Cyclo(his-pro) (Cyclo(histidyl-proline))
(Synonyms: 环(组氨酰-脯氨酰),Cyclo(histidyl-proline); Histidylproline diketopiperazine) 目录号 : GC30806
A cyclic neuropeptide and metabolite of TRH
Cas No.:53109-32-3
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
Cyclo(L-His-L-Pro) is an endogenous cyclic neuropeptide and a metabolite of thyrotropin-releasing hormone (TRH).1 It is formed in the hypothalamus via the hydrolytic removal of pyroglutamic acid from TRH followed by non-enzymatic cyclization but is also synthesized de novo.2 It is ubiquitously expressed in the CNS, but is also found in the gastrointestinal tract and blood. Cyclo(L-His-L-Pro) (50 ?M) reduces LPS-induced production of reactive oxygen species (ROS) and nitric oxide (NO), as well translocation of NF-κB in BV-2 microglia. Levels of cyclo(L-His-L-Pro) are increased in rat brain after six weeks of continuous ethanol consumption and cyclo(L-His-L-Pro) reduces ethanol-induced sleep time in rats when administered at a dose of 1 ?mol/kg.1,3 Cyclo(L-His-L-Pro) induces analgesia in the hot-plate test and reduces acetic acid-induced writhing in mice, effects that can be partially reversed by the opioid antagonist naloxone.1
1.Prasad, C.Neurobiology of cyclo(His-Pro)Ann. N. Y. Acad. Sci.553(1)232-251(1989) 2.Grottelli, S., Ferrari, I., Pietrini, G., et al.The role of cyclo(His-Pro) in neurodegenerationInt. J. Mol. Sci.17(8)1332(2016) 3.Prasad, C., Matsui, T., and Peterkofsky, A.Antagonism of ethanol narcosis by histidyl-proline diketopiperazineNature268(5616)142-144(1977)
| Cas No. | 53109-32-3 | SDF | |
| 别名 | 环(组氨酰-脯氨酰),Cyclo(histidyl-proline); Histidylproline diketopiperazine | ||
| Canonical SMILES | Cyclo(His-Pro) | ||
| 分子式 | C11H14N4O2 | 分子量 | 234.25 |
| 溶解度 | Water : ≥ 30 mg/mL (128.07 mM) | 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 | 4.2689 mL | 21.3447 mL | 42.6894 mL |
| 5 mM | 0.8538 mL | 4.2689 mL | 8.5379 mL |
| 10 mM | 0.4269 mL | 2.1345 mL | 4.2689 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。
Cyclo(His-Pro) Exerts Protective Carbonyl Quenching Effects through Its Open Histidine Containing Dipeptides
Cyclo(His-Pro) (CHP) is a cyclic dipeptide which is endowed with favorable pharmacokinetic properties combined with a variety of biological activities. CHP is found in a number of protein-rich foods and dietary supplements. While being stable at physiological pH, CHP can open yielding two symmetric dipeptides (His-Pro, Pro-His), the formation of which might be particularly relevant from dietary CHP due to the gastric acidic environment. The antioxidant and protective CHP properties were repeatedly reported although the non-enzymatic mechanisms were scantly investigated. The CHP detoxifying activity towards α,β unsaturated carbonyls was never investigated in detail, although its open dipeptides might be effective as already observed for histidine containing dipeptides. Hence, this study investigated the scavenging properties of TRH, CHP and its open derivatives towards 4-hydroxy-2-nonenal. The obtained results revealed that Pro-His possesses a marked activity and is more reactive than l-carnosine. As investigated by DFT calculations, the enhanced reactivity can be ascribed to the greater electrophilicity of the involved iminium intermediate. These findings emphasize that the primary amine (as seen in l-carnosine) can be replaced by secondary amines with beneficial effects on the quenching mechanisms. Serum stability of the tested peptides was also evaluated, showing that Pro-His is characterized by a greater stability than l-carnosine. Docking simulations suggested that its hydrolysis can be catalyzed by serum carnosinase. Altogether, the reported results evidence that the antioxidant CHP properties can be also due to the detoxifying activity of its open dipeptides, which might be thus responsible for the beneficial effects induced by CHP containing food.
Histidyl-proline diketopiperazine cyclo (His-Pro): identification and characterization in rat pancreatic islets
Measurements of cyclo (His-Pro) in the pancreas were carried out in the rat by a specific radioimmunoassay. Cyclo (His-Pro)-like immunoreactivity was identified in pancreatic islets with a mean concentration of 2023 pg/mg protein, 88-fold higher than that of the whole pancreas. Cyclo (His-Pro) immunoreactivity from pancreatic extracts was indistinguishable immunologically and chromatographically from synthetic cyclo (His-Pro). Insulin-induced hypoglycemia caused a significant, 53% decrease in pancreatic cyclo (His-Pro) concentrations, and FLA-63, a dopamine beta-oxidase inhibitor, also reduced islet cyclo (His-Pro) concentrations 51%. These data indicate that cyclo (His-Pro) is present in rat pancreatic islets and may play a potential role in modulating pancreatic responses to nutrient and pharmacologic stimuli.
Re-evaluation of histidyl-proline diketopiperazine [cyclo(His-Pro)] effects on food intake in the rat
Histidyl-proline diketopiperazine [cyclo(His-Pro)], a metabolite of thyrotropin releasing hormone (TRH), has been reported to decrease food intake of rats in a variety of feeding models following intracerebroventricular (ICV) injection. We have re-evaluated the anorectic effects of cyclo(His-Pro) on food deprivation-induced and spontaneous feeding. When injected ICV at the end of the light period into ad lib fed rats, neither the naturally occurring cyclo(L-His-L-Pro) isomer (14 to 1000 nmole/rat) nor any of the four cyclo(D,L-His-D,L-Pro) stereoisomers (100 nmole/rat) significantly suppressed food intake at any hour for up to 12- or 24-hr post-injection. Bombesin (0.6 nmole/rat ICV) decreased food intake in the same model by up to 86% with anorexia still apparent 15-hr post-injection (71%, p less than 0.001). In two food deprivation-induced feeding models, cyclo(L-His-L-Pro) (100 and 1000 nmole/rat ICV) did not cause anorexia while TRH (10 and 1000 nmole/rat ICV) maximally suppressed food intake by 74% (p less than 0.02) and 50% (p less than 0.01). Occasional transient increases of food consumption were observed in cyclo(His-Pro)-treated rats during both spontaneous and induced feeding. Cyclo(L-His-L-Pro) was also without effect on food intake when intraperitoneally administered at 12.5 and 30 mumole/kg to schedule fed rats. TRH at 30 mumole/kg IP transiently suppressed food intake of schedule fed rats (p less than 0.005). These findings indicate that cyclo(His-Pro) does not exhibit anorectic activity in the rat and cast doubt on the concept that TRH-induced anorexia results from conversion of TRH to an active cyclo(His-Pro) metabolite.
Neurobiology of cyclo(His-Pro)
Evidence for the presence of immunoreactive histidyl-proline diketopiperazine [cyclo (His-Pro)] in the adult human brain
The current study was undertaken to evaluate the presence of cyclo (His-Pro) in adult human brain tissues obtained at autopsy. We found evidence for immunoreactive cyclo (His-Pro), which diluted in parallel to the radioimmunoassay standard curve and which had mobility on HPLC that was similar to synthetic cyclo (His-Pro), in several regions of the adult human brain. Whereas the levels of cyclo (His-Pro) in the pituitary stalk-median eminence were high (2.2 ng/mg protein), the concentrations in the whole hypothalamus were much lower (0.105 ng/mg protein). Among the extrahypothalamic brain regions examined, the levels of cyclo (His-Pro) were highest in the cerebellar hemisphere (0.168 ng/mg protein) and olfactory bulbs (0.180 ng/mg protein) and were lowest in the hippocampus (0.080 ng/mg protein) and occipital cortex (0.079 ng/mg protein). Thus, immunoreactive cyclo (His-Pro) has widespread distribution in the adult human brain and the potential exists for this cyclic diepeptide to play a role in human brain function.