(S)-(-)-Atenolol
(Synonyms: (S)-(-)-阿替洛尔) 目录号 : GC12463
(S)-(-)-Atenolol是一种强效的β-肾上腺素能受体阻滞剂。(S)-(-)-Atenolol是Atenolol的S(-)对映体，Atenolol的R(+)对映体几乎不具有β受体阻滞剂活性。
Cas No.:93379-54-5
Sample solution is provided at 25 µL, 10mM.
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(S)-(-)-Atenolol is a potent β-adrenergic receptor blocker[1]. (S)-(-)-Atenolol is the S(-) enantiomer of Atenolol, while the R(+) enantiomer of Atenolol has almost no β-receptor blocker activity[2, 3]. (S)-(-)-Atenolol is mainly used to treat hypertension and heart-related chest pain[4].
In vitro, (S)-(-)-Atenolol (0-350μM) treated vascular smooth muscle A7r5 cells for 24h inhibited cell viability in a dose-dependent manner and reduced the levels of calmodulin and annexin A6 in the cells[5]. (S)-(-)-Atenolol (200, 400, 600μM) treated MCF7 cells for 72h significantly inhibited cell migration and reduced the percentage of wound healing (WH) of the cells[6].
In vivo, (S)-(-)-Atenolol (90mg/kg/day) was orally administered to spontaneously hypertensive rats for 8 weeks and was less effective in reducing carotid systolic blood pressure than Carvedilol (30mg/kg/day) or Nebivolol (30mg/kg/day)[7].
References:
[1] Mehvar R, Brocks D R. Stereospecific pharmacokinetics and pharmacodynamics of beta-adrenergic blockers in humans[J]. 2001.
[2] Seebauer C T, Graus M S, Huang L, et al. Non–beta blocker enantiomers of propranolol and atenolol inhibit vasculogenesis in infantile hemangioma[J]. The Journal of Clinical Investigation, 2022, 132(3).
[3] Stoschitzky K, Egginger G, Zernig G, et al. Stereoselective features of (R)‐and (S)‐atenolol: Clinical pharmacological, pharmacokinetic, and radioligand binding studies[J]. Chirality, 1993, 5(1): 15-19.
[4] Heel R C, Brogden R N, Speight T M, et al. Atenolol: a review of its pharmacological properties and therapeutic efficacy in angina pectoris and hypertension[J]. Drugs, 1979, 17: 425-460.
[5] Sui J, Zhang J, Tan T L, et al. Comparative proteomics analysis of vascular smooth muscle cells incubated with S-and R-enantiomers of atenolol using iTRAQ-coupled two-dimensional LC-MS/MS[J]. Molecular & Cellular Proteomics, 2008, 7(6): 1007-1018.
[6] İşeri Ö D, Sahin F I, Terzi Y K, et al. beta-Adrenoreceptor antagonists reduce cancer cell proliferation, invasion, and migration[J]. Pharmaceutical biology, 2014, 52(11): 1374-1381.
[7] Del Mauro J S, Prince P D, Allo M A, et al. Effects of third-generation β-blockers, atenolol or amlodipine on blood pressure variability and target organ damage in spontaneously hypertensive rats[J]. Journal of Hypertension, 2020, 38(3): 536-545.
(S)-(-)-Atenolol是一种强效的β-肾上腺素能受体阻滞剂[1]。(S)-(-)-Atenolol是Atenolol的S(-)对映体，Atenolol的R(+)对映体几乎不具有β受体阻滞剂活性[2, 3]。(S)-(-)-Atenolol主要用于治疗高血压和与心脏相关的胸痛[4]。
在体外，(S)-(-)-Atenolol（0-350μM）处理血管平滑肌A7r5细胞24h，以剂量依赖性方式抑制了细胞活力，降低了细胞中钙调蛋白和膜联蛋白A6的水平[5]。(S)-(-)-Atenolol（200, 400, 600μM）处理MCF7细胞72h，显著抑制了细胞迁移，降低了细胞的伤口愈合百分比（WH）[6]。
在体内，(S)-(-)-Atenolol（90mg/kg/day）通过口服治疗自发性高血压大鼠8周，降低颈动脉收缩压的疗效较低，效果不如卡维地洛（Carvedilol，30mg/kg/day）或奈必洛尔（Nebivolol，30mg/kg/day）[7]。
| Cell experiment [1]: | |
Cell lines | A7r5 cells |
Preparation Method | After reaching 80% confluence the cells were incubated with 0-350μM (R)-(+)-Atenolol and (S)-(-)-Atenolol for 24h, in the absence of serum. The viability was examined by the MTT assay. |
Reaction Conditions | 0-350μM; 24h |
Applications | The two enantiomers of Atenolol was toxic to the cells with a drastic decrease in cell viability for any concentration higher than 50μM. The (R)-(+)-Atenolol was somewhat less toxic than the (S)-(-)-Atenolol. |
| Animal experiment [2]: | |
Animal models | Spontaneously hypertensive rats (SHR) |
Preparation Method | SHR rats received Carvedilol 30mg/kg, Nebivolol 30mg/kg, (S)-(-)-Atenolol 90mg/kg, Amlodipine 10mg/kg or vehicle by oral gavage once a day for 8 weeks. WKY rats administered with vehicle were used as normotensive control group. |
Dosage form | 90mg/kg/day for 8 weeks; p.o. |
Applications | Chronic treatment with Carvedilol or Nebivolol attenuates carotid BP and short-term BPV, and reduces target organ damage in SHR to a greater extent than (S)-(-)-Atenolol. |
References: | |
| Cas No. | 93379-54-5 | SDF | |
| 别名 | (S)-(-)-阿替洛尔 | ||
| 化学名 | (S)-2-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide | ||
| Canonical SMILES | O[C@H](COC1=CC=C(CC(N)=O)C=C1)CNC(C)C | ||
| 分子式 | C14H22N2O3 | 分子量 | 266.34 |
| 溶解度 | Soluble to 25 mM in sterile water | 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 | 3.7546 mL | 18.773 mL | 37.546 mL |
| 5 mM | 0.7509 mL | 3.7546 mL | 7.5092 mL |
| 10 mM | 0.3755 mL | 1.8773 mL | 3.7546 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 |
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| % 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。
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Quality Control & SDS
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- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet