8-Bromoguanosine
(Synonyms: 8-溴鸟苷) 目录号 : GC42623
A brominated derivative of guanosine
Cas No.:4016-63-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
8-Bromoguanosine is a brominated derivative of guanosine. Purine nucleobases with bromine at position eight are known to preferentially adopt the syn conformation as nucleosides and, thus, can be used to reduce the conformational heterogeneity of RNA to potentially enhance its function. It is reported to activate lymphocytes through an intracellular mechanism to exert immunostimulatory effects.
| Cas No. | 4016-63-1 | SDF | |
| 别名 | 8-溴鸟苷 | ||
| Canonical SMILES | O=C1C2=C(N([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C(Br)=N2)N=C(N)N1 | ||
| 分子式 | C10H12BrN5O5 | 分子量 | 362.1 |
| 溶解度 | DMF: 30 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 20 mg/ml | 储存条件 | Store at -20°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.7617 mL | 13.8083 mL | 27.6167 mL |
| 5 mM | 0.5523 mL | 2.7617 mL | 5.5233 mL |
| 10 mM | 0.2762 mL | 1.3808 mL | 2.7617 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Formation of 8-S-L-cysteinylguanosine from 8-Bromoguanosine and cysteine
Bioorg Med Chem Lett 2013 Jul 1;23(13):3864-7.PMID:23714713DOI:10.1016/j.bmcl.2013.04.084.
When 8-Bromoguanosine was incubated with cysteine at pH 7.4 and 37 °C, a previously unidentified product was formed as a major product in addition to guanosine. The product was identified as a cysteine substitution derivative of guanosine at the 8 position, 8-S-L-cysteinylguanosine. The reaction was accelerated under mildly basic conditions. The cysteine adduct of guanosine was fairly stable and decomposed with a half-life of 193 h at pH 7.4 and 37 °C. Similar results were observed for incubation of 8-bromo-2'-deoxyguanosine with cysteine. The results suggest that 8-bromoguanine in nucleosides, nucleotides, RNA, and DNA can react with thiols resulting in stable adducts.
Singlet O2 Reactions with Radical Cations of 8-Bromoguanine and 8-Bromoguanosine: Guided-Ion Beam Mass Spectrometric Measurements and Theoretical Treatments
J Phys Chem A 2022 Jan 13;126(1):68-79.PMID:34941276DOI:10.1021/acs.jpca.1c09552.
8-Bromoguanosine is generated in vivo as a biomarker for early inflammation. Its formation and secondary reactions lead to a variety of biological sequelae at inflammation sites, most of which are mutagenic and linked to cancer. Herein, we report the formation of radical cations of 8-bromoguanine (8BrG•+) and 8-Bromoguanosine (8BrGuo•+) and their reactions toward the lowest excited singlet molecular oxygen (1O2)─a common reactive oxygen species generated in biological systems. This work aims to investigate synergistic, oxidatively generated damage of 8-brominated guanine and guanosine that may occur upon ionizing radiation, one-electron oxidation, and 1O2 oxidation. Capitalizing on measurements of reaction product ions and cross sections of 8BrG•+ and 8BrGuo•+ with 1O2 using guided-ion beam tandem mass spectrometry and augmented by computational modeling of the prototype reaction system, 8BrG•+ + 1O2, using the approximately spin-projected ωB97XD/6-31+G(d,p) density functional theory, the coupled cluster DLPNO-CCSD(T)/aug-cc-pVTZ and the multireference CASPT2(21,15)/6-31G**, probable reaction products, and potential energy surfaces (PESs) were mapped out. 8BrG•+ and 8BrGuo•+ present similar exothermic oxidation products, and their reaction efficiencies with 1O2 increase with decreasing collision energy. Both single- and multireference theories predicted that the two most energetically favorable reaction pathways correspond to 1O2-addition to the C8 and C5-positions of 8BrG•+, respectively. The CASPT2-calculated PES represents the best quantitative agreement with the experimental benchmark, in that the oxidation exothermicity is close to the water hydration energy of product ions and, thus, is able to eliminate a water ligand in the product ions.
Antiparallel RNA G-quadruplex Formed by Human Telomere RNA Containing 8-Bromoguanosine
Sci Rep 2017 Jul 27;7(1):6695.PMID:28751647DOI:10.1038/s41598-017-07050-w.
In this study, by combining nuclear magnetic resonance (NMR), circular dichroism (CD), liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS), and gel electrophoresis, we report an unusual topological structure of the RNA G-quadruplex motif formed by human telomere RNA r(UAGGGU) containing 8-Bromoguanosine. Results showed that the RNA sequence formed an antiparallel tetramolecular G-quadruplex, in which each pair of diagonal strands run in opposite directions. Furthermore, guanosines were observed both in syn- and anti-conformations. In addition, two of these G-quadruplex subunits were found to be stacking on top of each other, forming a dimeric RNA G-quadruplex. Our findings provide a new insight into the behavior of RNA G-quadruplex structures.
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.PMID:10672534DOI:10.1016/s1011-1344(99)00131-1.
New caged derivatives of hydrolysis-resistant 8-bromoadenosine cyclic 3',5'-monophosphate (8-Br-cAMP) and 8-Bromoguanosine cyclic 3',5'-monophosphate (8-Br-cGMP) are described. The compounds are the axial and equatorial isomers of the (7-methoxycoumarin-4-yl)methyl (MCM) esters of cyclic nucleotides. Synthesis is accomplished by treatment of 4-bromomethyl-7-methoxycoumarin with the tetra-n-butylammonium salts of the 8-bromo-substituted cyclic nucleotides or with the free acids of 8-Br-cAMP and 8-Br-cGMP in the presence of silver(I) oxide. MCM-caged 8-Br-cAMP and MCM-caged 8-Br-cGMP liberate 8-Br-cAMP and 8-Br-cGMP during irradiation with ultraviolet light within a few nanoseconds. They show favorable absorption properties and quantum yields and are resistant to hydrolysis in aqueous buffer solutions. The moderate fluorescence properties of the caged compounds in comparison with the strongly fluorescent 4-hydroxymethyl-7-methoxycoumarin (MCM-OH) photoproduct allow the indirect estimation of the amount of photolytically released cyclic nucleotides in aqueous buffer solutions using fluorescence measurements. Their usefulness for physiological studies has been examined in a mammalian cell line expressing the cyclic nucleotide-gated ion channel of bovine olfactory sensory neurons using the patch-clamp technique and confocal laser scanning microscopy. The caged compounds serve as efficient and rapid intracellular sources of 8-Br-cAMP and 8-Br-cGMP. However, at least in HEK 293 cells, fluorescence signals cannot be used to monitor the photolysis of MCM-caged 8-Br-cAMP and 8-Br-cGMP, due to quenching of the fluorescence of MCM-OH.
Regulation of intracellular Ca2+ by 8-Bromoguanosine 3':5'-cyclic monophosphate, felodipine and ryanodine in rat caudal artery
Eur J Pharmacol 1996 Dec 27;318(1):97-100.PMID:9007519DOI:10.1016/s0014-2999(96)00908-9.
45Ca2+ efflux in isolated rat caudal artery was measured in the absence and presence of 8-Bromoguanosine 3':5'-cyclic monophosphate (8-Br-cGMP), felodipine or ryanodine after stimulation of alpha 1-adrenoceptors. The objectives of this study were to identify the mechanisms of action of 8-Br-cGMP, felodipine and ryanodine in a vascular resistance vessel. 8-Br-cGMP and ryanodine but not felodipine increased basal 45Ca2+ efflux. Phenylephrine-induced 45Ca2+ efflux was reduced by all three antagonists. The results of this study demonstrate that, (1) 8-Br-cGMP-mediated relaxation is affected in part by an increased extrusion of intracellular Ca2+ and/or inhibition of intracellular Ca2+ release, (2) the Ca(2+)-channel antagonist, felodipine, impairs intracellular Ca2+ release and (3) ryanodine reduced phenylephrine-induced Ca2+ efflux by depleting intracellular Ca2+ stores.