サイクリックADPリボース

関: cyclic ADP-ribose、cyclic ADPR

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/07/12 05:56:16」(JST)

wiki en

Cyclic ADP Ribose, frequently abbreviated as cADPR, is a cyclic adenine nucleotide (like cAMP) with two phosphate groups present on 5' OH of the adenosine (like ADP), further connected to another ribose at the 5' position, which, in turn, closes the cycle by glycosidic bonding to the nitrogen 1 (N¹) of the same adenine base (whose position N⁹ has the glycosidic bond to the other ribose).^[1]^[2] The N¹-glycosidic bond to adenine is what distinguishes cADPR from ADP-ribose (ADPR), the non-cyclic analog. cADPR is produced from nicotinamide adenine dinucleotide (NAD⁺) by ADP-ribosyl cyclases (EC 3.2.2.5) as part of a second messenger system.

Function

cADPR is a cellular messenger for calcium signaling.^[3] It stimulates calcium-induced calcium release at lower cytosolic concentrations of Ca²⁺. Primary target of cADPR is the ER Ca2+ uptake mechanism. Potentiation of Ca2+ release by cADPR is mediated by increased accumulation of Ca2+ in the SR and subsequent luminal Ca2+-dependent activation of ryanodine receptors (RyRs).^[4] Some reports suggest that cADPR binding makes FKBP12.6, which normally binds RyR2, to fall off the RYR2.

Metabolism

cADPR and ADPR are synthesized from NAD⁺ by the bifunctional ectoenzymes of the CD38 family (also includes the GPI-anchored CD157 and the specific, monofunctional ADP ribosyl cyclase of the mollusc Aplysia).^[5]^[6]^[7] The same enzymes are also capable of hydrolyzing cADPR to ADPR. Catalysis proceeds via a covalently bound intermediate. The hydrolysis reaction is inhibited by ATP, and cADPR may accumulate. Synthesis and degradation of cADPR by enzymes of the CD38 family involve, respectively, the formation and the hydrolysis of the N¹-glycosidic bond. In 2009, the first enzyme able to hydrolyze the phosphoanhydride linkage of cADPR, i.e. the one between the two phosphate groups, has been reported.^[8]

References

^ Lee HC, Walseth TF, Bratt GT, Hayes RN, Clapper DL (1989). "Structural determination of a cyclic metabolite of NAD⁺ with intracellular Ca²⁺-mobilizing activity". J. Biol. Chem. 264 (3): 1608–15. PMID 2912976.
^ Lee HC, Aarhus R, Levitt D (1994). "The crystal structure of cyclic ADP-ribose". Nat. Struct. Biol. 1 (3): 143–4. doi:10.1038/nsb0394-143. PMID 7656029.
^ Guse AH (2004). "Regulation of calcium signaling by the second messenger cyclic adenosine diphosphoribose (cADPR)". Curr. Mol. Med. 4 (3): 239–48. doi:10.2174/1566524043360771. PMID 15101682.
^ Lukyanenko V, Györke I, Wiesner TF, Györke S. 2001. Potentiation of Ca(2+) release by cADP-ribose in the heart is mediated by enhanced ER Ca2+ uptake into the sarcoplasmic reticulum. Circ Res. 89(7):614-22. PMID 11577027; 10.1161/hh1901.098066
^ Prasad GS, McRee DE, Stura EA, Levitt DG, Lee HC, Stout CD (1996). "Crystal structure of Aplysia ADP-ribosyl cyclase, a homolog of the bifunctional ectozyme CD38". Nat. Struct. Biol. 3 (11): 957–64. doi:10.1038/nsb1196-957. PMID 8901875.
^ Liu Q, Kriksunov IA, Graeff R, Munshi C, Lee HC, Hao Q (2005). "Crystal structure of the human CD38 extracellular domain". Structure 13 (9): 1331–9. doi:10.1016/j.str.2005.05.012. PMID 16154090.
^ Guse AH (2004). "Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR)". Curr. Med. Chem. 11 (7): 847–55. doi:10.2174/0929867043455602. PMID 15078169.
^ Canales J, Fernández A, Rodrigues JR, Ferreira R, Ribeiro JM, Cabezas A, Costas MJ, Cameselle JC (2009). "Hydrolysis of the phosphoanhydride linkage of cyclic ADP-ribose by the Mn²⁺-dependent ADP-ribose/CDP-alcohol pyrophosphatase". FEBS Lett. 583 (10): 1593–8. doi:10.1016/j.febslet.2009.04.023. PMID 19379742.

External links

The web page of Dr. Hon Cheung Lee, the discoverer of cyclic ADP-ribose.
Cyclic ADP-ribose and NAADP. The first book on these two second messengers.

English Journal

Synthesis of 7-Deaza-cyclic Adenosine-5'-diphosphate-carbocyclic-ribose and Its 7-Bromo Derivative as Intracellular Ca(2+)-Mobilizing Agents.

Takano S, Tsuzuki T, Murayama T1, Sakurai T1, Fukuda H, Arisawa M, Shuto S.
The Journal of organic chemistry.J Org Chem.2015 Jul 2;80(13):6619-27. doi: 10.1021/acs.joc.5b00723. Epub 2015 Jun 23.
Cyclic ADP-carbocyclic-ribose (cADPcR, 3) is a biologically and chemically stable equivalent of cyclic ADP-ribose (cADPR, 1), a Ca(2+)-mobilizing second messenger. We became interested in the biological activity of the 7-deaza analogues of cADPcR, i.e., 7-deaza-cADPcR (7) and its 7-bromo derivative,
PMID 26075947

Omega-3 fatty acids induce Ca(2+) mobilization responses in human colon epithelial cell lines endogenously expressing FFA4.

Kim JM1, Lee KP1, Park SJ1, Kang S1, Huang J1, Lee JM1, Sato K2, Chung HY1, Okajima F2, Im DS1.
Acta pharmacologica Sinica.Acta Pharmacol Sin.2015 Jul;36(7):813-20. doi: 10.1038/aps.2015.29. Epub 2015 May 25.
AIM: Free fatty acid receptor 4 (FFA4; formerly known as GPR120) is the G protein-coupled receptor (GPCR) for omega-3 polyunsaturated fatty acids. FFA4 has been found to express in the small intestines and colons of mice and humans. In this study we investigate the effects of omega-3 polyunsaturated
PMID 26005911

Both RyRs and TPCs are required for NAADP-induced intracellular Ca2+ release.

Gerasimenko JV1, Charlesworth RM1, Sherwood MW2, Ferdek PE1, Mikoshiba K3, Parrington J4, Petersen OH1, Gerasimenko OV5.
Cell calcium.Cell Calcium.2015 Jun 10. pii: S0143-4160(15)00095-0. doi: 10.1016/j.ceca.2015.05.005. [Epub ahead of print]
Intracellular Ca2+ release is mostly mediated by inositol trisphosphate, but intracellular cyclic-ADP-ribose (cADPR) and nicotinic acid adenine dinucleotide phosphate (NAADP) are important messengers in many systems. Whereas cADPR generally activates type 2 ryanodine receptors (RyR2s), the NAADP-act
PMID 26100948

Japanese Journal

Somato-axodendritic release of oxytocin into the brain due to calcium amplification is essential for social memory

Journal of Physiological Sciences 66(4), 275-282, 2016-07-01
NAID 120005682634

Social memory, amnesia, and autism: Brain oxytocin secretion is regulated by NAD + metabolites and single nucleotide polymorphisms of CD38

Neurochemistry International 61(6), 828-838, 2012-11
NAID 120004966608

Oxytocin-induced elevation of ADP-ribosyl cyclase activity, cyclic ADP-riboseor Ca2+ concentrations is involved in autoregulation of oxytocin secretionin the hypothalamus and posterior pituitary in male mice

Neuropharmacology 58(1), 50-55, 2010-01
NAID 120001451026

Related Pictures

★リンクテーブル★

リンク元	「cyclic ADPR」「cyclic ADP-ribose」「サイクリックADPリボース」
拡張検索	「cADPR hydrolase」「cADPRヒドロラーゼ」「cADPR加水分解酵素」

「cyclic ADPR」

Cyclic ADP-ribose
Identifiers
CAS Number	119340-53-3
ChEBI	CHEBI:31445
ChemSpider	21403087
IUPHAR/BPS	2445
Jmol 3D model	Interactive image
MeSH	Cyclic+ADP-Ribose
PubChem	123847
	InChI InChI=1S/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1 Key: BQOHYSXSASDCEA-KEOHHSTQSA-N ; InChI=1/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1 Key: BQOHYSXSASDCEA-KEOHHSTQBN ;
	SMILES O[C@H]5[C@@H](O)[C@H]2O[C@@H]5COP(O)(=O)OP(O)(=O)OC[C@H]4O[C@@H](N3\C=N/c1c(ncn12)C3=N)[C@H](O)[C@@H]4O ;
Properties
Chemical formula	C15H21N5O13P2
Molar mass	541.301
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

サイクリックADPリボース

関: cADPR、cyclic ADP-ribose

「cyclic ADP-ribose」

　　[★]

サイクリックADPリボース

関: cADPR、cyclic ADPR

「サイクリックADPリボース」

　　[★]

英: cyclic ADP-ribose、cyclic ADPR、cADPR

「cADPR hydrolase」

　　[★]

cADPR加水分解酵素、cADPRヒドロラーゼ、サイクリックADPリボースヒドロラーゼ

関: ADP-ribosyl cyclase、ADPR cyclase、cyclic ADP-ribose hydrolase

「cADPRヒドロラーゼ」

　　[★]

英: cADPR hydrolase
関: サイクリックADPリボースヒドロラーゼ、cADPR加水分解酵素

「cADPR加水分解酵素」

　　[★]

英: cADPR hydrolase
関: サイクリックADPリボースヒドロラーゼ、cADPRヒドロラーゼ

[1] Lee HC, Walseth TF, Bratt GT, Hayes RN, Clapper DL (1989). "Structural determination of a cyclic metabolite of NAD⁺ with intracellular Ca²⁺-mobilizing activity". J. Biol. Chem. 264 (3): 1608–15. PMID 2912976.

[2] Lee HC, Aarhus R, Levitt D (1994). "The crystal structure of cyclic ADP-ribose". Nat. Struct. Biol. 1 (3): 143–4. doi:10.1038/nsb0394-143. PMID 7656029.

[3] Guse AH (2004). "Regulation of calcium signaling by the second messenger cyclic adenosine diphosphoribose (cADPR)". Curr. Mol. Med. 4 (3): 239–48. doi:10.2174/1566524043360771. PMID 15101682.

[4] Lukyanenko V, Györke I, Wiesner TF, Györke S. 2001. Potentiation of Ca(2+) release by cADP-ribose in the heart is mediated by enhanced ER Ca2+ uptake into the sarcoplasmic reticulum. Circ Res. 89(7):614-22. PMID 11577027; 10.1161/hh1901.098066

[5] Prasad GS, McRee DE, Stura EA, Levitt DG, Lee HC, Stout CD (1996). "Crystal structure of Aplysia ADP-ribosyl cyclase, a homolog of the bifunctional ectozyme CD38". Nat. Struct. Biol. 3 (11): 957–64. doi:10.1038/nsb1196-957. PMID 8901875.

[6] Liu Q, Kriksunov IA, Graeff R, Munshi C, Lee HC, Hao Q (2005). "Crystal structure of the human CD38 extracellular domain". Structure 13 (9): 1331–9. doi:10.1016/j.str.2005.05.012. PMID 16154090.

[7] Guse AH (2004). "Biochemistry, biology, and pharmacology of cyclic adenosine diphosphoribose (cADPR)". Curr. Med. Chem. 11 (7): 847–55. doi:10.2174/0929867043455602. PMID 15078169.

[8] Canales J, Fernández A, Rodrigues JR, Ferreira R, Ribeiro JM, Cabezas A, Costas MJ, Cameselle JC (2009). "Hydrolysis of the phosphoanhydride linkage of cyclic ADP-ribose by the Mn²⁺-dependent ADP-ribose/CDP-alcohol pyrophosphatase". FEBS Lett. 583 (10): 1593–8. doi:10.1016/j.febslet.2009.04.023. PMID 19379742.

匿名

検索

案内

案内

cADPR