WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 412805
CAS#: 1441190-66-4
Description: 2,3-CGAMP, or 2',3'-CGAMP, also known as Cgamp is the first cyclic di-nucleotide found in metazoa. In mammalian cells, cGAMP is synthesized by cyclic GMP-AMP synthase from ATP and GTP upon cytosolic DNA stimulation.
MedKoo Cat#: 412805
Name: 2,3-CGAMP
CAS#: 1441190-66-4
Chemical Formula: C20H24N10O13P2
Exact Mass: 674.1
Molecular Weight: 674.42
Elemental Analysis: C, 35.62; H, 3.59; N, 20.77; O, 30.84; P, 9.19
Synonym: 2,3-CGAMP; Cgamp; C-20640; C 20640; C20640; 2′-3′-cyclic GMP-AMP; cGAMP(2′→5′); Cyclic Gp(2′→5′)Ap(3′→5′);
IUPAC/Chemical Name: 2-Amino-9-((1R,6R,8R,9R,10S,15R,17R,18R)-8-(6-amino-9H-purin-9-yl)-3,9,12,18-tetrahydroxy-3,12-dioxido-2,4,7,11,13,16-hexaoxa-3,12-diphosphatricyclo(13.2.1.06,10)octadec-17-yl)-1,9-dihydro-6H-purin-6-one
InChi Key: XRILCFTWUCUKJR-INFSMZHSSA-N
InChi Code: InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
SMILES Code: O[C@H]1[C@@]2([C@@](O[C@@]1(COP(=O)(O)O[C@@]3([C@@](COP(=O)(O)O2)(O[C@]([C@@H]3O)(N4C=5C(N=C4)=C(N)N=CN5)[H])[H])[H])[H])(N6C7=C(N=C6)C(=O)N=C(N)N7)[H])[H]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 674.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Swanson KV, Junkins RD, Kurkjian CJ, Holley-Guthrie E, Pendse AA, El Morabiti R, Petrucelli A, Barber GN, Benedict CA, Ting JP. A noncanonical function of cGAMP in inflammasome priming and activation. J Exp Med. 2017 Dec 4;214(12):3611-3626. doi: 10.1084/jem.20171749. Epub 2017 Oct 13. PMID: 29030458; PMCID: PMC5716045.
2: Li T, Chen ZJ. The cGAS-cGAMP-STING pathway connects DNA damage to inflammation, senescence, and cancer. J Exp Med. 2018 May 7;215(5):1287-1299. doi: 10.1084/jem.20180139. Epub 2018 Apr 5. PMID: 29622565; PMCID: PMC5940270.
3: Ritchie C, Cordova AF, Hess GT, Bassik MC, Li L. SLC19A1 Is an Importer of the Immunotransmitter cGAMP. Mol Cell. 2019 Jul 25;75(2):372-381.e5. doi: 10.1016/j.molcel.2019.05.006. Epub 2019 May 21. PMID: 31126740; PMCID: PMC6711396.
4: Schwede F, Genieser HG, Rentsch A. The Chemistry of the Noncanonical Cyclic Dinucleotide 2'3'-cGAMP and Its Analogs. Handb Exp Pharmacol. 2017;238:359-384. doi: 10.1007/164_2015_43. PMID: 27392950.
5: Gentili M, Kowal J, Tkach M, Satoh T, Lahaye X, Conrad C, Boyron M, Lombard B, Durand S, Kroemer G, Loew D, Dalod M, Théry C, Manel N. Transmission of innate immune signaling by packaging of cGAMP in viral particles. Science. 2015 Sep 11;349(6253):1232-6. doi: 10.1126/science.aab3628. Epub 2015 Jul 30. PMID: 26229115.
6: Li T, Cheng H, Yuan H, Xu Q, Shu C, Zhang Y, Xu P, Tan J, Rui Y, Li P, Tan X. Antitumor Activity of cGAMP via Stimulation of cGAS-cGAMP-STING-IRF3 Mediated Innate Immune Response. Sci Rep. 2016 Jan 12;6:19049. doi: 10.1038/srep19049. PMID: 26754564; PMCID: PMC4709567.
7: Bai J, Liu F. The cGAS-cGAMP-STING Pathway: A Molecular Link Between Immunity and Metabolism. Diabetes. 2019 Jun;68(6):1099-1108. doi: 10.2337/dbi18-0052. PMID: 31109939; PMCID: PMC6610018.
8: Bai J, Cervantes C, Liu J, He S, Zhou H, Zhang B, Cai H, Yin D, Hu D, Li Z, Chen H, Gao X, Wang F, O'Connor JC, Xu Y, Liu M, Dong LQ, Liu F. DsbA-L prevents obesity-induced inflammation and insulin resistance by suppressing the mtDNA release-activated cGAS-cGAMP-STING pathway. Proc Natl Acad Sci U S A. 2017 Nov 14;114(46):12196-12201. doi: 10.1073/pnas.1708744114. Epub 2017 Oct 30. PMID: 29087318; PMCID: PMC5699051.
9: Eaglesham JB, Pan Y, Kupper TS, Kranzusch PJ. Viral and metazoan poxins are cGAMP-specific nucleases that restrict cGAS-STING signalling. Nature. 2019 Feb;566(7743):259-263. doi: 10.1038/s41586-019-0928-6. Epub 2019 Feb 6. Erratum in: Nature. 2019 May 13;: PMID: 30728498; PMCID: PMC6640140.
10: Chen Q, Boire A, Jin X, Valiente M, Er EE, Lopez-Soto A, Jacob L, Patwa R, Shah H, Xu K, Cross JR, Massagué J. Carcinoma-astrocyte gap junctions promote brain metastasis by cGAMP transfer. Nature. 2016 May 26;533(7604):493-498. doi: 10.1038/nature18268. Epub 2016 May 18. Erratum in: Nature. 2017 Apr 6;544(7648):124. PMID: 27225120; PMCID: PMC5021195.
