2-Aminopurine

• CAT Number: I020804
• CAS Number: 452-06-2
• Molecular Formula: C5H5N5
• Molecular Weight: 135.13
• Purity: 98%
• Solubility: Soluble in DMSO
• Storage: 2-8°C
• IUPAC Name: 7H-purin-2-amine
• InChI: InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
• InChIKey: MWBWWFOAEOYUST-UHFFFAOYSA-N
• SMILES: C1=C2C(=NC(=N1)N)N=CN2

2-Aminopurine（Cat No.:I020804） is a compound that functions as a specific inhibitor of protein kinase R (PKR), a double-stranded RNA-dependent protein kinase. PKR is an important enzyme involved in cellular responses to viral infections and stress signals. By inhibiting PKR, 2-aminopurine can modulate the activation of PKR and its downstream signaling pathways. This compound has been widely used in research to investigate the role of PKR in various cellular processes and to explore its potential as a therapeutic target in viral infections and related diseases.

Reference

1: Brovarets’ OO, Voiteshenko IS, Hovorun DM. Physico-chemical profiles of the wobble ↔ Watson-Crick G*·2AP(w) ↔ G·2AP(WC) and A·2AP(w) ↔ A*·2AP(WC) tautomerisations: a QM/QTAIM comprehensive survey. Phys Chem Chem Phys. 2017 Dec 20;20(1):623-636. doi: 10.1039/c7cp05139e. PubMed PMID: 29227488.
2: Hu T, Suter SR, Mumbleau MM, Beal PA. TLR8 activation and inhibition by guanosine analogs in RNA: Importance of functional groups and chain length. Bioorg Med Chem. 2018 Jan 1;26(1):77-83. doi: 10.1016/j.bmc.2017.11.020. Epub 2017 Nov 11. PubMed PMID: 29174509; PubMed Central PMCID: PMC5733708.
3: Zargarian L, Ben Imeddourene A, Gavvala K, Barthes NPF, Michel BY, Kenfack CA, Morellet N, René B, Fossé P, Burger A, Mély Y, Mauffret O. Structural and Dynamical Impact of a Universal Fluorescent Nucleoside Analogue Inserted Into a DNA Duplex. J Phys Chem B. 2017 Dec 21;121(50):11249-11261. doi: 10.1021/acs.jpcb.7b08825. Epub 2017 Dec 12. PubMed PMID: 29172512.
4: Li S, Liu C, Gong H, Chen C, Chen X, Cai C. Simple G-quadruplex-based 2-aminopurine fluorescence probe for highly sensitive and amplified detection of microRNA-21. Talanta. 2018 Feb 1;178:974-979. doi: 10.1016/j.talanta.2017.10.023. Epub 2017 Oct 16. PubMed PMID: 29136926.
5: Liu X, Chen Y, Fierke CA. Inner-Sphere Coordination of Divalent Metal Ion with Nucleobase in Catalytic RNA. J Am Chem Soc. 2017 Dec 6;139(48):17457-17463. doi: 10.1021/jacs.7b08755. Epub 2017 Nov 22. PubMed PMID: 29116782.
6: Kuznetsova AA, Iakovlev DA, Misovets IV, Ishchenko AA, Saparbaev MK, Kuznetsov NA, Fedorova OS. Pre-steady-state kinetic analysis of damage recognition by human single-strand selective monofunctional uracil-DNA glycosylase SMUG1. Mol Biosyst. 2017 Nov 21;13(12):2638-2649. doi: 10.1039/c7mb00457e. PubMed PMID: 29051947.
7: Peracchi A, Bonaccio M, Credali A. Local conformational changes in the 8-17 deoxyribozyme core induced by activating and inactivating divalent metal ions. Org Biomol Chem. 2017 Oct 25;15(41):8802-8809. doi: 10.1039/c7ob02001e. PubMed PMID: 29022640.
8: Toh DK, Patil KM, Chen G. Sequence-specific and Selective Recognition of Double-stranded RNAs over Single-stranded RNAs by Chemically Modified Peptide Nucleic Acids. J Vis Exp. 2017 Sep 21;(127). doi: 10.3791/56221. PubMed PMID: 28994801.
9: Liu Y, Shen T, Li J, Gong H, Chen C, Chen X, Cai C. Ratiometric Fluorescence Sensor for the MicroRNA Determination by Catalyzed Hairpin Assembly. ACS Sens. 2017 Oct 27;2(10):1430-1434. doi: 10.1021/acssensors.7b00313. Epub 2017 Oct 9. PubMed PMID: 28936869.
10: Zhou J, Opoku-Temeng C, Sintim HO. Fluorescent 2-Aminopurine c-di-GMP and GpG Analogs as PDE Probes. Methods Mol Biol. 2017;1657:245-261. doi: 10.1007/978-1-4939-7240-1_19. PubMed PMID: 28889299.
11: Zhang Y, Xiang D, Tang B, Zhang CY. Sensitive Detection of Transcription Factor in Nuclear Extracts by Target-Actuated Isothermal Amplification-Mediated Fluorescence Enhancement. Anal Chem. 2017 Oct 3;89(19):10439-10445. doi: 10.1021/acs.analchem.7b02451. Epub 2017 Sep 21. PubMed PMID: 28845979.
12: Liao R, Li S, Wang H, Chen C, Chen X, Cai C. Simultaneous detection of two hepatocellar carcinoma-related microRNAs using a clever single-labeled fluorescent probe. Anal Chim Acta. 2017 Aug 29;983:181-188. doi: 10.1016/j.aca.2017.06.026. Epub 2017 Jun 20. PubMed PMID: 28811025.
13: Zhou W, Ding J, Liu J. Splitting a DNAzyme enables a Na(+)-dependent FRET signal from the embedded aptamer. Org Biomol Chem. 2017 Aug 23;15(33):6959-6966. doi: 10.1039/c7ob01709j. PubMed PMID: 28792040.
14: Buchanan HS, Pauff SM, Kosmidis TD, Taladriz-Sender A, Rutherford OI, Hatit MZC, Fenner S, Watson AJB, Burley GA. Correction to “Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy To Access C6-Heteroaryl 2-Aminopurine Ribonucleosides”. Org Lett. 2017 Aug 18;19(16):4411. doi: 10.1021/acs.orglett.7b02273. Epub 2017 Aug 2. PubMed PMID: 28766342.
15: Bronson E, McClure M, Sohl J, Wiedner E, Cox S, Latimer EM, Pearson VR, Hayward GS, Fuery A, Ling PD. EPIDEMIOLOGIC EVALUATION OF ELEPHANT ENDOTHELIOTROPIC HERPESVIRUS 3B INFECTION IN AN AFRICAN ELEPHANT (LOXODONTA AFRICANA). J Zoo Wildl Med. 2017 Jun;48(2):335-343. doi: 10.1638/2016-0063R.1. PubMed PMID: 28749266.
16: Kamiya Y, Donoshita Y, Kamimoto H, Murayama K, Ariyoshi J, Asanuma H. Introduction of 2,6-Diaminopurines into Serinol Nucleic Acid Improves Anti-miRNA Performance. Chembiochem. 2017 Oct 5;18(19):1917-1922. doi: 10.1002/cbic.201700272. Epub 2017 Aug 22. PubMed PMID: 28748559.
17: Liu C, Lv S, Gong H, Chen C, Chen X, Cai C. 2-aminopurine probe in combination with catalyzed hairpin assembly signal amplification for simple and sensitive detection of microRNA. Talanta. 2017 Nov 1;174:336-340. doi: 10.1016/j.talanta.2017.06.028. Epub 2017 Jun 13. PubMed PMID: 28738589.
18: Badugu R, Mao J, Blair S, Zhang D, Descrovi E, Angelini A, Huo Y, Lakowicz JR. Bloch Surface Wave-Coupled Emission at Ultra-Violet Wavelengths. J Phys Chem C Nanomater Interfaces. 2016 Dec 22;120(50):28727-28734. doi: 10.1021/acs.jpcc.6b08086. Epub 2016 Nov 23. PubMed PMID: 28725334; PubMed Central PMCID: PMC5512112.
19: Smith DA, McKenzie G, Jones AC, Smith T. Analysis of TCSPC data: a comparative evaluation of deterministic and probabilistic approaches. Methods Appl Fluoresc. 2017 Jul 18. doi: 10.1088/2050-6120/aa8055. [Epub ahead of print] PubMed PMID: 28718453.
20: Saran R, Yao L, Hoang P, Liu J. Folding of the silver aptamer in a DNAzyme probed by 2-aminopurine fluorescence. Biochimie. 2017 Jul 12. pii: S0300-9084(17)30172-4. doi: 10.1016/j.biochi.2017.07.001. [Epub ahead of print] PubMed PMID: 28711684.