c-di-AMP - CAS 54447-84-6
Catalog number:
54447-84-6
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H22N10O12P2 .2Na
Molecular Weight:
702.38
COA:
Inquire
Targets:
Adenosine A2a | Others
Description:
A2A inverse agonist; Also endogenous STING and DDX41 agonist
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Brife Description:
A2A inverse agonist; Also endogenous STING and DDX41 agonist
Appearance:
White lyophilised solid
Synonyms:
Cyclic di-adenylate monophosphate, c-di-AMP sodium salt
Solubility:
50 mg/ml in water
Storage:
Store at -20°C
MSDS:
Inquire
Quality Standard:
In-house
Quantity:
Milligrams-Grams
InChIKey:
PDXMFTWFFKBFIN-UHFFFAOYSA-N
InChI:
1S/C20H24N10O12P2/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26)
Canonical SMILES:
C1C2C(C(C(O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C6N=CN=C7N)O)OP(=O)(O1)O)O
1.[Cloning, expression, and purification of c-di-AMP metabolism-related genes from Porphyromonas gingivalis].
Wei Q, Xingqun C, Xuedong Z, Yuqing L. Hua Xi Kou Qiang Yi Xue Za Zhi. 2015 Dec;33(6):607-12.
OBJECTIVE: To clone, express, and purify cyclic diadenosine monophosphate (c-di-AMP) metabolism-related genes from Porphyromonas gingivalis (P. gingivalis) ATCC33277.
2.Too much of a good thing: regulated depletion of c-di-AMP in the bacterial cytoplasm.
Huynh TN1, Woodward JJ2. Curr Opin Microbiol. 2016 Apr;30:22-9. doi: 10.1016/j.mib.2015.12.007. Epub 2016 Jan 7.
Bacteria that synthesize c-di-AMP also encode several mechanisms for controlling c-di-AMP levels within the cytoplasm. One major class of phosphodiesterases comprises GdpP and DhhP homologs, which degrade c-di-AMP into the linear molecule 5'-pApA or AMP by the DHH-DHHA1 domain. The other major class comprises PgpH homologs, which degrade c-di-AMP by the HD domain. Both GdpP and PgpH harbor sensory domains, likely to regulate c-di-AMP hydrolysis activity in response to signal input. As another possible mechanism for controlling cytoplasmic c-di-AMP levels, bacteria also secrete c-di-AMP via multidrug resistance transporters, as demonstrated for Listeria monocytogenes. Mutants that accumulate high c-di-AMP levels, by deletion of phosphodiesterases or multidrug resistance transporters, exhibit aberrant physiology, growth defects, and attenuated virulence in infection.
3.Nuclease-Resistant c-di-AMP Derivatives That Differentially Recognize RNA and Protein Receptors.
Meehan RE, Torgerson CD, Gaffney BL1, Jones RA1, Strobel SA. Biochemistry. 2016 Feb 16;55(6):837-49. doi: 10.1021/acs.biochem.5b00965. Epub 2016 Feb 3.
The ability of bacteria to sense environmental cues and adapt is essential for their survival. The use of second-messenger signaling molecules to translate these cues into a physiological response is a common mechanism employed by bacteria. The second messenger 3'-5'-cyclic diadenosine monophosphate (c-di-AMP) has been linked to a diverse set of biological processes involved in maintaining cell viability and homeostasis, as well as pathogenicity. A complex network of both protein and RNA receptors inside the cell activates specific pathways and mediates phenotypic outputs in response to c-di-AMP. Structural analysis of these RNA and protein receptors has revealed the different recognition elements employed by these effectors to bind the same small molecule. Herein, using a series of c-di-AMP analogues, we probed the interactions made with a riboswitch and a phosphodiesterase protein to identify the features important for c-di-AMP binding and recognition.
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CAS 54447-84-6 c-di-AMP

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