7(9)H-purin-6-ylamine/Ade/1H-Purine-6-amine/1H-Purine, 6-amino-/Vitamin- B4/Adenin/1,9-Dihydro-6H-purin-6-imine/9H-Purine-6-amine/adensoine/Crytidine/6H-Purin-6-imine, 1,9-dihydro-/1H-Purin-6-amine/9H-Purin-6-yl-amin/9H-Purin-6-amin/9H-Adenine/T56 BM DN FN HNJ IZ/Leuco-4/4-26-00-03561/9H-Purin-6-amine/Adenine/ADENINE(P)/usafcb-18/6-aminopurine/6-amino-Purine/Vitamin B4
Adenine is a purine derivative and a nucleobase with a variety of roles in biochemistry. Target: Nucleoside antimetabolite/analogAdenine is a nucleobase with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), andprotein synthesis, as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.In older literature, adenine was sometimes called Vitamin B4. It is no longer considered a true vitamin or part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), respectively. Hermann Emil Fischer was one of the early scientists to study adenine. Experiments performed in 1961 by Joan Oro have shown that a large quantity of adenine can be synthesized from the polymerization of ammonia with fivehydrogen cyanide (HCN) molecules in aqueous solution, whether this has implications for the origin of life on Earth is under debate.
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DNA N6-methyladenine (6mA) protects against restriction enzymes in bacteria. However, isolated reports have suggested additional activities and its presence in other organisms, such as unicellular eukaryotes. New data now find that 6mA may have a gene regulatory function in green alga, worm, and fly, suggesting m6A as a potential “epigenetic” mark.
Copyright © 2015 Elsevier Inc. All rights reserved.
An Adenine Code for DNA: A Second Life for N6-Methyladenine.
Heyn H1, Esteller M2.
2015 May 7
A DNA modification-methylation of cytosines and adenines-has important roles in diverse processes such as regulation of gene expression and genome stability, yet until recently adenine methylation had been considered to be only a hallmark of prokaryotes. A new study identifies abundant adenine methylation of transcriptionally active genes in early-diverging fungi that, together with recent other work, emphasizes the importance of adenine methylation in eukaryotes.
Adenine N6-methylation in diverse fungi.
2017 May 26
Background: Adenine exhibits potential anticancer activity against several types of malignancies. However, whether adenine has anticancer effects on hepatocellular carcinoma (HCC) cells is incompletely explored. Methods: Human HCC cell lines HepG2 and SK-Hep-1 (p53-wild type) and Hep3B (p53-deficient) were used as cell model. Cell growth and cell cycle distribution were determined using MTT assay and flow cytometric analysis, respectively. Protein expression and phosphorylation were assessed by Western blot. Involvement of AMP-activated protein kinase (AMPK) was evaluated using specific inhibitor and small inhibitory RNA (siRNA). Results: Adenine treatments (0.5 – 2 mM) clearly decreased the cell growth of Hep G2 and SK-Hep-1 cells to 72.5 ± 3.4% and 71.3 ± 4.6% of control, respectively. In parallel, adenine also induced sub-G1 and S phase accumulation in both HCC cells. However, adenine did not affect the cell growth and cell cycle distribution of Hep3B cell. Western blot analysis showed that adenine reduced expression of cyclin A/D1 and cyclin-dependent kinase (CDK)2 and upregulated p53, p21, Bax, PUMA, and NOXA in HepG2 cell. Moreover, adenine induced AMPK activation that was involved in the p53-associated apoptotic cascade in HepG2 cells. Inhibition of AMPK activation or knockdown of AMPK restored the decreased cell growth of HepG2 and SK-Hep-1 cells in response to adenine. Conclusions: These findings reveal that adenine reduces the cell growth of HepG2 and SK-Hep-1 but not Hep3B cells, attributing to the AMPK/p53-mediated S phase arrest and apoptosis. It suggests that adenine has anticancer potential against p53-wild type HCC cells and may be beneficial as an adjuvant for HCC treatment.
© The author(s).
AMPK; Bax; adenine; apoptosis; hepatocellular cell; p21; p53
Adenine inhibits growth of hepatocellular carcinoma cells via AMPK-mediated S phase arrest and apoptotic cascade.
Su WW1, Huang JY2, Chen HM3, Lin JT4, Kao SH2,5,6.
2020 Feb 24