Identification of a chemical probe for NAADP by virtual screening

Lee, H.C. Nicotinic acid adenine dinucleotide phosphate (NAADP)-mediated calcium signaling. J. Biol. Chem. 280, 33693–33696 (2005).

Galione, A., Parrington, J. & Dowden, J. The NAADP receptor: commentary on Billington et al. Br. J. Pharmacol. 142, 1203–1207 (2004).

Lee, H.C. & Aarhus, R. A derivative of NADP mobilizes calcium stores insensitive to inositol trisphosphate and cyclic ADP-ribose. J. Biol. Chem. 270, 2152–2157 (1995).

Giniatullin, R., Nistri, A. & Yakel, J.L. Desensitization of nicotinic ACh receptors: shaping cholinergic signaling. Trends Pharmacol. Sci. 28, 371–378 (2005).

Cancela, J.M., Churchill, G.C. & Galione, A. Coordination of agonist-induced Ca2+-signalling patterns by NAADP in pancreatic acinar cells. Nature 398, 74–76 (1999).

Masgrau, R., Churchill, G.C., Morgan, A.J., Ashcroft, S.J. & Galione, A. NAADP: a new second messenger for glucose-induced Ca2+ responses in clonal pancreatic beta cells. Curr. Biol. 13, 247–251 (2003).

Patel, S. NAADP-induced Ca2+ release–a new signalling pathway. Biol. Cell 96, 19–28 (2004).

Churchill, G.C. et al. NAADP mobilizes Ca2+ from reserve granules, lysosome-related organelles, in sea urchin eggs. Cell 111, 703–708 (2002).

Yamasaki, M. et al. Organelle selection determines agonist-specific Ca2+ signals in pancreatic acinar and beta cells. J. Biol. Chem. 279, 7234–7240 (2004).

Gerasimenko, J.V., Sherwood, M., Tepikin, A.V., Petersen, O.H. & Gerasimenko, O.V. NAADP, cADPR and IP3 all release Ca2+ from the endoplasmic reticulum and an acidic store in the secretory granule area. J. Cell Sci. 119, 226–238 (2006).

Galione, A. & Petersen, O.H. The NAADP receptor: new receptors or new regulation? Mol. Interv. 5, 73–79 (2005).

Mitchell, K.J., Lai, F.A. & Rutter, G.A. Ryanodine receptor type I and nicotinic acid adenine dinucleotide phosphate receptors mediate Ca2+ release from insulin-containing vesicles in living pancreatic beta-cells (MIN6). J. Biol. Chem. 278, 11057–11064 (2003).

Genazzani, A.A., Empson, R.M. & Galione, A. Unique inactivation properties of NAADP-sensitive Ca2+ release. J. Biol. Chem. 271, 11599–11602 (1996).

Morgan, A.J. et al. Methods in cyclic ADP-ribose and NAADP research. in Methods in Calcium Signalling (ed. Putney, J.W.J.) 265–333 (CRC Press, Boca Raton, Florida, USA, 2006).

Brailoiu, E. et al. Nicotinic acid adenine dinucleotide phosphate potentiates neurite outgrowth. J. Biol. Chem. 280, 5646–5650 (2005).

Billington, R.A. et al. Production and characterization of reduced NAADP (nicotinic acid-adenine dinucleotide phosphate). Biochem. J. 378, 275–280 (2004).

Billington, R.A., Tron, G.C., Reichenbach, S., Sorba, G. & Genazzani, A.A. Role of the nicotinic acid group in NAADP receptor selectivity. Cell Calcium 37, 81–86 (2005).

Lee, H.C. & Aarhus, R. Structural determinants of nicotinic acid adenine dinucleotide phosphate important for its calcium-mobilizing activity. J. Biol. Chem. 272, 20378–20383 (1997).

Lee, H.C. & Aarhus, R. Fluorescent analogs of NAADP with calcium mobilizing activity. Biochim. Biophys. Acta 1425, 263–271 (1998).

Dowden, J. et al. Cell-permeant small-molecule modulators of NAADP-mediated Ca2+ release. Chem. Biol. 13, 659–665 (2006).

Lipinski, C.A., Lombardo, F., Dominy, B.W. & Feeney, P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 23, 3–25 (1997).

Billington, R.A., Bak, J., Martinez-Coscolla, A., Debidda, M. & Genazzani, A.A. Triazine dyes are agonists of the NAADP receptor. Br. J. Pharmacol. 142, 1241–1246 (2004).

Billington, R.A. & Genazzani, A.A. PPADS is a reversible competitive antagonist of the NAADP receptor. Cell Calcium 41, 505–511 (2007).

Jorgensen, W.L. The many roles of computation in drug discovery. Science 303, 1813–1818 (2004).

Oprea, T.I. & Matter, H. Integrating virtual screening in lead discovery. Curr. Opin. Chem. Biol. 8, 349–358 (2004).

Shoichet, B.K. Virtual screening of chemical libraries. Nature 432, 862–865 (2004).

Drews, J. Drug discovery: a historical perspective. Science 287, 1960–1964 (2000).

Klebe, G. Virtual ligand screening: strategies, perspectives and limitations. Drug Discov. Today 11, 580–594 (2006).

Irwin, J.J. & Shoichet, B.K. ZINC–a free database of commercially available compounds for virtual screening. J. Chem. Inf. Model. 45, 177–182 (2005).

Rush, T.S. III, Grant, J.A., Mosyak, L. & Nicholls, A. A shape-based 3-D scaffold hopping method and its application to a bacterial protein-protein interaction. J. Med. Chem. 48, 1489–1495 (2005).

Nicholls, A., MacCuish, N.E. & MacCuish, J.D. Variable selection and model validation of 2D and 3D molecular descriptors. J. Comput. Aided Mol. Des. 18, 451–474 (2004).

Galione, A. & Ruas, M. NAADP receptors. Cell Calcium 38, 273–280 (2005).

Boström, J., Berggren, K., Elebring, T., Greasleya, P.J. & Wilstermanna, M. Scaffold hopping, synthesis and structure–activity relationships of 5,6-diaryl-pyrazine-2-amide derivatives: a novel series of CB1 receptor antagonists. Bioorg. Med. Chem. 15, 4077–4084 (2007).

Hawkins, P.C.D., Skillman, A.G. & Nicholls, A. Comparison of shape-matching and docking as virtual screening tools. J. Med. Chem. 50, 74–82 (2007).

Jenkins, J.L., Glick, M. & Davies, J.W. A 3D similarity method for scaffold hopping from known drugs or natural ligands to new chemotypes. J. Med. Chem. 47, 6144–6159 (2004).

Boström, J., Greenwood, J.R. & Gottfries, J. Assessing the performance of OMEGA with respect to retrieving bioactive conformations. J. Mol. Graph. Model. 21, 449–462 (2003).

Grant, J.A., Gallardo, M.A. & Pickup, B.T. A fast method of molecular shape comaprison: a simple application of a Gaussian description of molecular shape. J. Comput. Chem. 17, 1653–1666 (1996).

Doman, T.N. et al. Molecular docking and high-throughput screening for novel inhibitors of protein tyrosine phosphatase-1B. J. Med. Chem. 45, 2213–2221 (2002).

Aarhus, R. et al. Activation and inactivation of Ca2+ release by NAADP+. J. Biol. Chem. 271, 8513–8516 (1996).

Giepmans, B.N., Adams, S.R., Ellisman, M.H. & Tsien, R.Y. The fluorescent toolbox for assessing protein location and function. Science 312, 217–224 (2006).

Johnson, J.D. & Misler, S. Nicotinic acid-adenine dinucleotide phosphate-sensitive calcium stores initiate insulin signalling in human beta cells. Proc. Natl. Acad. Sci. USA 99, 14566–14571 (2002).

Arredouani, A., Henquin, J.C. & Gilon, P. Contribution of the endoplasmic reticulum to the glucose-induced Ca2+ response in mouse pancreatic islets. Am. J. Physiol. Endocrinol. Metab. 282, E982–E991 (2002).

Tan, D.S. Diversity-orientated synthesis: exploring the intersections between biology and chemistry. Nat. Chem. Biol. 1, 74–84 (2005).

Ashcroft, F.M., Harrison, D.E. & Ashcroft, S.J. Glucose induces closure of single potassium channels in isolated rat pancreatic beta-cells. Nature 312, 446–448 (1984).

Seghers, V., Nakazaki, M., DeMayo, F., Aguilar-Bryan, L. & Bryan, J. Sur1 knockout mice. A model for KATP channel-independent regulation of insulin secretion. J. Biol. Chem. 275, 9270–9277 (2000).

Islam, M.S., Larsson, O. & Berggren, P.O. Cyclic ADP-ribose in beta cells. Science 262, 584–586 (1993).

Takasawa, S., Nata, K., Yonekura, H. & Okamoto, H. Cyclic ADP-ribose in insulin secretion from pancreatic beta cells. Science 259, 370–373 (1993).

Parkesh, R. et al. Cell-permeant NAADP: a novel chemical tool enabling the study of Ca2+ signalling in intact cells. Cell Calcium 43, 531–538 (2007).