HPPH
(Synonyms: 光克洛,Photochlor) 目录号 : GC33100
A photosentizer
Cas No.:149402-51-7
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
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Cell experiment: |
4T1 cells are cultured in 96-well cell culture plates at 1×104/well for 24 h and then treated with GO-PEG-HPPH, HPPH, or GO-PEG at a series of concentrations (0.078125, 0.15625, 0.3125, 0.625, 1.25, 2.5, 5, 10, and 20 μM). Then, 20 µL of MTT solution (5.0 mg/mL) is added to each well. After the 4 h incubation with the MTT, the media are removed and 100 µL of DMSO is added to solubilize the formazan crystals. The cell toxicity efficacy is measured with a microplate reader at an absorbance of 570 nm[1]. |
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Animal experiment: |
Mice[2]Tumor-bearing mice are injected in the tail vein with 0.4 μmol/kg HPPH or 5 mg/kg Porfimer sodium (PII), followed 18-24 h later by illumination to a total light dose of 48 J/cm2 or 132 J/cm2 delivered at a light dose-rate of 14 mW/cm2. Control mice are treated with photosensitizer or light alone. Mice receiving a combination PDT regimen are treated initially with 0.4 μmol/kg HPPH or 5 mg/kg PII followed 18-24 h later by light dose of 48 J/cm2 given at 14 mW/cm2; 9 days later, mice are again injected with photosensitizer and tumors are illuminated with light at a dose of 132 J/cm2 given at 14 mW/cm2[2]. |
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References: [1]. Rong P, et al. Photosensitizer loaded nano-graphene for multimodality imaging guided tumor photodynamic therapy. Theranostics. 2014 Jan 15;4(3):229-39. |
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HPPH is a chlorin that acts as a photosensitizer in photodynamic therapy (PDT) when stimulated with light at 655 nm.1 When administered systemically, HPPH accumulates in tumor cells and, when stimulated with light in the presence of oxygen, reactive oxygen species (ROS) are generated, leading to necrosis within the tumor. HPPH, at a dose of 0.5 mg/kg, increases survival in a nude rat model of glioma.2 It works synergistically with gemcitabine in several pancreatic cancer cell lines to induce cell death.3
1.Dennis, E.J., Dolmans, G.J., Fukumura, D., et al.Photodynamic therapy for cancerNature31-8(2003) 2.Lobel, J., MacDonald, I.J., Ciesielski, M.J., et al.2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a (HPPH) in a nude rat glioma model: implications for photodynamic therapyLasers Surg. Med.29(5)397-405(2001) 3.Sun, G., Anderson, M.A., Gorospe, E.C., et al.Synergistic effects of photodynamic therapy with HPPH and gemcitabine in pancreatic cancer cell linesLasers Surg. Med.44(9)755-761(2012)
| Cas No. | 149402-51-7 | SDF | |
| 别名 | 光克洛,Photochlor | ||
| Canonical SMILES | OC(CC[C@@H]([C@@H]1C)/C2=C(C3)/C4=C(C(C)=C(/C=C5C(CC)=C(C)C(/C=C6N/C(C(C)=C\6C(C)OCCCCCC)=C\C1=N2)=N/5)N4)C3=O)=O | ||
| 分子式 | C39H48N4O4 | 分子量 | 636.82 |
| 溶解度 | DMSO: 125 mg/mL (196.29 mM); Water: < 0.1 mg/mL (insoluble) | 储存条件 | 4°C, away from moisture and 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 | 1.5703 mL | 7.8515 mL | 15.703 mL |
| 5 mM | 0.3141 mL | 1.5703 mL | 3.1406 mL |
| 10 mM | 0.157 mL | 0.7852 mL | 1.5703 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。
Mesoscopic fluorescence tomography of a photosensitizer (HPPH) 3D biodistribution in skin cancer
Acad Radiol 2014 Feb;21(2):271-80.PMID:24439340DOI:10.1016/j.acra.2013.11.009.
Rationale and objectives: Photodynamic therapy (PDT) is a promising strategy for treating cancer. PDT involves three components: a photosensitizer (PS) drug, a specific wavelength of drug-activating light, and oxygen. A challenge in PDT is the unknown biodistribution of the PS in the target tissue. In this preliminary study, we report the development of a new approach to image in three dimensions the PS biodistribution in a noninvasive and fast manner. Materials and methods: A mesoscopic fluorescence tomography imaging platform was used to image noninvasively the biodistribution of 2-[1-hexyloxyethyl]-2 devinyl pyropheophorbide-a (HPPH) in preclinical skin cancer models. Seven tumors were imaged and optical reconstructions were compared to nonconcurrent ultrasound data. Results: Successful imaging of the HPPH biodistribution was achieved on seven skin cancer tumors in preclinical models with a typical acquisition time of 1 minute. Two-dimensional fluorescence signals and estimated three-dimensional PS distributions were located within the lesions. However, HPPH distribution was highly heterogeneous with the tumors. Moreover, HPPH distribution volume and tumor volume as estimated by ultrasound did not match. Conclusions: The results of this proof-of-concept study demonstrate the potential of MFMT to image rapidly the HPPH three-dimensional biodistribution in skin cancers. In addition, these preliminary data indicate that the PS biodistribution in skin cancer tumors is heterogeneous and does not match anatomical data. Mesoscopic fluorescence molecular tomography, by imaging fluorescence signals over large areas with high spatial sampling and at fast acquisition speeds, may be a new imaging modality of choice for planning and optimizing of PDT treatment.
Tumor-Avid 3-(1'-Hexyloxy)ethyl-3-devinylpyrpyropheophorbide-a (HPPH)-3Gd(III)tetraxetan (DOTA) Conjugate Defines Primary Tumors and Metastases
J Med Chem 2022 Jul 14;65(13):9267-9280.PMID:35763292DOI:10.1021/acs.jmedchem.2c00547.
3-(1'-Hexyloxyethyl)-3-devinylpyropheophorbide-a (HPPH or Photochlor), a tumor-avid chlorophyll a derivative currently undergoing human clinical trials, was conjugated with mono-, di-, and tri-Gd(III)tetraxetan (DOTA) moieties. The T1/T2 relaxivity and in vitro PDT efficacy of these conjugates were determined. The tumor specificity of the most promising conjugate was also investigated at various time points in mice and rats bearing colon tumors, as well as rabbits bearing widespread metastases from VX2 systemic arterial disseminated metastases. All the conjugates showed significant T1 and T2 relaxivities. However, the conjugate containing 3-Gd(III)-aminoethylamido-DOTA at position 17 of HPPH demonstrated great potential for tumor imaging by both MR and fluorescence while maintaining its PDT efficacy. At an MR imaging dose (10 μmol/kg), HPPH-3Gd(III)DOTA did not cause any significant organ toxicity in mice, indicating its potential as a cancer imaging (MR and fluorescence) agent with an option to treat cancer by photodynamic therapy (PDT).
Spectroscopic Identification of Diphosphene HPPH and Isomeric Diphosphinyldene PPH2
Angew Chem Int Ed Engl 2023 Mar 1;62(10):e202217353.PMID:36637338DOI:10.1002/anie.202217353.
The simplest diphosphene HPPH and isomeric diphosphinyldene PPH2 features prototype phosphorus-phosphorus multiple bonding properties that have been of long-standing interest in main-group chemistry. Herein, we report the observation of cis-HPPH, trans-HPPH, and PPH2 among the respective laser photolysis products of phosphine (PH3 ) and diphosphine (P2 H4 ) in solid N2 - and Ar-matrices at 10 K. The identification of these P2 H2 isomers with matrix-isolation IR and UV/Vis spectroscopy is supported by D-isotope labeling and the quantum chemical calculations at the CCSD(T)-F12a/cc-pVTZ-F12 level using configuration-selective vibrational configuration interaction theory (VCI). Bonding analyses suggest that the two conformers of HPPH contain standard PP double bonds, whereas, PPH2 resembles P2 in having partial PP triple bond due to the H2 P←P π bonding interaction.
Pluronic F-127: An Efficient Delivery Vehicle for 3-(1'-hexyloxy)ethyl-3-devinylpyropheophorbide-a (HPPH or Photochlor)
Photochem Photobiol 2020 May;96(3):625-635.PMID:31738460DOI:10.1111/php.13183.
To determine the impact of delivery vehicles in photosensitizing efficacy of HPPH, a hydrophobic photosensitizer was dissolved in various formulations: 1% Tween 80/5% dextrose, Pluronic P-123 and Pluronic F-127 in 0.5%, 1% and 2% phosphate buffer solutions (PBS). HPPH was also conjugated to Pluronic F-127, and the resulting conjugate (PL-20) was formulated in PBS. Among the different delivery vehicles, only Pluronic P-123 displayed significant vehicle cytotoxicity, whereas Pluronic F127 was nontoxic. Compared to PL-20, HPPH formulated in Tween80 and Pluronic F-127 showed higher cell-uptake, but lower long-term retention in Colon26 cell compared to PL-20. The higher retention of PL-20 was similarly observed during in vivo uptake with BALB/c mice baring Ct26 tumors. In contrast to the in vitro uptake experiments, PL-20 showed slightly higher uptake compared to HPPH formulated in Tween or Pluronic-F127. A significant difference in pharmacokinetic profile was also observed between the HPPH-Pluronic formulation and PL-20. Under similar in vivo treatment parameters (drug dose 0.47 µmol kg-1 , light dose: 135 J cm-2 at 24 h post-injection of PS), HPPH formulated either in Tween or Pluronic F-127 formulation showed similar in vivo PDT efficacy (20-30% tumor cure on day 60), whereas PL-20 showed 40% tumor cure (day 60).
Photodynamic therapy (PDT) using HPPH for the treatment of precancerous lesions associated with Barrett's esophagus
Lasers Surg Med 2011 Sep;43(7):705-12.PMID:22057498DOI:10.1002/lsm.21112.
Background and objectives: Photodynamic therapy (PDT) with porfimer sodium, FDA approved to treat premalignant lesions in Barrett's esophagus, causes photosensitivity for 6-8 weeks. HPPH (2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a) shows minimal photosensitization of short duration and promising efficacy in preclinical studies. Here we explore toxicity and optimal drug and light dose with endoscopic HPPH-PDT. We also want to know the efficacy of one time treatment with HPPH-PDT. Study design/materials and methods: Two nonrandomized dose escalation studies were performed (18 patients each) with biopsy-proven high grade dysplasia or early intramucosal adenocarcinoma of esophagus. HPPH doses ranged from 3 to 6 mg/m2 . At 24 or 48 hours after HPPH administration the lesions received one endoscopic exposure to 150, 175, or 200 J/cm of 665 nm light. Results: Most patients experienced mild to moderate chest pain requiring symptomatic treatment only. Six patients experienced grade 3 and 4 adverse events (16.6%). Three esophageal strictures were treated with dilatation. No clear pattern of dose dependence of toxicities emerged. In the drug dose ranging study (light dose of 150 J/cm at 48 hours), 3 and 4 mg/m2 of HPPH emerged as most effective. In the light dose ranging study (3 or 4 mg/m2 HPPH, light at 24 hours), complete response rates (disappearance of high grade dysplasia and early carcinoma) of 72% were achieved at 1 year, with all patients treated with 3 mg/m2 HPPH plus 175 J/cm and 4 mg/m2 HPPH plus 150 J/cm showing complete responses at 1 year. Conclusions: HPPH-PDT for precancerous lesions in Barrett's esophagus appears to be safe and showing promising efficacy. Further clinical studies are required to establish the use of HPPH-PDT.