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

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

MedKoo CAT#: 122486

CAS#: 2946-39-6

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

Chemical Structure

8-Bromoadenosine

CAS# 2946-39-6

Instruction

Theoretical Analysis

MedKoo Cat#: 122486
Name: 8-Bromoadenosine
CAS#: 2946-39-6
Chemical Formula: C10H12BrN5O4
Exact Mass: 345.01
Molecular Weight: 346.140
Elemental Analysis: C, 34.70; H, 3.49; Br, 23.08; N, 20.23; O, 18.49

Price and Availability

Size	Price	Availability
5g	USD 450	2 Weeks
10g	USD 750	2 Weeks
25g	USD 1250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Suzuki T, Ogishi A, Shinohara T, Suito S. Formation of 8-S-L-
Cysteinyladenosine from 8-Bromoadenosine and Cysteine. Chem Pharm Bull (Tokyo).
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2: Sala L, Lyshchuk H, Šáchová J, Chvátil D, Kočišek J. Different Mechanisms of
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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
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10.1021/bi00409a056. PMID: 3390448.

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Synthesis, photochemistry and application of (7-methoxycoumarin-4-yl)methyl-
caged 8-bromoadenosine cyclic 3',5'-monophosphate and 8-bromoguanosine cyclic
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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
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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
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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-
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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
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PMC433279.

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of 8-bromoadenosine nucleotides. Chem Pharm Bull (Tokyo). 1969 Feb;17(2):348-54.
doi: 10.1248/cpb.17.348. PMID: 5782965.

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