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2’,3’-cGAMP azide

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Physical properties
Molecular weight1144.14
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
1144.14
2’,3’-cGAMP azide is an excellent reagent to conjugate 2’,3’-cGAMP to alkyne-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 azide 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 mM87.402 µL437.009 µL874.019 µL4.37 mL8.74 mL
5 mM17.48 µL87.402 µL174.804 µL874.019 µL1.748 mL
10 mM8.74 µL43.701 µL87.402 µL437.009 µL874.019 µL

Molarity calculator

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

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References


View all 44 references: Citation Explorer
Microcystin-LR-induced nuclear translocation of cGAS promotes mutagenesis in human hepatocytes by impeding homologous recombination repair.
Authors: Wang, Xiaofei and Zhu, Yuchen and Lu, Wenzun and Guo, Xiaoying and Chen, Liuzeng and Zhang, Ning and Chen, Shaopeng and Ge, Chunmei and Xu, Shengmin
Journal: Toxicology letters (2023): 94-104
Responsive manganese-based nanoplatform amplifying cGAS-STING activation for immunotherapy.
Authors: He, Qingbin and Zheng, Runxiao and Ma, Junchi and Zhao, Luyang and Shi, Yafang and Qiu, Jianfeng
Journal: Biomaterials research (2023): 29
Spermidine enhances the efficacy of adjuvant in HBV vaccination in mice.
Authors: Ito, Daisuke and Ito, Hiroyasu and Ando, Tatsuya and Sakai, Yasuhiro and Ideta, Takayasu and Ishii, Ken J and Ishikawa, Tetsuya and Shimizu, Masahito
Journal: Hepatology communications (2023)
TRIM7/RNF90 promotes autophagy via regulation of ATG7 ubiquitination during L. monocytogenes infection.
Authors: Wang, Jie and Qin, Xiao and Huang, Yulu and Zhang, Qunmei and Pei, Jinyong and Wang, Yi and Goren, Idan and Ma, Shujun and Song, Zhishan and Liu, Yanzi and Xing, Hongxia and Wang, Hui and Yang, Bo
Journal: Autophagy (2023): 1-19
Cell-Free DNA Promotes Inflammation in Patients With Oral Lichen Planus via the STING Pathway.
Authors: Deng, Jing and Pan, Weiyi and Ji, Ning and Liu, Na and Chen, Qian and Chen, Jinhuan and Sun, Yutong and Xie, Liang and Chen, Qianming
Journal: Frontiers in immunology (2022): 838109
Multifaceted functions of STING in human health and disease: from molecular mechanism to targeted strategy.
Authors: Zhang, Zili and Zhou, Haifeng and Ouyang, Xiaohu and Dong, Yalan and Sarapultsev, Alexey and Luo, Shanshan and Hu, Desheng
Journal: Signal transduction and targeted therapy (2022): 394
Chemical Synthesis of the Fluorescent, Cyclic Dinucleotides cth GAMP.
Authors: Veth, Simon and Fuchs, Adrian and Özdemir, Dilara and Dialer, Clemens and Drexler, David Jan and Knechtel, Fabian and Witte, Gregor and Hopfner, Karl-Peter and Carell, Thomas and Ploetz, Evelyn
Journal: Chembiochem : a European journal of chemical biology (2022): e202200005
Liquiritigenin enhances cyclic adenosine monophosphate production to mitigate inflammation in dendritic cells.
Authors: Qin, Mingming and Guo, Aili and Li, Feng and Zhang, Fuxiang and Bi, Meirong and Zhang, Yamin and Zhu, Weiwei
Journal: International journal of immunopathology and pharmacology (2021): 20587384211038098
Synthesis and biological evaluation of all possible inosine-mixed cyclic dinucleotides that activate different hSTING variants.
Authors: Wang, Zhenghua and Zhao, Cancan and Wang, Chuanlin and Zhang, Hang and Ma, Dejun and Zhang, Qiangzhe and Wen, Xin and Li, Luyuan and Xi, Zhen
Journal: Bioorganic & medicinal chemistry (2021): 115899
Identification of a Mycobacterium tuberculosis Cyclic Dinucleotide Phosphodiesterase Inhibitor.
Authors: Karanja, Caroline W and Yeboah, Kofi S and Sintim, Herman O
Journal: ACS infectious diseases (2021): 309-317