23567-96-6
Chemical Structure
8-Bromo-AMP
Synonym(s): 8-Bromoadenosine 5'-monophosphate; 8-Bromoadenylic acid
- CAS No.: 23567-96-6
- Formula:C10H13BrN5O7P
- Molecular Weight:426.12
IUPAC Name: ((2R,3S,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
InChIKey: DNPIJKNXFSPNNY-UUOKFMHZSA-N
SMILES: O=P(O)(OC[C@@H]1[C@H]([C@H]([C@H](N2C(Br)=NC3=C(N=CN=C32)N)O1)O)O)O
Biological Activity: 8-Bromo-AMP (8-Bromoadenosine 5'-monophosphate) is an AMP analog. 8-Bromo-AMP inhibits ADP-dependent glucokinase (ADPGK). 8-Bromo-AMP competitively inhibits ADPGK by binding to the nucleotide-binding site, inducing conformational changes, and acting on catalytic residues. 8-Bromo-AMP non-competitively inhibits rat adenylate kinase isozymes AK-M, AK II, and AK III. 8-Bromo-AMP inhibits T cell activation-induced ROS production and ROS-dependent IL-2 and IκB expression. 8-Bromo-AMP is used in research on cancer and myocardial ischemia-reperfusion injury[1][2][3][4][5][6][7][8][9][10][11][12][13].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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8-Bromo-AMP | 98.78% | 8-Bromo-AMP (8-Bromoadenosine 5'-monophosphate) is an AMP analog. 8-Bromo-AMP inhibits ADP-dependent glucokinase (ADPGK). 8-Bromo-AMP competitively inhibits ADPGK by binding to the nucleotide-binding site, inducing conformational changes, and acting on catalytic residues. 8-Bromo-AMP non-competitively inhibits rat adenylate kinase isozymes AK-M, AK II, and AK III. 8-Bromo-AMP inhibits T cell activation-induced ROS production and ROS-dependent IL-2 and IκB expression. 8-Bromo-AMP is used in research on cancer and myocardial ischemia-reperfusion injury. | ||||||||||||||||||||
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References
- [1]. Grudnik P, et al. Structural basis for ADP-dependent glucokinase inhibition by 8-bromo-substituted adenosine nucleotide. The Journal of biological chemistry. 2018 Jul 13;293(28):11088-11099.
- [2]. Lesiak K, et al. Synthesis and biological activities of oligo(8-bromoadenylates) as analogues of 5'-O-triphosphoadenylyl(2'----5')adenylyl(2'----5')adenosine. Journal of medicinal chemistry. 1986 Jun;29(6):1015-22.
- [3]. Sandnes D, et al. 8-bromo-cAMP and 8-CPT-cAMP increase the density of beta-adrenoceptors in hepatocytes by a mechanism not mimicking the effect of cAMP. Pharmacology & toxicology. 1996 Jul;79(1):15-22.
- [4]. Polya GM, et al. Regulation of a plant 5'(3')-ribonucleotide phosphohydrolase by cyclic nucleotides and pyrimidine, purine, and cytokinin ribosides. Proceedings of the National Academy of Sciences of the United States of America. 1974 Apr;71(4):1299-303.
- [5]. Niles RM, et al. Differential growth inhibition in two human carcinoma cell lines by cyclic adenosine 5'-monophosphate analogs. Journal of the National Cancer Institute. 1979 Oct;63(4):909-11.
- [6]. Shindo S, et al. A physiological role of AMP-activated protein kinase in phenobarbital-mediated constitutive androstane receptor activation and CYP2B induction. The Biochemical journal. 2007 Feb 01;401(3):735-41.
- [7]. Hai TT, et al. Species- or isozyme-specific enzyme inhibitors. 7. Selective effects in inhibitions of rat adenylate kinase isozymes by adenosine 5'-phosphate derivatives. Journal of medicinal chemistry. 1982 Jul;25(7):806-12.
- [8]. Shah MM, et al. The connexin43 gap junction protein is phosphorylated by protein kinase A and protein kinase C: in vivo and in vitro studies. Molecular and cellular biochemistry. 2002 Sep;238(1-2):57-68.
- [9]. Roberts AW, et al. Methylxanthines reversibly inhibit tracheary-element differentiation in suspension cultures of Zinnia elegans L. Planta. 1992 Mar;186(4):586-92.
- [10]. Minelli A, et al. Activity of IMP- and AMP-preferring isoforms of 5'-nucleotidase from human seminal plasma with AMP analogues. Molecular genetics and metabolism. 1999 Jan;66(1):49-55.
- [11]. Musi N, et al. AMP-activated protein kinase activity and glucose uptake in rat skeletal muscle. Am J Physiol Endocrinol Metab. 2001 May;280(5):E677-84.
- [12]. Nakai T, et al. Effects of adenine nucleotide analogues on myocardial dysfunction during reperfusion after ischemia in dogs. Journal of cardiovascular pharmacology. 1996 Aug;28(2):264-70. [Content Brief]
- [13]. Katsuki S, et al. Regulation of adenosine cyclic 3',5'-monophosphate and guanosine cyclic 3',5'-monophosphate levels and contractility in bovine tracheal smooth muscle. Mol Pharmacol. 1977 Mar;13(2):330-41.
