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MedKoo Cat#: 555921 | Name: cGAMP free acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cyclic AMP-GMP, also known as cGAMP, is one of several naturally occurring cyclic dinucleotides that act as a bacterial second messengers to regulate important signaling mechanisms in prokaryotes that control bacterial survival, adhesion, colonization, biofilm formation, and virulence factors production. In cholera c-AMP-GMP promotes intestinal colonization by down-regulating chemotaxis. During infections bacterial cGAMP is bound by host STING (stimulator of interferon genes) activating innate immune responses leading to expression of interferon genes.

Chemical Structure

cGAMP free acid
cGAMP free acid
CAS#849214-04-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 555921

Name: cGAMP free acid

CAS#: 849214-04-6 (free acid)

Chemical Formula: C20H24N10O13P2

Exact Mass: 674.1000

Molecular Weight: 674.42

Elemental Analysis: C, 35.62; H, 3.59; N, 20.77; O, 30.84; P, 9.19

Price and Availability

Size Price Availability Quantity
50mg USD 1,650.00 2 Weeks
100mg USD 2,750.00 2 Weeks
200mg USD 3,750.00 2 Weeks
500mg USD 5,750.00 2 Weeks
1g USD 7,650.00 2 Weeks
2g USD 9,950.00 2 Weeks
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Related CAS #
849214-04-6 (free acid) 2407516-83-8 (sodium)
Synonym
3′3′-cGAMP; Cyclic AMP-GMP; c-GMP-AMP; cyclic GMP-AMP; cGAMP;
IUPAC/Chemical Name
2-amino-9-((2R,3R,3aS,7aR,9R,10R,10aS,14aR)-9-(6-amino-9H-purin-9-yl)-3,5,10,12-tetrahydroxy-5,12-dioxidooctahydro-2H,7H-difuro[3,2-d:3',2'-j][1,3,7,9]tetraoxa[2,8]diphosphacyclododecin-2-yl)-3,9-dihydro-6H-purin-6-one
InChi Key
RFCBNSCSPXMEBK-INFSMZHSSA-N
InChi Code
InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-10(31)12-6(40-18)1-38-45(36,37)43-13-7(2-39-44(34,35)42-12)41-19(11(13)32)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=C1N=C(NC2=C1N=CN2[C@@H]3O[C@H](COP(O)(O[C@H]4[C@H]([C@@H](O[C@@H]4CO5)N6C=NC7=C6N=CN=C7N)O)=O)[C@@H](OP5(O)=O)[C@H]3O)N
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
to be determined
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
More Info
Solvent mg/mL mM
Solubility
To be determined 0.0 0.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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: Vassilieva EV, Li S, Korniychuk H, Taylor DM, Wang S, Prausnitz MR, Compans RW. cGAMP/Saponin Adjuvant Combination Improves Protective Response to Influenza Vaccination by Microneedle Patch in an Aged Mouse Model. Front Immunol. 2021 Feb 2;11:583251. doi: 10.3389/fimmu.2020.583251. PMID: 33603732; PMCID: PMC7884748. 2: Lai J, Fu Y, Tian S, Huang S, Luo X, Lin L, Zhang X, Wang H, Lin Z, Zhao H, Lin S, Zhao J, Xu S, Li D, Cai S, Dong L, Qian J, Liang J, Li Q, Zhang Y, Fan J, Balderas R, Chen Q. Zebularine elevates STING expression and enhances cGAMP cancer immunotherapy in mice. Mol Ther. 2021 Feb 9:S1525-0016(21)00072-1. doi: 10.1016/j.ymthe.2021.02.005. Epub ahead of print. PMID: 33571681. 3: Nagata M, Kosaka A, Yajima Y, Yasuda S, Ohara M, Ohara K, Harabuchi S, Hayashi R, Funakoshi H, Ueda J, Kumai T, Nagato T, Oikawa K, Harabuchi Y, Esteban C, Ohkuri T, Kobayashi H. A critical role of STING-triggered tumor- migrating neutrophils for anti-tumor effect of intratumoral cGAMP treatment. Cancer Immunol Immunother. 2021 Jan 28. doi: 10.1007/s00262-021-02864-0. Epub ahead of print. PMID: 33507344. 4: Dorostkar F, Arashkia A, Roohvand F, Shoja Z, Navari M, Mashhadi Abolghasem Shirazi M, Shahosseini Z, Farahmand M, Shams Nosrati MS, Jalilvand S. Co- administration of 2'3'-cGAMP STING activator and CpG-C adjuvants with a mutated form of HPV 16 E7 protein leads to tumor growth inhibition in the mouse model. Infect Agent Cancer. 2021 Jan 26;16(1):7. doi: 10.1186/s13027-021-00346-7. PMID: 33499895; PMCID: PMC7836183. 5: Li J, Duran MA, Dhanota N, Chatila WK, Bettigole SE, Kwon J, Sriram RK, Humphries MP, Salto-Tellez M, James JA, Hanna MG, Melms JC, Vallabhaneni S, Litchfield K, Usaite I, Biswas D, Bareja R, Li HW, Martin ML, Dorsaint P, Cavallo JA, Li P, Pauli C, Gottesdiener L, DiPardo BJ, Hollmann TJ, Merghoub T, Wen HY, Reis-Filho JS, Riaz N, Su SM, Kalbasi A, Vasan N, Powell SN, Wolchok JD, Elemento O, Swanton C, Shoushtari AN, Parkes EE, Izar B, Bakhoum SF. Metastasis and immune evasion from extracellular cGAMP hydrolysis. Cancer Discov. 2020 Dec 28:CD-20-0387. doi: 10.1158/2159-8290.CD-20-0387. Epub ahead of print. PMID: 33372007. 6: Cai H, Holleufer A, Simonsen B, Schneider J, Lemoine A, Gad HH, Huang J, Huang J, Chen D, Peng T, Marques JT, Hartmann R, Martins NE, Imler JL. 2'3'-cGAMP triggers a STING- and NF-κB-dependent broad antiviral response in Drosophila. Sci Signal. 2020 Dec 1;13(660):eabc4537. doi: 10.1126/scisignal.abc4537. PMID: 33262294. 7: Xie X, Liu J, Wang X. Design, Synthesis and Biological Evaluation of (2',5' and 3'5'-Linked) cGAMP Analogs that Activate Stimulator of Interferon Genes (STING). Molecules. 2020 Nov 12;25(22):5285. doi: 10.3390/molecules25225285. PMID: 33198423; PMCID: PMC7697705. 8: Eaglesham JB, McCarty KL, Kranzusch PJ. Structures of diverse poxin cGAMP nucleases reveal a widespread role for cGAS-STING evasion in host-pathogen conflict. Elife. 2020 Nov 16;9:e59753. doi: 10.7554/eLife.59753. PMID: 33191912; PMCID: PMC7688311. 9: Lahey LJ, Mardjuki RE, Wen X, Hess GT, Ritchie C, Carozza JA, Böhnert V, Maduke M, Bassik MC, Li L. LRRC8A:C/E Heteromeric Channels Are Ubiquitous Transporters of cGAMP. Mol Cell. 2020 Nov 19;80(4):578-591.e5. doi: 10.1016/j.molcel.2020.10.021. Epub 2020 Nov 9. PMID: 33171122. 10: Campisi M, Sundararaman SK, Shelton SE, Knelson EH, Mahadevan NR, Yoshida R, Tani T, Ivanova E, Cañadas I, Osaki T, Lee SWL, Thai T, Han S, Piel BP, Gilhooley S, Paweletz CP, Chiono V, Kamm RD, Kitajima S, Barbie DA. Tumor- Derived cGAMP Regulates Activation of the Vasculature. Front Immunol. 2020 Sep 4;11:2090. doi: 10.3389/fimmu.2020.02090. PMID: 33013881; PMCID: PMC7507350. 11: Hernáez B, Alonso G, Georgana I, El-Jesr M, Martín R, Shair KHY, Fischer C, Sauer S, Maluquer de Motes C, Alcamí A. Viral cGAMP nuclease reveals the essential role of DNA sensing in protection against acute lethal virus infection. Sci Adv. 2020 Sep 18;6(38):eabb4565. doi: 10.1126/sciadv.abb4565. PMID: 32948585; PMCID: PMC7500930. 12: Chin EN, Yu C, Vartabedian VF, Jia Y, Kumar M, Gamo AM, Vernier W, Ali SH, Kissai M, Lazar DC, Nguyen N, Pereira LE, Benish B, Woods AK, Joseph SB, Chu A, Johnson KA, Sander PN, Martínez-Peña F, Hampton EN, Young TS, Wolan DW, Chatterjee AK, Schultz PG, Petrassi HM, Teijaro JR, Lairson LL. Antitumor activity of a systemic STING-activating non-nucleotide cGAMP mimetic. Science. 2020 Aug 21;369(6506):993-999. doi: 10.1126/science.abb4255. PMID: 32820126. 13: Zhao Z, Ma Z, Wang B, Guan Y, Su XD, Jiang Z. Mn2+ Directly Activates cGAS and Structural Analysis Suggests Mn2+ Induces a Noncanonical Catalytic Synthesis of 2'3'-cGAMP. Cell Rep. 2020 Aug 18;32(7):108053. doi: 10.1016/j.celrep.2020.108053. PMID: 32814054. 14: Carozza JA, Brown JA, Böhnert V, Fernandez D, AlSaif Y, Mardjuki RE, Smith M, Li L. Structure-Aided Development of Small-Molecule Inhibitors of ENPP1, the Extracellular Phosphodiesterase of the Immunotransmitter cGAMP. Cell Chem Biol. 2020 Nov 19;27(11):1347-1358.e5. doi: 10.1016/j.chembiol.2020.07.007. Epub 2020 Jul 28. PMID: 32726585; PMCID: PMC7680421. 15: Cheng H, Xu Q, Lu X, Yuan H, Li T, Zhang Y, Tan X. Activation of STING by cGAMP Regulates MDSCs to Suppress Tumor Metastasis via Reversing Epithelial-Mesenchymal Transition. Front Oncol. 2020 Jun 11;10:896. doi: 10.3389/fonc.2020.00896. PMID: 32596152; PMCID: PMC7300176. 16: He Y, Hong C, Yan EZ, Fletcher SJ, Zhu G, Yang M, Li Y, Sun X, Irvine DJ, Li J, Hammond PT. Self-assembled cGAMP-STINGΔTM signaling complex as a bioinspired platform for cGAMP delivery. Sci Adv. 2020 Jun 12;6(24):eaba7589. doi: 10.1126/sciadv.aba7589. PMID: 32582856; PMCID: PMC7292616. 17: Su CI, Kao YT, Chang CC, Chang Y, Ho TS, Sun HS, Lin YL, Lai MMC, Liu YH, Yu CY. DNA-induced 2'3'-cGAMP enhances haplotype-specific human STING cleavage by dengue protease. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):15947-15954. doi: 10.1073/pnas.1922243117. Epub 2020 Jun 23. PMID: 32576686; PMCID: PMC7354927. 18: Lim J, Kim HY. Novel Applications of Biocatalysis to Stereochemistry Determination of 2'3'-cGAMP Bisphosphorothioate (2'3'-cGSASMP). ACS Omega. 2020 Jun 3;5(23):14173-14179. doi: 10.1021/acsomega.0c01942. PMID: 32566885; PMCID: PMC7301576. 19: Wiser C, Kim B, Vincent J, Ascano M. Small molecule inhibition of human cGAS reduces total cGAMP output and cytokine expression in cells. Sci Rep. 2020 May 5;10(1):7604. doi: 10.1038/s41598-020-64348-y. PMID: 32371942; PMCID: PMC7200739. 20: Ritchie C, Li L. cGAMP as an Adjuvant in Antiviral Vaccines and Cancer Immunotherapy. Biochemistry. 2020 May 12;59(18):1713-1715. doi: 10.1021/acs.biochem.0c00226. Epub 2020 Apr 17. PMID: 32301606.

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