8-BROMOADENOSINE Chemical Properties

Melting point:

210-212 °C (dec.)(lit.)

Boiling point:

717.7±70.0 °C(Predicted)

Density 

1.8171 (rough estimate)

refractive index 

1.6400 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

pka

12.89±0.70(Predicted)

form 

powder

color 

white

Water Solubility 

Soluble in DMSO, and DMF. Insoluble in water.

Sensitive 

Air Sensitive

BRN 

627737

CAS DataBase Reference

2946-39-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25-22

WGK Germany 

3

F 

10-23

HS Code 

2934 99 90

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

8-BROMOADENOSINE Usage And Synthesis

Description

8-Bromoadenosine is a nucleotide that is structurally related to adenosine. It can be used as an inhibitor of guanine nucleotide-binding proteins and has shown biological properties in vitro. 8-Bromoadenosine has been shown to inhibit the mitochondrial membrane potential, cytosolic Ca2+, and the synthesis of RNA and protein. 8-Bromoadenosine also inhibits leukemia inhibitory factor (LIF) production by 3T3-L1 preadipocytes and induces apoptosis in T84 cells.

Chemical Properties

Off-White Solid

Uses

8-Bromoadenosine is an adenosine binding inhibitor. formation of 8-S-L-cysteinyladenosine from 8-Bromoadenosine and cysteine.

Definition

ChEBI: 8-Bromoadenosine is a purine nucleoside.

Synthesis

The general procedure for the synthesis of (2R,3R,4S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol from (2R,3R,4S,5R)-2-(6-amino-8-bromo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol is as follows: embodiment 1: the modified The synthesis of siRNA molecules involves the preparation of 8-methoxyadenosine phosphoramidite and its incorporation in the antisense chain of cystatinase 2 siRNA. FIG. 7A illustrates the structure of double-stranded positive control siRNAs (SEQ ID NO:20 (upper strand) and SEQ ID NO:21 (lower strand)) versus double-stranded negative control siRNAs (SEQ ID NO:22 (upper strand) and SEQ ID NO:23 (lower strand)). FIG. 7B illustrates a schematic representation of individually modified siRNAs, wherein the modifications include, but are not limited to, 8-malonylideneoxyadenosine, 8-phenylethoxyadenosine, and 8-cyclohexylethoxyadenosine. In FIG. 7B, 4AS corresponds to SEQ ID NO:24, 6AS corresponds to SEQ ID NO:25, 10AS corresponds to SEQ ID NO:26, and 15AS corresponds to SEQ ID NO:27. Bromination reactions of adenosine have been reported in the field of chemistry; typically, yields of 8-bromoadenosine ranging from about 75% to about 82.5% are obtained using a fourfold excess of bromine. During the synthesis of nucleo-phosphoramidites, the 5'-OH of N'-benzoyl adenosine was first protected in order to protect the 2'-OH group. Subsequently, 2'-OH was protected using tert-butyldimethylsilyl chloride (TBDMS-Cl).Although the addition of Ag+ ions helped to reduce the unwanted reaction of 3'-OH, side reactions usually still occurred, leading to a significant decrease in the overall yield. Therefore, in order to increase the overall yield, a novel protecting group, dibutylmethylsilyl disilicate (DTBSDT), was employed, which protects both 5'-OH and 3'-OH and makes 2'-OH easily protected by TBDMS-Cl. The two reactions are essentially one-pot reactions, avoiding cumbersome separation steps. The reaction was nearly quantitative and the product yield was about 96% to 98% (see Figures 3 and 4). In methanol, the methoxy derivatives were synthesized using sodium methanol reagents to give 8-methoxyadenosine derivatives and 8-oxoadenosine derivatives. The isolation of these two derivatives was more complicated and the yield of the desired compounds was less than 50%. Therefore, by reacting n-BuLi with an excess of anhydrous methanol to generate the methoxy anion in situ, the reaction is much more efficient, with yields of about 85% to 93% of the desired product. Deprotection of 5'-OH and 3'-OH was accomplished at subzero temperature using a special fluoride reagent, HF-pyridine. The product yields of these DMT reactions were low, about 40% to 50%. The product yield of the phosphoramidite synthesis step was about 95% to 98%. Subsequently, 8-methoxyadenosine phosphoramidite is doped into positions 9 or 14 of the antisense chain (corresponding to positions 11 and 6 of the sense chain, respectively), or both positions 9 and 14. The propargyl portion of adenosine at position 8 simplifies the synthesis of other 8-substituted adenosine analogs. The propargyl portion of 8-alkynyl adenosine in the siRNA can be reacted with a suitable water-soluble azide via a "click" reaction to form the desired minor groove modification.

References

[1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 9992 - 9997
[2] European Journal of Organic Chemistry, 2009, # 10, p. 1515 - 1521
[3] Patent: WO2011/119674, 2011, A1. Location in patent: Page/Page column 50-51
[4] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17643 - 17652
[5] Synthesis, 2004, # 17, p. 2799 - 2804

8-BROMOADENOSINE(2946-39-6)Related Product Information

• 8-BROMOADENOSINE
• 8-BROMOADENINE
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• 8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, SP-ISOMER SODIUM SALT
• 8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT HYDRATE
• 8-BROMOADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT
• 8-BROMOADENOSINE-2',3,5'-TRIACETATE,2',3',5'-TRI-O-ACETYL-8-BROMOADENOSINE
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• 8-bromoadenosine 5'-triphosphate sodium
• 8-BROMO-CADP-RIBOSE
• 8-bromoadenosine 5'-monophosphate*free acid,8-BROMOADENOSINE 5'-MONOPHOSPHATE
• 8-BROMOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE
• 8-bromoadenosine 5'-triphosphate
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• 8-bromoadenosine 5'-diphosphate
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• 8-bromoadenosine-3',5'-cyclic monophosphorothioate
• BETA-BROMOADENOSINE-5'-TRIPHOSPHATE SODIUM