kidneys. J Urol 100:146–157 Plum CM (1967) Beta-glucuronidase activity in serum, cerebrospinal fluid and urine in normal subjects and in neurological and mental patients. Enzymol Biol Clin 8:97–112 Hradec E, Petrík R, Pezlarová J (1965) The activity of beta-glucuronidase in cases of bladder neoplasms. J Urol 94:430–435 Boyland E, Gasson JE, Williams DC (1957) Enzyme activity in relation to cancer; the urinary beta-glucuronidase activity of patients suffering from malignant disease. Br J Cancer 11:120–129 Caygill JC, Pitkeathly DA (1966) BTS/BLF/BALR early career investigator of the year: a study of β-acetylglucosaminase and acid phosphatase in pathological joint fluids. Ann Rheum Dis 25:137–144 Weissmann G, Zurier RB, Spieler PJ, Goldstein IM (1971) Mechanisms of lysosomal enzyme release from leukocytes exposed to immune complexes and other particles. J Exp Med 134:149S–165S Reddy BS (1976) Dietary factors and cancer of the large bowel. Semin Oncol 3:351–359 Goldin BR, Gorbach SL (1976) The relationship between diet and rat fecal bacterial enzymes implicated in colon cancer. J Nat Cancer Inst 57:371–375 Takada H, Hirooka T, Hiramatsu Y, Yamamoto M (1982) Effect of β-glucuronidase inhibitor on azoxymethane-induced colonic carcinogenesis in rats1. Cancer Res 42:331–334 Khan KM, Shujaat S, Rahat S, Hayat S, Choudhary MI (2002) Beta-N-cyanoethyl acyl hydrazide derivatives: a new class of beta-glucuronidase inhibitors. Chem Pharm Bull 50:1443–1446 Khan KM, Rahim F, Wadood A, Taha M, Khan M, Naureen S, Ambreen N, Hussain S, Perveen S, Choudhary MI (2014) Evaluation of bisindole as potent β-glucuronidase inhibitors: synthesis and in silico based studies. Bioorg Med Chem Lett 24:1825–1829 Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Del Rev 23:3–25 MOE (The Molecular Operating Environment), Version 2006.08 (2007) software, Chemical Computing Group Inc., Montreal, Canada.http://www.chemcomp.com SYBYL Molecular Modeling Software Packages, Version 6.9 (2004) Tripos Associates, St Louis, MO http://www.iccs.edu/pcmd/compound_bank.php Abid O, Babar TM, Ali FI, Ahmed S, Wadood A, Rama NH, Uddin R, Ul-Haq Zaheer, Khan A, Choudhary MI (2010) Identification of novel urease inhibitors by high-throughput virtual and in vitro screening. Med Chem Lett 1:145–149 GOLD Version 4.0. (2001) Astex Technology, Cambridge Collins RA, Ng TB, Fong WP, Wan CC, Yeung HW (1997) Inhibition of glycohydrolase enzymes by aqueous extracts of Chinese medicinal herbs in a microplate format. Biochem Mol Biol Int 42:1163–1169 Yamaguchi F, Ariga T, Yoshimura Y, Nakazawa H (2000) Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind. J Agric Food Chem 48:180–185 Mamillapalli R, Haimovitz R, Ohad M, Shinitzky M (1998) Enhancement and inhibition of snake venom phosphodiesterase activity by lysophospholipids. FEBS Lett 436:256–258 López-Gómez J, Costas MJ, Meireles RJ, Fernández A, Romero A, Ávalos M, Cameselle JC (1998) Glycine-enhanced inhibition of rat liver nucleotide pyrophosphatase/phosphodiesterase-I by EDTA: a full account of the reported inhibition by commercial preparations of acidic fibroblast growth factor (FGF-1). FEBS Lett 421:77–79 Razzell WE, Khorana HG (1959) Studies on polynucleotides III. Enzymic degradation. Substrate specificity and properties of snake venom phosphodiesterase. J Biol Chem 234:2105–2113 Nakabayashi T, Matsuoka Y, Ikezawa H, Kimura Y (1994) Alkaline phosphodiesterase I release from eucaryotic plasma membranes by phosphatidylinositol-specific phospholipase C–IV. The release from Cavia porcellus organs. Int J Biochem 26:171–179 Kato K, Yoshida K, Tsukamoto H, Nobunaga M, Masuya T, Sawada T (1960) Synthesis of p-nitro phenyl beta-D-glucopyranosiduronic acid and its utilisation as substrate for assay of beta-glucuronidase activity. Chem Pharm Bull 8:239–242 Islam MR, Tomatsu S, Shah GN, Grubb JH, Jain S, Sly WS (1999) Active site residues of human beta-glucuronidase. Evidence for Glu(540) as the nucleophile and Glu(451) as the acid-base residue. J Biol Chem 274:23451–23455 Kawasaki M, Hayashi T, Arisawa M, Morita N, Berganza L (1988) H.8-hydroxytricetin 7-glucuronide. A β-glucuronidase inhibitor from Scoparia dulcis. Photochemistry 27:3709–3711 Schmeda-Hirschmann G, Loyola JI, Reyes S, Hubert E, Rodriguez M, Rodriguez J, Dutra-Behrens M (1994) β-Glucuronidase inhibition and diuretic activity of Fabiana imbricata R. & P. (Solanaceae). Phytother Res 8:485–487 Hayashi T, Kawasaki M, Okamura K, Tamada Y, Morita N, Tezuka Y, Kikuchi T, Miwa Y, Taga T (1992) Scoparic acid A, A β-glucuronidase inhibitor from Scoparia dulcis. J Nat Prod 55:1748–1755 Cenci di Bello I, Dorling P, Fellows L, Winchester B (1984) Specific inhibition of human β-D-glucuronidase and α-L-iduronidase by a trihydroxy pipecolic acid of plant origin. FEBS Lett 176:61–64 Levy G, Conchi J (1966) β-Glucuronidase and the hydrolysis of glucuronides. In: Dutton GJ (ed) Glucuronic Acid. Academic Press, Free and Combined New York, pp 301–364 Borges F, Roleira F, Milhazes N, Santana L, Uriarte E (2005) Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity. Curr Med Chem 12:887–916 Nicolaides DN, Fylaktakidou KC, Litinas KE, Hadjipavlou-Litina D (1996) Synthesis and biological evaluation of some 4-(isoxazolinyl or 1,2,4-oxadiazolyl) coumarins. J Heterocycl Chem 33:967–971 Burgart YV, Shcherbakov KV, Saloutin VI, Chupakhin ON (2004) 5,6,7,8-Tetrafluoro-4-hydroxycoumarin derivatives in reactions with o-phenylenediamin. Russ Chem Bul 53:1237–1239 Lu J, Li Y, Bai Y, Tian M (2004) Green chemistry approaches to the synthesis of 5-arylidenethiobarbituric acids by a condensation reactions between aromatic aldehydes and thiobarbituric acid: comparison of water, microwave irradiation, and grinding. Heterocycles 63:583–589 Ferreira RS, Bryant C, Ang KKH, McKerrow JH, Shoichet BK, Renslo AR (2009) Divergent modes of enzyme inhibition in a homologous structure–activity series. J Med Chem lett 52:5005–5008