30377-37-8
Chemical Structure
2,8-Dihydroxyadenine
- CAS No.: 30377-37-8
- Formula:C5H5N5O2
- Molecular Weight:167.13
IUPAC Name: 6-amino-7,9-dihydro-2H-purine-2,8(3H)-dione
InChIKey: XFBOJHLYDJZYSP-UHFFFAOYSA-N
SMILES: O=C1NC2=C(NC(N2)=O)C(N)=N1
Biological Activity: 2,8-Dihydroxyadenine is an endogenous metabolite that forms crystals in urine, leading to kidney stone formation and crystal deposition in the kidney. 2,8-Dihydroxyadenine induces crystal-induced tubular injury, inflammation, and fibrosis through crystal deposition in renal tubules, where crystals are excreted in urine, internalized by tubular epithelial cells, and transported to the interstitium. 2,8-Dihydroxyadenine upregulates CD44 expression near crystals, TNF-α signaling through NF-κB, and mTORC1 signaling, while inducing actin stress fiber formation and cytoskeletal remodeling. 2,8-Dihydroxyadenine downregulates epithelial-mesenchymal transition pathways and oxidative phosphorylation, and induces changes affecting inflammation, metabolism, and cell cycle regulation. 2,8-Dihydroxyadenine can be used in research on kidney disease, adenine phosphoribosyltransferase deficiency, and kidney stone disease[1][2][3][4][5][6].
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2,8-Dihydroxyadenine | 2,8-Dihydroxyadenine is an endogenous metabolite that forms crystals in urine, leading to kidney stone formation and crystal deposition in the kidney. 2,8-Dihydroxyadenine induces crystal-induced tubular injury, inflammation, and fibrosis through crystal deposition in renal tubules, where crystals are excreted in urine, internalized by tubular epithelial cells, and transported to the interstitium. 2,8-Dihydroxyadenine upregulates CD44 expression near crystals, TNF-α signaling through NF-κB, and mTORC1 signaling, while inducing actin stress fiber formation and cytoskeletal remodeling. 2,8-Dihydroxyadenine downregulates epithelial-mesenchymal transition pathways and oxidative phosphorylation, and induces changes affecting inflammation, metabolism, and cell cycle regulation. 2,8-Dihydroxyadenine can be used in research on kidney disease, adenine phosphoribosyltransferase deficiency, and kidney stone disease. | |||||||||||||||||||||
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References
- [1]. Klinkhammer BM, et al. Cellular and Molecular Mechanisms of Kidney Injury in 2,8-Dihydroxyadenine Nephropathy. Journal of the American Society of Nephrology : JASN. 2020 Apr;31(4):799-816.
- [2]. Diculescu VC, et al. Electrochemical behaviour of 2,8-dihydroxyadenine at a glassy carbon electrode. Bioelectrochemistry (Amsterdam, Netherlands). 2007 Jan;70(1):141-6.
- [3]. Helgudottir HR, et al. 2,8-Dihydroxyadenine disrupts epithelial integrity and alters kidney cell phenotype in vitro. Journal of molecular medicine (Berlin, Germany). 2026 Jan 06;104(1):23.
- [4]. Thorsteinsdottir M, et al. Quantitative UPLC-MS/MS assay of urinary 2,8-dihydroxyadenine for diagnosis and management of adenine phosphoribosyltransferase deficiency. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2016 Nov 15;1036-1037:170-177.
- [5]. Thorsteinsdottir UA, et al. Correlation of Plasma and Urine 2,8-Dihydroxyadenine and Adenine and Clinical Characteristics in Individuals With Adenine Phosphoribosyltransferase Deficiency. Journal of inherited metabolic disease. 2025 Jul;48(4):e70054.
- [6]. Engle SJ, et al. Adenine phosphoribosyltransferase-deficient mice develop 2,8-dihydroxyadenine nephrolithiasis. Proceedings of the National Academy of Sciences of the United States of America. 1996 May 28;93(11):5307-12.
