2-Selenouracil
目录号 : GC61632
2-Selenouracil是一种有效的用于光动力疗法的光敏剂。
Cas No.:16724-03-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-Selenouracil is a useful specialized photosensitizer for photodynamical therapy[1].
[1]. Mai S, et al. Curious Case of 2-Selenouracil: Efficient Population of Triplet States and Yet Photostable. J Chem Theory Comput. 2019 Jun 11;15(6):3730-3742.
| Cas No. | 16724-03-1 | SDF | |
| Canonical SMILES | O=C(C=CN1)NC1=[Se] | ||
| 分子式 | C4H4N2OSe | 分子量 | 175.05 |
| 溶解度 | DMSO: < 1 mg/mL (ultrasonic;warming;heat to 60°C) (insoluble or slightly soluble) | 储存条件 | Store at -20°C |
| 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 | 5.7127 mL | 28.5633 mL | 57.1265 mL |
| 5 mM | 1.1425 mL | 5.7127 mL | 11.4253 mL |
| 10 mM | 0.5713 mL | 2.8563 mL | 5.7127 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。
Different Oxidation Pathways of 2-Selenouracil and 2-Thiouracil, Natural Components of Transfer RNA
Int J Mol Sci 2020 Aug 19;21(17):5956.PMID:32825053DOI:10.3390/ijms21175956.
Sulfur- and selenium-modified uridines present in the wobble position of transfer RNAs (tRNAs) play an important role in the precise reading of genetic information and tuning of protein biosynthesis in all three domains of life. Both sulfur and selenium chalcogens functionally operate as key elements of biological molecules involved in the protection of cells against oxidative damage. In this work, 2-thiouracil (S2Ura) and 2-Selenouracil (Se2Ura) were treated with hydrogen peroxide at 1:0.5, 1:1, and 1:10 molar ratios and at selected pH values ranging from 5 to 8. It was found that Se2Ura was more prone to oxidation than its sulfur analog, and if reacted with H2O2 at a 1:1 or lower molar ratio, it predominantly produced diselenide Ura-Se-Se-Ura, which spontaneously transformed to a previously unknown Se-containing two-ring compound. Its deselenation furnished the major reaction product, a structure not related to any known biological species. Under the same conditions, only a small amount of S2Ura was oxidized to form Ura-SO2H and uracil (Ura). In contrast, 10-fold excess hydrogen peroxide converted Se2Ura and S2Ura into corresponding Ura-SeOnH and Ura-SOnH intermediates, which decomposed with the release of selenium and sulfur oxide(s) to yield Ura as either a predominant or exclusive product, respectively. Our results confirmed significantly different oxidation pathways of 2-Selenouracil and 2-thiouracil.
Radiation-Induced Oxidation Reactions of 2-Selenouracil in Aqueous Solutions: Comparison with Sulfur Analog of Uracil
Molecules 2021 Dec 27;27(1):133.PMID:35011366DOI:10.3390/molecules27010133.
One-electron oxidation of 2-Selenouracil (2-SeU) by hydroxyl (●OH) and azide (●N3) radicals leads to various primary reactive intermediates. Their optical absorption spectra and kinetic characteristics were studied by pulse radiolysis with UV-vis spectrophotometric and conductivity detection and by the density functional theory (DFT) method. The transient absorption spectra recorded in the reactions of ●OH with 2-SeU are dominated by an absorption band with an λmax = 440 nm, the intensity of which depends on the concentration of 2-SeU and pH. Based on the combination of conductometric and DFT studies, the transient absorption band observed both at low and high concentrations of 2-SeU was assigned to the dimeric 2c-3e Se-Se-bonded radical in neutral form (2●). The dimeric radical (2●) is formed in the reaction of a selenyl-type radical (6●) with 2-SeU, and both radicals are in equilibrium with Keq = 1.3 × 104 M-1 at pH 4 (below the pKa of 2-SeU). Similar equilibrium with Keq = 4.4 × 103 M-1 was determined for pH 10 (above the pKa of 2-SeU), which admittedly involves the same radical (6●) but with a dimeric 2c-3e Se-Se bonded radical in anionic form (2●-). In turn, at the lowest concentration of 2-SeU (0.05 mM) and pH 10, the transient absorption spectrum is dominated by an absorption band with an λmax = 390 nm, which was assigned to the ●OH adduct to the double bond at C5 carbon atom (3●) based on DFT calculations. Similar spectral and kinetic features were also observed during the ●N3-induced oxidation of 2-SeU. In principle, our results mostly revealed similarities in one-electron oxidation pathways of 2-SeU and 2-thiouracil (2-TU). The major difference concerns the stability of dimeric radicals with a 2c-3e chalcogen-chalcogen bond in favor of 2-SeU.
Curious Case of 2-Selenouracil: Efficient Population of Triplet States and Yet Photostable
J Chem Theory Comput 2019 Jun 11;15(6):3730-3742.PMID:31038951DOI:10.1021/acs.jctc.9b00208.
Excited-state MS-CASPT2 and ADC(2) quantum chemical calculations and nonadiabatic dynamics simulations show that 2-Selenouracil is able to both efficiently populate and depopulate reactive triplet states in an ultrashort time scale. Thus, the heavier homologue of 2-thiouracil unites the ultrafast, high-yield intersystem crossing of 2-thiouracil with the short excited-state lifetime and photostability of the parent nucleobase uracil-two properties that have been traditionally thought to be diametrically opposed. Remarkably, while the S2 → S1 → T2 → T1 deactivation dynamics of 2-Selenouracil is analogous to that of 2-thiouracil, the calculations show that the triplet lifetime of 2-Selenouracil should decrease by up to 3 orders of magnitude in comparison to that 2-thiouracil, possibly down to the few-picosecond time scale. The main reasons for this decrease are the lack of a second T1 minimum, the enhanced spin-orbit coupling, and the reduction of the energy barrier to access the T1/ S0 crossing-in particular in aqueous solution-compared to 2-thiouracil. Such unusual photophysical properties, together with its significant red-shifted absorption spectrum, could make 2-Selenouracil a useful specialized photosensitizer for photodynamical therapy.
Gas-Phase Interaction of Calcium (Ca(2+)) with Seleno Derivatives of Uracil
J Chem Theory Comput 2008 Jun;4(6):1002-11.PMID:26621240DOI:10.1021/ct800017j.
The structures and relative stabilities of the complexes between Ca(2+) and 2-Selenouracil, 4-selenouracil, and 2,4-diselenouracil have been investigated through the use of B3LYP/6-311++G(3df,2p)//B3LYP/6-31+G(d,p) density functional theory (DFT) calculations. In those systems where both types of basic centers, a carbonyl or a selenocarbonyl group, are present, Ca(2+) association with the oxygen is favored. For 2,4-diselenouracil the nitrogen atom at position 3 is the most basic site toward Ca(2+) attachment followed by heteroatoms attached to positions 4 and 2. Although the enolic and selenol forms of selenouracils should not be observed in the gas phase, the corresponding Ca(2+) complexes are the most stable ones. More importantly, all the activation barriers associated with the corresponding tautomeric processes are lower than the entrance channel, and therefore not only these complexes should be observed but also they should be the dominant species in the gas phase. Also, Ca(2+) association has a clear catalytic effect on these tautomerization processes, whose activation barriers decrease between 10 and 15 kcal mol(-1).
Selenium substitution effects on excited-state properties and photophysics of uracil: a MS-CASPT2 study
Phys Chem Chem Phys 2020 Jun 7;22(21):12120-12128.PMID:32440669DOI:10.1039/d0cp01369b.
The photophysics of selenium-substituted nucleobases has attracted recent experimental attention because they could serve as potential photosensitizers in photodynamic therapy. Herein, we present a comprehensive MS-CASPT2 study on the spectroscopic and excited-state properties, and photophysics of 2-Selenouracil (2SeU), 4-selenouracil (4SeU), and 2,4-selenouracil (24SeU). Relevant minima, conical intersections, crossing points, and excited-state relaxation paths in the lowest five electronic states (i.e., S0, S1, S2, T2, and T1) are explored. On the basis of these results, their photophysical mechanisms are proposed. Upon photoirradiation to the bright S2 state, 2SeU quickly relaxes to its S2 minimum and then moves in an essentially barrierless way to a nearby S2/S1 conical intersection near which the S1 state is populated. Next, the S1 system arrives at an S1/T2/T1 intersection where a large S1/T1 spin-orbit coupling of 430.8 cm-1 makes the T1 state populated. In this state, a barrier of 6.8 kcal mol-1 will trap 2SeU for a while. In parallel, for 4SeU or 24SeU, the system first relaxes to the S2 minimum and then overcomes a small barrier to approach an S2/S1 conical intersection. Once hopping to the S1 state, there exists an extended region with very close S1, T2, and T1 energies. Similarly, a large S1/T1 spin-orbit coupling of 426.8 cm-1 drives the S1→ T1 intersystem crossing process thereby making the T1 state populated. Similarly, an energy barrier heavily suppresses electronic transition to the S0 state. The present work manifests that different selenium substitutions on uracil can lead to a certain extent of different vertical and adiabatic excitation energies, excited-state properties, and relaxation pathways. These insights could help understand the photophysics of selenium-substituted nucleobases.