72496-59-4
Chemical Structure
Queuine
- CAS No.: 72496-59-4
- Formula:C12H15N5O3
- Molecular Weight:277.28
IUPAC Name: 2-amino-5-((((1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl)amino)methyl)-1,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one
InChIKey: WYROLENTHWJFLR-ACLDMZEESA-N
SMILES: O[C@@H]([C@H](C=C1)O)[C@H]1NCC2=CNC(NC(N)=N3)=C2C3=O
Biological Activity: Queuine is a selective substrate for tRNA guanine transglycosylase (TGT) and can be incorporated into eukaryotic tRNA. Queuine promotes tRNA modification, affecting mitochondrial function and Warburg metabolic phenotype. If Queuine is deficient, aerobic glycolysis can be enhanced, oxidative phosphorylation can be inhibited, and Warburg metabolism can be promoted, accompanied by increased ammonia and lactate production and increased lactate dehydrogenase activity. Queuine can be used for autoimmune diseases (such as experimental models of multiple sclerosis) and cancer metabolic regulation, and its deficiency is associated with low tRNA modification in tumor cells[1][2][3].
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Queuine | 99.74% | Queuine is a selective substrate for tRNA guanine transglycosylase (TGT) and can be incorporated into eukaryotic tRNA. Queuine promotes tRNA modification, affecting mitochondrial function and Warburg metabolic phenotype. If Queuine is deficient, aerobic glycolysis can be enhanced, oxidative phosphorylation can be inhibited, and Warburg metabolism can be promoted, accompanied by increased ammonia and lactate production and increased lactate dehydrogenase activity. Queuine can be used for autoimmune diseases (such as experimental models of multiple sclerosis) and cancer metabolic regulation, and its deficiency is associated with low tRNA modification in tumor cells. | ||||||||||||||||||||
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- [1]. Yifeng Yuan, et al. Discovery of novel bacterial queuine salvage enzymes and pathways in human pathogens. Proc Natl Acad Sci U S A. 2019 Sep 17;116(38):19126-19135. [Content Brief]
- [2]. Hayes P, et al. Queuine Micronutrient Deficiency Promotes Warburg Metabolism and Reversal of the Mitochondrial ATP Synthase in Hela Cells. Nutrients. 2020 Mar 24;12(3):871. [Content Brief]
- [3]. Varghese S, et al. In vivo modification of tRNA with an artificial nucleobase leads to full disease remission in an animal model of multiple sclerosis. Nucleic Acids Res. 2017 Feb 28;45(4):2029-2039. [Content Brief]
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