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MedKoo Cat#: 122486 | Name: 8-Bromoadenosine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

8-Bromoadenosine be used as an inhibitor of guanine nucleotide-binding proteins and has shown biological properties in vitro.

Chemical Structure

8-Bromoadenosine
8-Bromoadenosine
CAS#2946-39-6

Theoretical Analysis

MedKoo Cat#: 122486

Name: 8-Bromoadenosine

CAS#: 2946-39-6

Chemical Formula: C10H12BrN5O4

Exact Mass: 345.0073

Molecular Weight: 346.14

Elemental Analysis: C, 34.70; H, 3.49; Br, 23.08; N, 20.23; O, 18.49

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 Weeks
10g USD 550.00 2 Weeks
25g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
8-Bromoadenosine; 2946-39-6; Adenosine, 8-bromo-; 6-Amino-8-bromopurine riboside
IUPAC/Chemical Name
(2R,3R,4S,5R)-2-(6-Amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
InChi Key
VJUPMOPLUQHMLE-UUOKFMHZSA-N
InChi Code
InChI=1S/C10H12BrN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
SMILES Code
O[C@H]1[C@H](N2C(Br)=NC3=C(N)N=CN=C23)O[C@H](CO)[C@H]1O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 346.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Suzuki T, Ogishi A, Shinohara T, Suito S. Formation of 8-S-L- Cysteinyladenosine from 8-Bromoadenosine and Cysteine. Chem Pharm Bull (Tokyo). 2018;66(2):184-187. doi: 10.1248/cpb.c17-00731. PMID: 29386470. 2: Sala L, Lyshchuk H, Šáchová J, Chvátil D, Kočišek J. Different Mechanisms of DNA Radiosensitization by 8-Bromoadenosine and 2'-Deoxy-2'-fluorocytidine Observed on DNA Origami Nanoframe Supports. J Phys Chem Lett. 2022 May 5;13(17):3922-3928. doi: 10.1021/acs.jpclett.2c00584. Epub 2022 Apr 26. PMID: 35472278; PMCID: PMC9083549. 3: Golos TG, Strauss JF 3rd. 8-bromoadenosine cyclic 3',5'-phosphate rapidly increases 3-hydroxy-3-methylglutaryl coenzyme A reductase mRNA in human granulosa cells: role of cellular sterol balance in controlling the response to tropic stimulation. Biochemistry. 1988 May 3;27(9):3503-6. doi: 10.1021/bi00409a056. PMID: 3390448. 4: Cui F, Yan Y, Zhang Q, Yao X, Qu G, Lu Y. Characterization of the interaction between 8-bromoadenosine with human serum albumin and its analytical application. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Nov;74(4):964-71. doi: 10.1016/j.saa.2009.09.001. Epub 2009 Sep 8. PMID: 19775931. 5: Hagen V, Bendig J, Frings S, Wiesner B, Schade B, Helm S, Lorenz D, Kaupp UB. Synthesis, photochemistry and application of (7-methoxycoumarin-4-yl)methyl- caged 8-bromoadenosine cyclic 3',5'-monophosphate and 8-bromoguanosine cyclic 3',5'-monophosphate photolyzed in the nanosecond time region. J Photochem Photobiol B. 1999 Nov-Dec;53(1-3):91-102. doi: 10.1016/s1011-1344(99)00131-1. PMID: 10672534. 6: Martell RE, Ruddon RW. Patterns of human chorionic gonadotropin expression in untreated and 8-bromoadenosine-treated JAR choriocarcinoma cells. Endocrinology. 1990 May;126(5):2757-64. doi: 10.1210/endo-126-5-2757. PMID: 2184024. 7: Iwamoto H. On the ability of 8-bromoadenosine triphosphate to support contractility of vertebrate skeletal muscle fibers. J Muscle Res Cell Motil. 2008;29(1):45-55. doi: 10.1007/s10974-008-9141-1. Epub 2008 Jul 10. PMID: 18615269. 8: Takenaka H, Ikehara M, Tonomura Y. Structure and function of the two heads of the myosin molecule. IV. Physiological functions of various reaction intermediates in myosin adenosinetriphosphatase, studied by the interaction between actomyosin and 8-bromoadenosine triphosphate. J Biochem. 1976 Dec;80(6):1381-92. doi: 10.1093/oxfordjournals.jbchem.a131411. PMID: 138680. 9: Tavale SS, Sobell HM. Crystal and molecular structure of 8-bromoguanosine and 8-bromoadenosine, two purine nucleosides in the syn conformation. J Mol Biol. 1970 Feb 28;48(1):109-23. doi: 10.1016/0022-2836(70)90222-6. PMID: 5448585. 10: Maruyama T, Sato Y, Sakamoto T, Manabe T. Synthesis of the 2'-deoxy-2'-fluoro and 3'-deoxy-3'-fluoro analogues of 8-bromoadenosine. Nucleic Acids Symp Ser. 1997;(37):17-8. PMID: 9585977. 11: Ikehara M, Kaneko M. Studies of nucleosides and nucleotides. XLI. Purine cyclonucleosides. 8. Selective sulfonylation of 8-bromoadenosine derivatives and an alternate synthesis of 8,2'-and 8,3'-S-cyclonucleosides. Tetrahedron. 1970 Sep;26(18):4251-9. doi: 10.1016/s0040-4020(01)93068-6. PMID: 5469477. 12: Murono EP, Washburn AL. Delta 5-3 beta-hydroxysteroid dehydrogenase- isomerase activity in two distinct density Leydig cells from immature rats. Differences in responsiveness to human chorionic gonadotropin or 8-bromoadenosine 3',5'-monophosphate. Biochim Biophys Acta. 1991 Jan 10;1091(1):55-62. doi: 10.1016/0167-4889(91)90222-j. PMID: 1847300. 13: Maus M, Homburger V, Cordier J, Pantaloni C, Bockaert J, Glowinski J, Prémont J. Treatment of intact striatal neurones with cholera toxin or 8-bromoadenosine 3',5'-(cyclic)phosphate decreases the ability of pertussis toxin to ADP-ribosylate the alpha-subunits of inhibitory and other guanine- nucleotide-binding regulatory proteins, Gi and Go. Evidence for two distinct mechanisms. Eur J Biochem. 1991 Mar 14;196(2):313-20. doi: 10.1111/j.1432-1033.1991.tb15819.x. PMID: 1848817. 14: Dib K, el Jamali A, Jacquemin C, Corrèze C. Cyclic AMP regulation of messenger RNA level of the stimulatory GTP-binding protein Gs alpha. Isoproterenol, forskolin and 8-bromoadenosine 3':5'-cyclic monophosphate increase the level of Gs alpha mRNA in cultured astroglial cells. Eur J Biochem. 1994 Jan 15;219(1-2):529-37. doi: 10.1111/j.1432-1033.1994.tb19968.x. PMID: 7508389. 15: Kitagawa Y, Sugimoto E. Interaction between glucocorticoids, 8-bromoadenosine 3',5'-monophosphate, and insulin in regulation of synthesis of carbamoyl-phosphate synthetase I in Reuber hepatoma H-35. Eur J Biochem. 1985 Jul 15;150(2):249-54. doi: 10.1111/j.1432-1033.1985.tb09014.x. PMID: 3894022. 16: Takenaga K. Effects of 8-bromoadenosine 3':5'-cyclic monophosphate on proteolytic enzymes, adhesiveness and lung-colonizing ability of cloned low- metastatic Lewis lung carcinoma cells. Jpn J Cancer Res. 1986 Oct;77(10):998-1004. PMID: 3023266. 17: Wood HN, Braun AC. 8-bromoadenosine 3':5'-cyclic monophosphate as a promoter of cell division in excised tobacco pith parenchyma tissue. Proc Natl Acad Sci U S A. 1973 Feb;70(2):447-50. doi: 10.1073/pnas.70.2.447. PMID: 16592058; PMCID: PMC433279. 18: Ikehara M, Uesugi S. Studies on nucleosides and nucleotides. 38. Synthesis of 8-bromoadenosine nucleotides. Chem Pharm Bull (Tokyo). 1969 Feb;17(2):348-54. doi: 10.1248/cpb.17.348. PMID: 5782965.