ADP-ribose

Adenosine diphosphate ribose
Names
	Other names ADP ribose; ADPR; Adenosine 5'-diphosphoribose
Identifiers
CAS Number	20762-30-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1161865 ;
ChemSpider	388340 ;
MeSH	Adenosine+Diphosphate+Ribose
PubChem CID	439200;
UNII	XV3S4KV26E ;
	InChI InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(24)9(23)6(31-14)2-30-35(26,27)34-36(28,29)33-15-11(25)8(22)5(1-21)32-15/h3-6,8-11,14-15,21-25H,1-2H2,(H4,16,17,18,26,27,28,29)/p+1/t5-,6+,8-,9+,10+,11-,14+,15+/m0/s1 Key: YNCNQNWXUFCWJS-DKMYFHGXSA-O ; InChI=1/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(24)9(23)6(31-14)2-30-35(26,27)34-36(28,29)33-15-11(25)8(22)5(1-21)32-15/h3-6,8-11,14-15,21-25H,1-2H2,(H4,16,17,18,26,27,28,29)/p+1/t5-,6+,8-,9+,10+,11-,14+,15+/m0/s1 Key: YNCNQNWXUFCWJS-LKOYDKQFBH;
	SMILES O=P(O1O((O)1O)CO)(O)OP(=O)(OC4O(n3c2ncnc(N)c2nc3)(O)4O)O;
Properties
Chemical formula	C15H23N5O14P2
Molar mass	559.316 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). verify (what is ?) Infobox references

Adenosine diphosphate ribose (ADPR) is an ester molecule formed into chains by the enzyme poly ADP ribose polymerase.^[1] ADPR is created from cyclic ADP-ribose (cADPR) by the CD38 enzyme using nicotinamide adenine dinucleotide (NAD⁺) as a cofactor.^[1]

ADPR binds to and activates the TRPM2 ion channel.^[2] ADPR is the most potent agonist of the TRPM2 channel.^[3] cADPR also binds to TPRM2, and the action of both molecules is synergistic, with both molecules enhancing the action of the other molecule in activating the TRPM2 channel.^[4] Researchers are not sure how the Adenosine diphosphate reacts with the TRPM2 channel, but the ribose sugar may play a role in activating the TRPM2 ion channel.^[5]

References

^ ^a ^b Braidy N, Berg J, Clement J, Sachdev P (2019). "Role of Nicotinamide Adenine Dinucleotide and Related Precursors as Therapeutic Targets for Age-Related Degenerative Diseases: Rationale, Biochemistry, Pharmacokinetics, and Outcomes". Antioxidants & Redox Signaling. 10 (2): 251–294. doi:10.1089/ars.2017.7269. PMC 6277084. PMID 29634344.
^ Fonfria E, Marshall IC, Benham CD, et al. (September 2004). "TRPM2 channel opening in response to oxidative stress is dependent on activation of poly(ADP-ribose) polymerase". Br. J. Pharmacol. 143 (1): 186–92. doi:10.1038/sj.bjp.0705914. PMC 1575275. PMID 15302683.
^ Yu P, Cai X, Liang Y, Yang W (2019). "Roles of NAD + and Its Metabolites Regulated Calcium Channels in Cancer". Molecules. 25 (20): 4826. doi:10.3390/molecules25204826. PMC 7587972. PMID 33092205.
^ Lee HC (2011). "Cyclic ADP-ribose and NAADP: fraternal twin messengers for calcium signaling". Science China Life Sciences. 54 (8): 699–711. doi:10.1007/s11427-011-4197-3. PMID 21786193. S2CID 24286381.
^ Baszczyňski, Ondřej; Watt, Joanna M.; Rozewitz, Monika D.; Guse, Andreas H.; Fliegert, Ralf; Potter, Barry V. L. (2019). "Synthesis of Terminal Ribose Analogues of Adenosine 5′-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2". The Journal of Organic Chemistry. 84 (10): 6143–6157. doi:10.1021/acs.joc.9b00338. PMC 6528165. PMID 30978018.

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[pmid29634344-1] Braidy N, Berg J, Clement J, Sachdev P (2019). "Role of Nicotinamide Adenine Dinucleotide and Related Precursors as Therapeutic Targets for Age-Related Degenerative Diseases: Rationale, Biochemistry, Pharmacokinetics, and Outcomes". Antioxidants & Redox Signaling. 10 (2): 251–294. doi:10.1089/ars.2017.7269. PMC 6277084. PMID 29634344.

[pmid15302683-2] Fonfria E, Marshall IC, Benham CD, et al. (September 2004). "TRPM2 channel opening in response to oxidative stress is dependent on activation of poly(ADP-ribose) polymerase". Br. J. Pharmacol. 143 (1): 186–92. doi:10.1038/sj.bjp.0705914. PMC 1575275. PMID 15302683.

[pmid33092205-3] Yu P, Cai X, Liang Y, Yang W (2019). "Roles of NAD + and Its Metabolites Regulated Calcium Channels in Cancer". Molecules. 25 (20): 4826. doi:10.3390/molecules25204826. PMC 7587972. PMID 33092205.

[pmid21786193-4] Lee HC (2011). "Cyclic ADP-ribose and NAADP: fraternal twin messengers for calcium signaling". Science China Life Sciences. 54 (8): 699–711. doi:10.1007/s11427-011-4197-3. PMID 21786193. S2CID 24286381.

[5] Baszczyňski, Ondřej; Watt, Joanna M.; Rozewitz, Monika D.; Guse, Andreas H.; Fliegert, Ralf; Potter, Barry V. L. (2019). "Synthesis of Terminal Ribose Analogues of Adenosine 5′-Diphosphate Ribose as Probes for the Transient Receptor Potential Cation Channel TRPM2". The Journal of Organic Chemistry. 84 (10): 6143–6157. doi:10.1021/acs.joc.9b00338. PMC 6528165. PMID 30978018.

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Names



Other names ADP ribose ADPR Adenosine 5'-diphosphoribose
Identifiers
CAS Number	20762-30-5^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1161865^N
ChemSpider	388340^N
MeSH	Adenosine+Diphosphate+Ribose
PubChem CID	439200
UNII	XV3S4KV26E^Y
InChI InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(24)9(23)6(31-14)2-30-35(26,27)34-36(28,29)33-15-11(25)8(22)5(1-21)32-15/h3-6,8-11,14-15,21-25H,1-2H2,(H4,16,17,18,26,27,28,29)/p+1/t5-,6+,8-,9+,10+,11-,14+,15+/m0/s1^N Key: YNCNQNWXUFCWJS-DKMYFHGXSA-O^N InChI=1/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(24)9(23)6(31-14)2-30-35(26,27)34-36(28,29)33-15-11(25)8(22)5(1-21)32-15/h3-6,8-11,14-15,21-25H,1-2H2,(H4,16,17,18,26,27,28,29)/p+1/t5-,6+,8-,9+,10+,11-,14+,15+/m0/s1 Key: YNCNQNWXUFCWJS-LKOYDKQFBH
SMILES O=P(O1O((O)1O)CO)(O)OP(=O)(OC4O(n3c2ncnc(N)c2nc3)(O)4O)O
Properties
Chemical formula	C₁₅H₂₃N₅O₁₄P₂
Molar mass	559.316 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ^YN ?) Infobox references

See also

References