8-BROMOADENOSINE
- Product Name
- 8-BROMOADENOSINE
- CAS No.
- 2946-39-6
- Chemical Name
- 8-BROMOADENOSINE
- Synonyms
- 8-Br-A;8-Br-Ar;NSC 79213;Bromoadenosine;8-Br-Adenosine;8-BROMOADENOSINE;8-BROMO-D-ADENOSINE;Adenosine, 8-bromo-;8-Bromoadenosine,98%;8-BROMOADENOSINE USP/EP/BP
- CBNumber
- CB8695451
- Molecular Formula
- C10H12BrN5O4
- Formula Weight
- 346.14
- MOL File
- 2946-39-6.mol
8-BROMOADENOSINE Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- B6272
- Product name
- 8-Bromoadenosine
- Purity
- powder
- Packaging
- 1g
- Price
- $182
- Updated
- 2021/12/16
- Product number
- B6272
- Product name
- 8-Bromoadenosine
- Purity
- powder
- Packaging
- 5g
- Price
- $646
- Updated
- 2021/12/16
- Product number
- B3795
- Product name
- 8-Bromoadenosine
- Packaging
- 1G
- Price
- $54
- Updated
- 2025/07/31
- Product number
- B3795
- Product name
- 8-Bromoadenosine
- Packaging
- 5G
- Price
- $163
- Updated
- 2025/07/31
- Product number
- 295414
- Product name
- 8-Bromoadenosine
- Packaging
- 1g
- Price
- $315
- Updated
- 2021/12/16
8-BROMOADENOSINE Chemical Properties,Usage,Production
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
58-61-7
2946-39-6
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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 8-BROMOADENOSINE manufacturers
- Product
- 8-BROMOADENOSINE 2946-39-6
- Price
- US $0.00-0.00/G
- Min. Order
- 1G
- Purity
- 97%
- Supply Ability
- 2000
- Release date
- 2025-06-03
- Product
- 8-Bromoadenosine 2946-39-6
- Price
- US $0.00-0.00/KG
- Min. Order
- 100g
- Purity
- 98%min
- Supply Ability
- 200kgs
- Release date
- 2021-09-07
- Product
- 8-BROMOADENOSINE 2946-39-6
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-26