Structure-activity relationship of cyclic ADP-ribose, an update

doi:10.5246/jcps.2013.02.017

摘要/Abstract

摘要：

Cyclic ADP-ribose (cADPR) is a universal Ca²⁺ mobilizing second messenger in many different cell types and organisms. cADPR activates Ca²⁺ release from endo/sarcoplasmic reticulum via ryanodine receptors. In addition, Ca²⁺ entry secondary to Ca²⁺ depletion is at least one of the mechanisms in which cADPR triggers Ca²⁺ inflow, too. Analogues of cADPR have been prepared by chemical and chemo-enzymatic routes. Most of the analogues were analyzed for biological activity in intact or permeabilized Jurkat T cells (a human T-lymphoma cell line). As a systematic approach, analogues were grouped according to alterations in the base, the northern ribose, the southern ribose, the pyrophosphate backbone, or in complex modifications, comprising more than one part of the molecule. Biological activity of the analogues is reviewed, with special emphasis on Jurkat T cells.

关键词: Cyclic ADP-ribose, Calcium signaling, Cyclic ADP-ribose analogue, Ryanodine receptor, TRPM2, Cellular signal transduction

Abstract:

Key words: Cyclic ADP-ribose, Calcium signaling, Cyclic ADP-ribose analogue, Ryanodine receptor, TRPM2, Cellular signal transduction

中图分类号:

R916

Supporting: Foundation items: Deutsche Forschungsgemeinschaft, the Gemeinnützige Hertie-Stiftung, the Wellcome Trust, and the Deutsche Akademische Austauschdienst.
Corresponding author. Tel.: 0049-40-7410-52828; Fax: 0049-40-7410-56818;

Andreas H. Guse^*. Structure-activity relationship of cyclic ADP-ribose, an update[J]. , DOI: 10.5246/jcps.2013.02.017.

参考文献

[1] Zalk, R.; Lehnart, S.E.; Marks, A.R. Annu. Rev. Biochem. 2007, 76, 367-385.
[2] Patterson, R.L.; Boehning, D.; Snyder, S.H. Annu. Rev. Biochem. 2004, 73, 437-465.
[3] Plattner, H. Bioessays. 2002, 24, 649-658.
[4] Yoo, S.H. Cell Calcium. 2011, 50, 175-183.
[5] Batistič, O.; Kudla, J. Biochim. Biophys. Acta. 2012, 1820, 1283-1293.
[6] Ranty, B.; Cotelle, V.; Galaud, J.P.; Mazars, C. Adv. Exp. Med. Biol. 2012, 740, 1123-1143.
[7] Guse, A.H. Curr. Med. Chem. 2004, 11, 847-855.
[8] Sumoza-Toledo, A.; Penner, R. J. Physiol. 2011, 589, 1515-1525.
[9] Guse, A.H.; Lee, H.C. Sci. Signal. 2008, Nov 4, 1: re10.
[10] Clapper, D.L.; Walseth, T.F.; Dargie, P.J.; Lee, H.C. J. Biol. Chem. 1987, 262, 9561-9568.
[11] Lee, H.C.; Walseth, T.F.; Bratt, G.T.; Hayes, R.N.; Clapper, D.L. J. Biol. Chem. 1989, 264, 1608-1615.
[12] Lee, H.C. J. Biol. Chem. 2012, 287, 31633-31640.
[13] Venturi, E.; Pitt, S.; Galfré, E.; Sitsapesan, R. Cardiovasc. Ther. 2012, 30, 109-116.
[14] Fliegert, R.; Gasser, A.; Guse, A.H. Biochem. Soc. Trans. 2007, 35, 109-114.
[15] Guse, A.H. Curr. Mol. Med. 2004, 4, 239-248.
[16] Potter, B.V.; Walseth, T.F. Curr. Mol. Med. 2004, 4, 303-311.
[17] Higashida, H.; Egorova, A.; Higashida, C.; Zhong, Z.G.; Yokoyama, S.; Noda, M.; Zhang, J.S. J. Biol. Chem. 1999, 274, 33348-33354.
[18] Guse, A.H.; da Silva, C.P.; Berg, I.; Skapenko, A.L.; Weber, K.; Heyer, P.; Hohenegger, M.; Ashamu, G.A.; Schulze-Koops, H.; Potter, B.V.; Mayr, G.W. Nature. 1999, 398, 70-73.
[19] Hellmich, M.R.; Strumwasser, F. Cell Regul. 1991, 2, 193-202.
[20] Howard, M.; Grimaldi, J.C.; Bazan, J.F.; Lund, F.E.; Santos-Argumedo, L.; Parkhouse, R.M.; Walseth, T.F.; Lee, H.C. Science. 1993, 262, 1056-1059.
[21] Bruzzone, S.; Franco, L.; Guida, L.; Zocchi, E.; Contini, P.; Bisso, A.; Usai, C.; De Flora, A. J. Biol. Chem. 2001, 276, 48300-48308.
[22] Guida, L.; Bruzzone, S.; Sturla, L.; Franco, L.; Zocchi, E.; De Flora, A. J. Biol. Chem. 2002, 277, 47097-47105.
[23] Zhao, Y.J.; Lam, C.M.; Lee, H.C. Sci. Signal. 2012, 5: ra67.
[24] Partida-Sánchez, S.; Cockayne, D.A.; Monard, S.; Jacobson, E.L.; Oppenheimer, N.; Garvy, B.; Kusser, K.; Goodrich, S.; Howard, M.; Harmsen, A.; Randall, T.D.; Lund, F.E. Nat. Med. 2001, 7, 1209-1216.

[25] Ceni, C.; Muller-Steffner, H.; Lund, F.; Pochon, N.; Schweitzer, A.; De Waard, M.; Schuber, F.; Villaz, M.; Moutin, M.J. J. Biol. Chem. 2003, 278, 40670-40678.
[26] Kirchberger, T.; Wagner, G.; Xu, J.; Cordiglieri, C.; Wang, P.; Gasser, A.; Fliegert, R.; Bruhn, S.; Flügel, A.; Lund, F.E.; Zhang, L.H.; Potter, B.V.; Guse, A.H. Br. J. Pharmacol. 2006, 149, 337-344.
[27] Noguchi, N.; Takasawa, S.; Nata, K.; Tohgo, A.; Kato, I.; Ikehata, F.; Yonekura, H.; Okamoto, H. J. Biol. Chem. 1997, 272, 3133-3136.
[28] Lee, H.C.; Aarhus, R.; Graeff, R.; Gurnack, M.E.; Walseth, T.F. Nature. 1994, 370, 307-309.
[29] Schwarzmann, N.; Kunerth, S.; Weber, K.; Mayr, G.W.; Guse, A.H. J. Biol. Chem. 2002, 277, 50636-50642.
[30] Guse, A.H.; Berg, I.; da Silva, C.P.; Potter, B.V.; Mayr, G.W. J. Biol. Chem. 1997, 272, 8546-8550.
[31] Kiselyov, K.; Shin, D.M.; Shcheynikov, N.; Kurosaki, T.; Muallem, S. Biochem. J. 2001, 360, 17-22.
[32] Sieck, G.C.; White, T.A.; Thompson, M.A.; Pabelick, C.M.; Wylam, M.E.; Prakash, Y.S. Am. J. Physiol. Lung Cell Mol. Physiol. 2008, 294, L378-385.
[33] Yu, P.L.; Zhang, Z.H.; Hao, B.X.; Zhao, Y.J.; Zhang, L.H.; Lee, H.C.; Zhang, L.; Yue, J. J. Biol. Chem. 2012, 287, 24774-24783.
[34] Shuto, S.; Fukuoka, M.; Manikowsky, A.; Ueno, Y.; Nakano, T.; Kuroda, R.; Kuroda, H.; Matsuda, A. J. Am. Chem. Soc. 2001, 123, 8750-8759.
[35] Guse, A.H.; Roth, E.; Emmrich, F. Biochem. J. 1993, 291, 447-451.
[36] Gu, X.; Yang, Z.; Zhang, L.; Kunerth, S.; Fliegert, R.; Weber, K.; Guse, A.H.; Zhang, L. J. Biol. Chem. 2004, 47, 5674-5682.
[37] Walseth, T.F.; Lee, H.C. Biochim. Biophys. Acta. 1993, 1178, 235-242.
[38] Guse, A.H.; da Silva, C.P.; Emmrich, F.; Ashamu, G.A.; Potter, B.V.; Mayr, G.W. J. Immunol. 1995, 155, 3353-3359.
[39] Zhang, B.; Wagner, G.K.; Weber, K.; Garnham., C.; Morgan, A.J.; Galione, A.; Guse, A.H.; Potter, B.V. J. Biol. Chem. 2008, 51, 1623-1636.
[40] Wagner, G.K.; Guse, A.H.; Potter, B.V. J. Org. Chem. 2005, 70, 4810-4819.
[41] Moreau, C.; Wagner, G.K.; Weber, K.; Guse, A.H.; Potter, B.V. J. Med. Chem. 2006, 49, 5162-5176.
[42] Kirchberger, T.; Moreau, C.; Wagner, G.K.; Fliegert, R.; Siebrands, C.C.; Nebel, M.; Schmid, F.; Harneit, A.; Odoardi, F.; Flügel, A.; Potter, B.V.; Guse, A.H. Biochem. J. 2009, 422, 139-149.
[43] Moreau, C.; Kirchberger, T.; Zhang, B.; Thomas, M.P.; Weber, K.; Guse, A.H.; Potter, B.V. J. Med. Chem. 2012, 55, 1478-1489.
[44] Wong, L.; Aarhus, R.; Lee, H.C.; Walseth, T.F. Biochim. Biophys. Acta. 1999, 1472, 555-564.
[45] Guse, A.H.; Cakir-Kiefer, C.; Fukuoka, M.; Shuto, S.; Weber, K.; Bailey, V.C.; Matsuda, A.; Mayr, G.W.; Oppenheimer, N.; Schuber, F.; Potter, B.V. Biochemistry. 2002, 41, 6744-6751.
[46] Kudoh, T.; Fukuoka, M.; Ichikawa, S.; Murayama, T.; Ogawa, Y.; Hashii, M.; Higashida, H.; Kunerth, S.; Weber, K.; Guse, A.H.; Potter, B.V.; Matsuda, A.; Shuto, S. J. Am. Chem. Soc. 2005, 127, 8846-8855.
[47] Xu, J.; Yang, Z.; Dammermann, W.; Zhang, L.; Guse, A.H.; Zhang, L.H. J. Med. Chem. 2006, 49, 5501-5512.
[48] Vu, C.Q.; Lu, P.J.; Chen, C.S.; Jacobson, M.K. J. Biol. Chem. 1996, 271, 4747-4754.
[49] Guse, A.H.; da Silva, C.P.; Weber, K.; Armah, C.N.; Ashamu, G.A.; Schulze, C.; Potter, B.V.; Mayr, G.W.; Hilz, H. Eur. J. Biochem. 1997, 245, 411-417.
[50] Xu, L.; Walseth, T.F.; Slama, J.T. J. Med. Chem. 2005, 48, 4177-4181.
[51] Zhang, F.J.; Gu, Q.M.; Sih, C.J. Bioorg. Med. Chem. 1999, 7, 653-664.
[52] Kunerth, S.; Langhorst, M.F.; Schwarzmann, N.; Gu, X.; Huang, L.; Yang, Z.; Zhang, L.; Mills, S.J.; Zhang, L.H.; Potter, B.V.; Guse, A.H. J. Cell Sci. 2004, 117, 2141-2149.
[53] Dong, M.; Kirchberger, T.; Huang, X.; Yang, Z.J.; Zhang, L.R.; Guse, A.H.; Zhang, L.H. Org. Biomol. Chem. 2010, 8, 4705-4715.
[54] Guse, A.H.; Gu, X.; Zhang, L.; Weber, K.; Krämer, E.; Yang, Z.; Jin, H.; Li, Q.; Carrier, L.; Zhang, L. J. Biol. Chem. 2005, 280, 15952-15959.
[55] Kudoh, T.; Murayama, T.; Hashii, M.; Higashida, H.; Sakurai, T.; Maechling, C.; Spiess, B.; Weber, K.; Guse, A.H.; Potter, B.V.; Arisawa, M.; Matsuda, A.; Shuto, S. Tetrahedron. 2008, 64, 9754-9765.
[56] Qi, N.; Jung, K.; Wang, M.; Na, L.X.; Yang, Z.J.; Zhang, L.R.; Guse, A.H.; Zhang, L.H. Chem. Commun (Camb). 2011, 47, 9462-9464.
[57] Li, L.; Siebrands, C.C.; Yang, Z.; Zhang, L.; Guse, A.H.; Zhang, L. Org. Biomol. Chem. 2010, 8, 1843-1848.