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2’,3’-cGAMP maleimide

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Physical properties
Molecular weight1156.10
SolventDMSO
Storage, safety and handling
H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22
StorageFreeze (< -15 °C); Minimize light exposure

OverviewpdfSDSpdfProtocol


Molecular weight
1156.10
2’,3’-cGAMP maleimide is an excellent reagent to covalently conjugate 2’,3’-cGAMP to thiol containing-or thiol-modified biological targets, such as proteins, peptides, and nucleic acids. 2’,3’-cGAMP has gained significant attention in recent years due to its potential as a therapeutic target for diseases such as cancer and viral infections. It has been shown to activate the immune system and enhance the efficacy of immune checkpoint inhibitors, which are a type of cancer immunotherapy. 2’,3’-cGAMP (cyclic GMP-AMP) is a cyclic dinucleotide second messenger molecule that plays a critical role in the innate immune system. It is synthesized by the enzyme cGAS (cyclic GMP-AMP synthase) in response to cytosolic DNA that has been released from damaged or infected cells. Once synthesized, 2’,3’-cGAMP binds to the adaptor protein STING (stimulator of interferon genes) and triggers downstream signaling pathways that result in the production of type I interferons and other cytokines, leading to an immune response against the invading pathogen.

Calculators


Common stock solution preparation

Table 1. Volume of DMSO needed to reconstitute specific mass of 2’,3’-cGAMP maleimide to given concentration. Note that volume is only for preparing stock solution. Refer to sample experimental protocol for appropriate experimental/physiological buffers.

0.1 mg0.5 mg1 mg5 mg10 mg
1 mM86.498 µL432.489 µL864.977 µL4.325 mL8.65 mL
5 mM17.3 µL86.498 µL172.995 µL864.977 µL1.73 mL
10 mM8.65 µL43.249 µL86.498 µL432.489 µL864.977 µL

Molarity calculator

Enter any two values (mass, volume, concentration) to calculate the third.

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References


View all 9 references: Citation Explorer
Discovery of Non-Nucleotide Small-Molecule STING Agonists via Chemotype Hybridization.
Authors: Cherney, Emily C and Zhang, Liping and Lo, Julian and Huynh, Tram and Wei, Donna and Ahuja, Vijay and Quesnelle, Claude and Schieven, Gary L and Futran, Alan and Locke, Gregory A and Lin, Zeyu and Monereau, Laura and Chaudhry, Charu and Blum, Jordan and Li, Sha and Fereshteh, Mark and Li-Wang, Bifang and Gangwar, Sanjeev and Pan, Chin and Chong, Colin and Zhu, Xiao and Posy, Shana L and Sack, John S and Zhang, Ping and Ruzanov, Max and Harner, Mary and Akhtar, Fahad and Schroeder, Gretchen M and Vite, Gregory and Fink, Brian
Journal: Journal of medicinal chemistry (2022): 3518-3538
Novel Poxin Stable cGAMP-Derivatives Are Remarkable STING Agonists.
Authors: Stazzoni, Samuele and Böhmer, Daniel F R and Hernichel, Fabian and Özdemir, Dilara and Pappa, Aikaterini and Drexler, David and Bauernfried, Stefan and Witte, Gregor and Wagner, Mirko and Veth, Simon and Hopfner, Karl-Peter and Hornung, Veit and König, Lars M and Carell, Thomas
Journal: Angewandte Chemie (International ed. in English) (2022): e202207175
cGAS/cGAMP/STING signal propagation in the tumor microenvironment: Key role for myeloid cells in antitumor immunity.
Authors: Mekers, Vera E and Kho, Vera M and Ansems, Marleen and Adema, Gosse J
Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology (2022): 158-167
Catalytic asymmetric and stereodivergent oligonucleotide synthesis.
Authors: Featherston, Aaron L and Kwon, Yongseok and Pompeo, Matthew M and Engl, Oliver D and Leahy, David K and Miller, Scott J
Journal: Science (New York, N.Y.) (2021): 702-707
Crystal structures of human ENPP1 in apo and bound forms.
Authors: Dennis, Matthew L and Newman, Janet and Dolezal, Olan and Hattarki, Meghan and Surjadi, Regina N and Nuttall, Stewart D and Pham, Tam and Nebl, Tom and Camerino, Michelle and Khoo, Poh Sim and Monahan, Brendon J and Peat, Thomas S
Journal: Acta crystallographica. Section D, Structural biology (2020): 889-898
STING Activation and its Application in Immuno-Oncology.
Authors: Lian, Yiqian and Duffy, Kevin J and Yang, Jingsong
Journal: Current topics in medicinal chemistry (2019): 2205-2227
Nucleic Acid Sensing Machinery: Targeting Innate Immune System for Cancer Therapy.
Authors: Iurescia, Sandra and Fioretti, Daniela and Rinaldi, Monica
Journal: Recent patents on anti-cancer drug discovery (2018): 2-17
Cytosolic sensing of immuno-stimulatory DNA, the enemy within.
Authors: Dhanwani, Rekha and Takahashi, Mariko and Sharma, Sonia
Journal: Current opinion in immunology (2018): 82-87
Trafficking-Mediated STING Degradation Requires Sorting to Acidified Endolysosomes and Can Be Targeted to Enhance Anti-tumor Response.
Authors: Gonugunta, Vijay K and Sakai, Tomomi and Pokatayev, Vladislav and Yang, Kun and Wu, Jianjun and Dobbs, Nicole and Yan, Nan
Journal: Cell reports (2017): 3234-3242