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Chemical Structure| 849214-04-6 Chemical Structure| 849214-04-6

Structure of cGAMP
CAS No.: 849214-04-6

Chemical Structure| 849214-04-6

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cGAMP, an endogenous second messenger, can induce the formation of cytokines and promote innate immune response. It also acts as an activator of STING with antitumor activity.

Synonyms: Cyclic GMP-AMP; 3',3'-cGAMP

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Product Details of cGAMP

CAS No. :849214-04-6
Formula : C20H24N10O13P2
M.W : 674.41
SMILES Code : O=P(O[C@H]1[C@@H](O)[C@H](N2C=NC3=C2N=CN=C3N)O[C@@H]1COP4(O)=O)(O)OC[C@@H]5[C@@H](O4)[C@@H](O)[C@H](N6C=NC7=C6N=C(N)NC7=O)O5
Synonyms :
Cyclic GMP-AMP; 3',3'-cGAMP
MDL No. :N/A
InChI Key :RFCBNSCSPXMEBK-INFSMZHSSA-N
Pubchem ID :135471108

Safety of cGAMP

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.48mL

0.30mL

0.15mL

7.41mL

1.48mL

0.74mL

14.83mL

2.97mL

1.48mL

References

[1]Wu J, Sun L, et al. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA. Science. 2013 Feb 15;339(6121):826-30.

[2]Ablasser A, Schmid-Burgk JL, et al. Cell intrinsic immunity spreads to bystander cells via the intercellular transfer of cGAMP. Nature. 2013 Nov 28;503(7477):530-4.

[3]Liu Y, Jesus AA, et al. Activated STING in a vascular and pulmonary syndrome. N Engl J Med. 2014 Aug 7;371(6):507-518.

[4]Wu J, Sun L, Chen X, Du F, Shi H, Chen C, Chen ZJ. Cyclic GMP-AMP is an endogenous second messenger in innate immune signaling by cytosolic DNA. Science. 2013 Feb 15;339(6121):826-30. doi: 10.1126/science.1229963. Epub 2012 Dec 20. PMID: 23258412; PMCID: PMC3855410.

[5]Ablasser A, Schmid-Burgk JL, Hemmerling I, Horvath GL, Schmidt T, Latz E, Hornung V. Cell intrinsic immunity spreads to bystander cells via the intercellular transfer of cGAMP. Nature. 2013 Nov 28;503(7477):530-4. doi: 10.1038/nature12640. Epub 2013 Sep 29. PMID: 24077100; PMCID: PMC4142317.

[6]Liu Y, Jesus AA, Marrero B, Yang D, Ramsey SE, Sanchez GAM, Tenbrock K, Wittkowski H, Jones OY, Kuehn HS, Lee CR, DiMattia MA, Cowen EW, Gonzalez B, Palmer I, DiGiovanna JJ, Biancotto A, Kim H, Tsai WL, Trier AM, Huang Y, Stone DL, Hill S, Kim HJ, St Hilaire C, Gurprasad S, Plass N, Chapelle D, Horkayne-Szakaly I, Foell D, Barysenka A, Candotti F, Holland SM, Hughes JD, Mehmet H, Issekutz AC, Raffeld M, McElwee J, Fontana JR, Minniti CP, Moir S, Kastner DL, Gadina M, Steven AC, Wingfield PT, Brooks SR, Rosenzweig SD, Fleisher TA, Deng Z, Boehm M, Paller AS, Goldbach-Mansky R. Activated STING in a vascular and pulmonary syndrome. N Engl J Med. 2014 Aug 7;371(6):507-518. doi: 10.1056/NEJMoa1312625. Epub 2014 Jul 16. PMID: 25029335; PMCID: PMC4174543.

 

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