The identification of novel, high affinity AQP9 inhibitors in an intracellular binding site

References

• Amiry-Moghaddam M, Otsuka T, Hurn PD, Traystman RJ, Haug FM, Froehner SC, 2003. An alpha-syntrophin-dependent pool of AQP4 in astroglial end-feet confers bidirectional water flow between blood and brain. Proc Natl Acad Sci USA 100:2106–2111.
   PubMed Web of Science ®Google Scholar
• Amiry-Moghaddam M, Xue R, Haug FM, Neely JD, Bhardwaj A, Agre P, 2004. Alpha-syntrophin deletion removes the perivascular but not endothelial pool of aquaporin-4 at the blood-brain barrier and delays the development of brain edema in an experimental model of acute hyponatremia. FASEB J 18:542–544.
   PubMedGoogle Scholar
• Arnold K, Bordoli L, Kopp J, Schwede T. 2006. The SWISS-MODEL workspace: A web-based environment for protein structure homology modelling. Bioinformatics 22:195–201.
   PubMed Web of Science ®Google Scholar
• Beitz E, Wu B, Holm LM, Schultz JE, Zeuthen T. 2006. Point mutations in the aromatic/arginine region in aquaporin 1 allow passage of urea, glycerol, ammonia, and protons. Proc Natl Acad Sci USA 103:269–274.
   PubMed Web of Science ®Google Scholar
• Berendsen HJC, Grigera JR, Straatsma TP. 1987. The missing term in effective pair potentials. J Phys Chem 91:6269–6271.
   Web of Science ®Google Scholar
• Berendsen HJC, Postma JPM, Van Gunsteren WF, Dinola A, Haak JR. 1984. Molecular dynamics with coupling to an external bath. J Chem Phys 81:3684.
   Web of Science ®Google Scholar
• Berger O, Edholm O, Jähnig F. 1997. Molecular dynamics simulations of a fluid bilayer of dipalmitoylphosphatidylcholine at full hydration, constant pressure, and constant temperature. Biophys J 72:2002–2013.
   PubMed Web of Science ®Google Scholar
• Brooks HL, Regan JW, Yool AJ. 2000. Inhibition of aquaporin-1 water permeability by tetraethylammonium: Involvement of the loop E pore region. Mol Pharmacol 57:1021–1026.
   PubMed Web of Science ®Google Scholar
• Bussi G, Donadio D, Parrinello M. 2007. Canonical sampling through velocity rescaling. J Chem Phys 126:014101.
   PubMed Web of Science ®Google Scholar
• Dang LX. 1992. Development of nonadditive intermolecular potentials using molecular dynamics: Solvation of Li+ and F- ions in polarizable water. J Chem Phys 96:6970–6977.
   Web of Science ®Google Scholar
• Danielson JA, Johanson U. 2010. Phylogeny of major intrinsic proteins. Adv Exp Med Biol 679:19–31.
   PubMedGoogle Scholar
• Darden T, York D, Pedersen L. 1993. Particle mesh Ewald: An N*log (N) method for Ewald sums in large systems. J Chem Phys 98:10089.
   Web of Science ®Google Scholar
• De Groot BL, Grubmuller H. 2001. Water permeation across biological membranes: Mechanism and dynamics of aquaporin-1 and GlpF. Science 294:2353–2357.
   PubMed Web of Science ®Google Scholar
• Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG. 1995. A smooth particle mesh Ewald method. J Chem Phys 103:8577–8593.
   Web of Science ®Google Scholar
• Fenton RA, Moeller HB, Nielsen S, De Groot BL, Rutzler M. 2010. A plate reader-based method for cell water permeability measurement. Am J Physiol Renal Physiol 298:F224–F230.
   PubMed Web of Science ®Google Scholar
• Fu D, Libson A, Miercke LJ, Weitzman C, Nollert P, Krucinski J, 2000. Structure of a glycerol-conducting channel and the basis for its selectivity. Science 290:481–486.
   PubMed Web of Science ®Google Scholar
• Gonen T, Sliz P, Kistler J, Cheng Y, Walz T. 2004. Aquaporin-0 membrane junctions reveal the structure of a closed water pore. Nature 429:193–197.
   PubMed Web of Science ®Google Scholar
• Gorin MB, Yancey SB, Cline J, Revel JP, Horwitz J. 1984. The major intrinsic protein (MIP) of the bovine lens fiber membrane: Characterization and structure based on cDNA cloning. Cell 39:49–59.
   PubMed Web of Science ®Google Scholar
• Guerrero FD, Jones JT, Mullet JE. 1990. Turgor-responsive gene transcription and RNA levels increase rapidly when pea shoots are wilted. Sequence and expression of three inducible genes. Plant Mol Biol 15:11–26.
   PubMed Web of Science ®Google Scholar
• Hara-Chikuma M, Sugiyama Y, Kabashima K, Sohara E, Uchida S, Sasaki S, 2012. Involvement of aquaporin-7 in the cutaneous primary immune response through modulation of antigen uptake and migration in dendritic cells. FASEB J 26:211–218.
   PubMedGoogle Scholar
• Hess B, Bekker H, Berendsen HJC, Fraaije JGEM. 1997. LINCS: A linear constraint solver for molecular simulations. J Comput Chem 18:1463–1472.
   Web of Science ®Google Scholar
• Hess B, Kutzner C, Van Der Spoel D, Lindahl E. 2008. GROMACS 4: Algorithms for highly efficient, load-balanced, and scalable molecular simulation. J Chem Theory Computat 4:435–447.
   PubMed Web of Science ®Google Scholar
• Horsefield R, Norden K, Fellert M, Backmark A, Tornroth-Horsefield S, Terwisscha Van Scheltinga AC, 2008. High-resolution x-ray structure of human aquaporin 5. Proc Natl Acad Sci USA 105:13327–13332.
   PubMed Web of Science ®Google Scholar
• Huber VJ. 2009. Support for small molecule inhibition of aquaporin 4. Bioorg Med Chem 17:425–426.
   PubMedGoogle Scholar
• Huber VJ, Tsujita M, Kwee IL, Nakada T. 2009a. Inhibition of aquaporin 4 by antiepileptic drugs. Bioorg Med Chem 17:418–424.
   PubMed Web of Science ®Google Scholar
• Huber VJ, Tsujita M, Nakada T. 2012. Aquaporins in drug discovery and pharmacotherapy. Mol Aspects Med 33:691–703.
   PubMed Web of Science ®Google Scholar
• Huber VJ, Tsujita M, Yamazaki M, Sakimura K, Nakada T. 2007. Identification of arylsulfonamides as Aquaporin 4 inhibitors. Bioorg Med Chem Lett 17:1270–1273.
   PubMed Web of Science ®Google Scholar
• Ishibashi K, Hara S, Kondo S. 2009. Aquaporin water channels in mammals. Clin Exp Nephrol 13:107–117.
   PubMed Web of Science ®Google Scholar
• Jelen S, Wacker S, Aponte-Santamaria C, Skott M, Rojek A, Johanson U, 2011. Aquaporin-9 protein is the primary route of hepatocyte glycerol uptake for glycerol gluconeogenesis in mice. J Biol Chem 286:44319–44325.
   PubMed Web of Science ®Google Scholar
• Johnson KD, Hofte H, Chrispeels MJ. 1990. An intrinsic tonoplast protein of protein storage vacuoles in seeds is structurally related to a bacterial solute transporter (GIpF). Plant Cell 2:525–532.
   PubMedGoogle Scholar
• Klokkers J, Langehanenberg P, Kemper B, Kosmeier S, Von Bally G, Riethmuller C, 2009. Atrial natriuretic peptide and nitric oxide signaling antagonizes vasopressin-mediated water permeability in inner medullary collecting duct cells. Am J Physiol Renal Physiol 297:F693–F703.
   Google Scholar
• Larkin MA, Blackshields G, Brown NP, Chenna R, Mcgettigan PA, Mcwilliam H, 2007. Clustal W and Clustal X version 2.0. Bioinformatics 23:2947–2948.
   PubMed Web of Science ®Google Scholar
• Lindorff-Larsen K, Piana S, Palmo K, Maragakis P, Klepeis JL, Dror RO, 2010. Improved side-chain torsion potentials for the Amber ff99SB protein force field. Proteins 78:1950–1958.
   PubMed Web of Science ®Google Scholar
• Ma B, Xiang Y, Mu SM, Li T, Yu HM, Li XJ. 2004. Effects of acetazolamide and anordiol on osmotic water permeability in AQP1-cRNA injected Xenopus oocyte. Acta Pharmacol Sin 25:90–97.
   PubMed Web of Science ®Google Scholar
• Manley GT, Fujimura M, Ma T, Noshita N, Filiz F, Bollen AW, 2000. Aquaporin-4 deletion in mice reduces brain edema after acute water intoxication and ischemic stroke. Nat Med 6:159–163.
   PubMed Web of Science ®Google Scholar
• Marignier R, Giraudon P, Vukusic S, Confavreux C, Honnorat J. 2010. Anti-aquaporin-4 antibodies in Devic's neuromyelitis optica: Therapeutic implications. Ther Adv Neurol Disord 3:311–321.
   PubMedGoogle Scholar
• Migliati E, Meurice N, Dubois P, Fang JS, Somasekharan S, Beckett E, 2009. Inhibition of aquaporin-1 and aquaporin-4 water permeability by a derivative of the loop diuretic bumetanide acting at an internal pore-occluding binding site. Mol Pharmacol 76:105–112.
   PubMed Web of Science ®Google Scholar
• Miyamoto S, Kollman PA. 1992. Settle: An analytical version of the SHAKE and RATTLE algorithm for rigid water models. J Comput Chem 13:952–962.
   Web of Science ®Google Scholar
• Mola MG, Nicchia GP, Svelto M, Spray DC, Frigeri A. 2009. Automated cell-based assay for screening of aquaporin inhibitors. Anal Chem 81:8219–8229.
   PubMed Web of Science ®Google Scholar
• Muramatsu S, Mizuno T. 1989. Nucleotide sequence of the region encompassing the glpKF operon and its upstream region containing a bent DNA sequence of Escherichia coli. Nucleic Acids Res 17:4378.
   PubMedGoogle Scholar
• Papadopoulos MC, Manley GT, Krishna S, Verkman AS. 2004. Aquaporin-4 facilitates reabsorption of excess fluid in vasogenic brain edema. FASEB J 18:1291–1293.
   PubMed Web of Science ®Google Scholar
• Parrinello M, Rahman A. 1980. Crystal structure and pair potentials: A molecular-dynamics study. Phys Rev Lett 45:1196–1199.
   Web of Science ®Google Scholar
• Parrinello M, Rahman A. 1981. Polymorphic transitions in single crystals: A new molecular dynamics method J Appl Phys. 52:7182–7191.
   Google Scholar
• Preston GM, Agre P. 1991. Isolation of the cDNA for erythrocyte integral membrane protein of 28 kilodaltons: Member of an ancient channel family. Proc Natl Acad Sci USA 88:11110–11114.
   PubMed Web of Science ®Google Scholar
• Preston GM, Carroll TP, Guggino WB, Agre P. 1992. Appearance of water channels in Xenopus oocytes expressing red cell CHIP28 protein. Science 256:385–387.
   PubMed Web of Science ®Google Scholar
• Rao Y, Jan LY, Jan YN. 1990. Similarity of the product of the Drosophila neurogenic gene big brain to transmembrane channel proteins. Nature 345:163–167.
   PubMed Web of Science ®Google Scholar
• Rarey M, Kramer B, Lengauer T, Klebe G. 1996. A fast flexible docking method using an incremental construction algorithm. J Mol Biol 261:470–489.
   PubMed Web of Science ®Google Scholar
• Reddy ChS, Vijayasarathy K, Srinivas E, Sastry GM, Sastry GN. 2006. Homology modeling of membrane proteins: A critical assessment. Comput Biol Chem 30:120–126.
   PubMed Web of Science ®Google Scholar
• Rojek A, Praetorius J, Frokiaer J, Nielsen S, Fenton RA. 2008. A current view of the mammalian aquaglyceroporins. Annu Rev Physiol 70:301–327.
   PubMed Web of Science ®Google Scholar
• Rojek AM, Skowronski MT, Fuchtbauer EM, Fuchtbauer AC, Fenton RA, Agre P, 2007. Defective glycerol metabolism in aquaporin 9 (AQP9) knockout mice. Proc Natl Acad Sci USA 104:3609–3614.
   PubMed Web of Science ®Google Scholar
• Saadoun S, Papadopoulos MC, Hara-Chikuma M, Verkman AS. 2005. Impairment of angiogenesis and cell migration by targeted aquaporin-1 gene disruption. Nature 434:786–792.
   PubMed Web of Science ®Google Scholar
• Sadowski J, Gasteiger J, Klebe G. 1994. Comparison of automatic three-dimensional model builders using 639 X-ray structures. J Chem Inf Comput Sci 34:1000–1008.
   Google Scholar
• Sandal NN, Marcker KA. 1988. Soybean nodulin 26 is homologous to the major intrinsic protein of the bovine lens fiber membrane. Nucleic Acids Res 16:9347.
   PubMedGoogle Scholar
• Seeliger D, De Groot BL. 2010. Ligand docking and binding site analysis with PyMOL and Autodock/Vina. J Comput Aided Mol Des 24:417–422.
   PubMed Web of Science ®Google Scholar
• Sogaard R, Zeuthen T. 2008. Test of blockers of AQP1 water permeability by a high-resolution method: No effects of tetraethylammonium ions or acetazolamide. Pflugers Arch 456:285–292.
   PubMedGoogle Scholar
• Trott O, Olson AJ. 2010. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:455–461.
   PubMed Web of Science ®Google Scholar
• Vajda Z, Pedersen M, Fuchtbauer EM, Wertz K, Stodkilde-Jorgensen H, Sulyok E, 2002. Delayed onset of brain edema and mislocalization of aquaporin-4 in dystrophin-null transgenic mice. Proc Natl Acad Sci USA 99:13131–13136.
   PubMedGoogle Scholar
• Walz T, Fujiyoshi Y, Engel A. 2009. The AQP structure and functional implications. Handb Exp Pharmacol 31–56.
   PubMedGoogle Scholar
• Van Der Spoel D, Lindahl E, Hess B, Groenhof G, Mark AE, Berendsen HJC. 2005. GROMACS: Fast, flexible, and free. J Comput Chem 26:1701.
   PubMed Web of Science ®Google Scholar
• Wang J, Wang W, Kollman PA, Case DA. 2006. Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model 25:247–260.
   PubMed Web of Science ®Google Scholar
• Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA. 2004. Development and testing of a general amber force field. J Comput Chem 25:1157–1174.
   PubMed Web of Science ®Google Scholar
• Yamamoto YT, Cheng CL, Conkling MA. 1990. Root-specific genes from tobacco and Arabidopsis homologous to an evolutionarily conserved gene family of membrane channel proteins. Nucleic Acids Res 18:7449.
   PubMedGoogle Scholar
• Yang B, Kim JK, Verkman AS. 2006. Comparative efficacy of HgCl2 with candidate aquaporin-1 inhibitors DMSO, gold, TEA+ and acetazolamide. FEBS Lett 580:6679–6684.
   PubMedGoogle Scholar
• Yang B, Zhang H, Verkman AS. 2008. Lack of aquaporin-4 water transport inhibition by antiepileptics and arylsulfonamides. Bioorg Med Chem 16:7489–7493.
   PubMed Web of Science ®Google Scholar
• Zhu F, Tajkhorshid E, Schulten K. 2004. Collective diffusion model for water permeation through microscopic channels. Phys Rev Lett 93:224501.
   PubMed Web of Science ®Google Scholar