Protohypericin
(Synonyms: 原金丝桃素) 目录号 : GC39064
Protohypericin 是从 Hypericum perforatum 中提取的天然石脑粉。放射性碘化 Protohypericin 能用于肿瘤坏死靶向放射治疗。
Cas No.:548-03-8
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
Protohypericin is a naturally occurring naphthodianthrone derived from plant Hypericum perforatum. Radioiodinated protohypericin is used in Tumor necrosis targeted radiotherapy[1][2].
[1]. Baugh SF. Simultaneous determination of protopseudohypericin, pseudohypericin, protohypericin, and hypericin without light exposure. J AOAC Int. 2005 Nov-Dec;88(6):1607-12. [2]. Liu X, et al. Tumor necrosis targeted radiotherapy of non-small cell lung cancer using radioiodinated protohypericin in a mouse model. Oncotarget. 2015 Sep 22;6(28):26400-10.
| Cas No. | 548-03-8 | SDF | |
| 别名 | 原金丝桃素 | ||
| Canonical SMILES | O=C(C1=C(O)C=C(C)C=C1C2=C34)C3=C(O)C=C(O)C4=C5C(O)=CC(O)=C6C(C7=C(O)C=C(C)C=C7C2=C65)=O | ||
| 分子式 | C30H18O8 | 分子量 | 506.46 |
| 溶解度 | Soluble in DMSO | 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 | 1.9745 mL | 9.8724 mL | 19.7449 mL |
| 5 mM | 0.3949 mL | 1.9745 mL | 3.949 mL |
| 10 mM | 0.1974 mL | 0.9872 mL | 1.9745 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。
From Protohypericin to Hypericin: Photoconversion Analysis Using a Time-Resolved Thermal Lens Technique
Appl Spectrosc 2019 Aug;73(8):936-944.PMID:31149836DOI:10.1177/0003702819846921.
Hypericin (Hyp) is a natural compound with interesting photophysical and pharmacological properties, which has been used in photodynamic therapy and photodynamic inactivation of microorganisms. Its synthesis is based on a series of chemical processes that ends with a light-drug interaction by the photoconversion of Protohypericin (pHyp) to Hyp. Although this photosensitizer is used in a variety of medical applications, the photophysical and photochemical mechanisms involved in the final step related to the photo production of Hyp are not completely understood at the molecular level. Protohypericin concentration, solvents, light irradiation under different wavelengths, and a sort of variables could play an important role in predicting the yielding of this photoconversion process. Here, we used the high-sensitive and remote measurement characteristics of the time-resolved thermal lens technique to investigate the relation between the light-induced photoconversion rate of pHyp to Hyp and the initial concentration pHyp. The results show a linear dependence of the photoreaction rate with the concentration of pHyp, indicating that the overall reaction process includes steps comprising the formation of distinct intermediate species. We demonstrate the applicability of the thermal lens technique for the photochemical characterization of photosensitive drugs at low concentration levels.
Radiopharmaceutical evaluation of (131)I-protohypericin as a necrosis avid compound
J Drug Target 2015 Jun;23(5):417-26.PMID:25655506DOI:10.3109/1061186X.2014.1002787.
Hypericin is a necrosis avid agent useful for nuclear imaging and tumor therapy. Protohypericin, with a similar structure to hypericin except poorer planarity, is the precursor of hypericin. In this study, we aimed to investigate the impact of this structural difference on self-assembly, and evaluate the necrosis affinity and metabolism in the rat model of reperfused hepatic infarction. Protohypericin appeared less aggregative in solution compared with hypericin by fluorescence analysis. Biodistribution data of (131)I-protohypericin showed the percentage of injected dose per gram of tissues (%ID/g) increased with time and reached to the maximum of 7.03 at 24 h in necrotic liver by gamma counting. The maximum ratio of target/non-target tissues was 11.7-fold in necrotic liver at 72 h. Pharmacokinetic parameters revealed that the half-life of (131)I-protohypericin was 14.9 h, enabling a long blood circulation and constant retention in necrotic regions. SPECT-CT, autoradiography, and histological staining showed high uptake of (131)I-protohypericin in necrotic tissues. These results suggest that (131)I-protohypericin is a promising necrosis avid compound with a weaker aggregation tendency compared with hypericin and it may have a broad application in imaging and oncotherapy.
Photocytotoxicity of Protohypericin after photoconversion to hypericin
Planta Med 1999 Dec;65(8):719-22.PMID:10630113DOI:10.1055/s-1999-14050.
In the present study, Protohypericin was synthesised in order to compare its intrinsic photocytotoxicity with that of hypericin. The experimental work was performed in specific filtered light conditions that prevented both an unintended photoconversion of Protohypericin and photosensitization of the cells. Assessing the photocytotoxicity as a function of irradiation time, it was found that the photocytotoxicity of both compounds converged after a long irradiation time (i.e., 15 min), while the difference between the photocytotoxicities was maximal after a short irradiation time (i.e., 1 min). Since this could not be accounted for by a redistribution of Protohypericin during irradiation, and the different irradiation times corresponded to different degrees of photoconversion of Protohypericin into hypericin, the results clearly suggest that Protohypericin exhibits intrinsically a dramatically lower photoactivity as compared to hypericin.
In vitro transport and uptake of Protohypericin and hypericin in the Caco-2 model
Int J Pharm 1999 Oct 15;188(1):81-6.PMID:10528085DOI:10.1016/s0378-5173(99)00203-3.
The intestinal absorption characteristics of Protohypericin, a protonaphthodianthrone present in Hypericum extract, were studied and compared with those of hypericin. The Caco-2 model was used as a model of the intestinal mucosa to assess transepithelial transport and cell uptake. The experimental work was performed in specific light conditions that prevented both the photoconversion of Protohypericin into hypericin and the photosensitization of the cells. Following application of the individual compounds (80-200 microM) to the apical side of the monolayers, the appearance in the basolateral compartment was found to be very low (<0.5%/5 h), but was comparable for both compounds. A lag-time of 2-3 h was observed, suggesting gradual saturation of binding sites on the membrane or inside the cells. Uptake experiments of Protohypericin and hypericin by Caco-2 cells revealed a very significant cellular accumulation (4-8%); uptake was characterised by saturation after 3 h. The findings of this study suggest that Protohypericin has comparable absorption characteristics as hypericin and may contribute to the beneficial effect of Hypericum extract after oral dosing.
Simultaneous determination of protopseudohypericin, pseudohypericin, Protohypericin, and hypericin without light exposure
J AOAC Int 2005 Nov-Dec;88(6):1607-12.PMID:16526439doi
St. John's wort products are commonly standardized to total naphthodianthrones and hyperforin. Determination of these marker compounds is complicated because of the photochemistry of the naphthodianthrones pseudohypericin and hypericin and the instability of hyperforin in solution. Protopseudohypericin and Protohypericin have been identified as naturally occurring naphthodianthrones and, when exposed to light, they are converted into pseudohypericin and hypericin, respectively. However, exposure to light and the resulting naphthodianthrone free-radical reactions oxidize hyperforin. A mathematical relationship between the response of the proto compound and the resulting naphthodianthrone can be established by comparing the analytical response of the proto compound in a solution protected from light with the increase in the analytical response of naphthodianthrone in the same solution after exposure to light. By mathematically converting the proto compounds to their respective products, exposure to light can be avoided while still including proto compounds in a single assay. The method presented here details the reporting of all significant naphthodianthrones, including protopseudohypericin and Protohypericin, without exposure to light. This approach includes the benefits of improved naphthodianthrone precision and protection of hyperforin from oxidation.