pyropheophorbide a
pyropheophorbide a Basic information
- Product Name:
- pyropheophorbide a
- Synonyms:
-
- 3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, (3S,4S)-
- (17S,18S)-3-Vinyl-3-deethyl-17,18-dihydrophytoporphyrin
- 31,32-Didehydrophytochlorin
- 3-Deethyl-3-vinylphytochlorin
- Pyropheophorbide-alpha
- Pyropheophorbide-α
- Magnesium pyrophyllate a
- Chlorophyll Impurity 6
- CAS:
- 24533-72-0
- MF:
- C33H34N4O3
- MW:
- 534.65
- Product Categories:
-
- Porphyrins
- Mol File:
- 24533-72-0.mol
pyropheophorbide a Chemical Properties
- storage temp.
- 4°C, protect from light
- solubility
- DMF: 1 mg/ml; DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
- form
- A crystalline solid
- Boiling point:
- 1006.4±65.0 °C(Predicted)
- Density
- 1.259±0.06 g/cm3(Predicted)
- color
- Brown to black
- InChIKey
- HXQUZGMYNSSKBE-RZSZZPGGSA-N
- SMILES
- C12CC(=O)C3C=1NC(C=3C)C=C1NC(C(C)=C1CC)=CC1NC(=C(C)C=1C=C)C=C1N=C2[C@@H](CCC(O)=O)[C@@H]1C
pyropheophorbide a Usage And Synthesis
Uses
Pyropheophorbide-a (Ppa) is a photosensitizer used in photodynamic therapy (PDT) for tumors. Pyropheophorbide-a exhibits phototoxic effects on tumor cells, such as cervical cancer cells, and also has anti-lipogenesis activity. Pyropheophorbide-a shows potential for research in the fields of cancer and age-related macular degeneration (AMD). Pyropheophorbide-a derivatives also demonstrate inhibitory activity against tumor cells[1][2][3][4].
Definition
ChEBI: Pyropheophorbide a is a pheophorbide. It is a conjugate acid of a pyropheophorbide a anion.
in vivo
Pyropheophorbide-a (1.25 or 2.5 mg/kg, i.v., administration period of 6 hours) exhibits anti-tumor activity in the C57BL/6 mouse model with TC-1 tumor implanted in the peritoneum[4].
| Animal Model: | C57BL/6 mice model |
| Dosage: | 1.25 or 2.5 mg/kg |
| Administration: | intravenous injections (i.v.), 6 h |
| Result: | Resulted in rapid shrinkage of tumors after irradiation. While tumors treated with the same amount of Ppa-only (no irradiation) showed a slow growth |
References
[1] Li W, et al. cRGD Peptide-Conjugated Pyropheophorbide-a Photosensitizers for Tumor Targeting in Photodynamic Therapy. Mol Pharm. 2018 Apr 2;15(4):1505-1514. DOI:10.1021/acs.molpharmaceut.7b01064
[2] Liu YH, et al. Anti-adipogenic activities of pheophorbide a and pyropheophorbide a isolated from wild bitter gourd (Momordica charantia L. var. abbreviata Seringe) in vitro. J Sci Food Agric. 2022 Nov;102(14):6771-6779. DOI:10.1002/jsfa.12044
[3] Bao L L, et al. In vitro and in vivo evaluation of a pyropheophorbide-a derivative as a potential photosensitizer for age-related macular degeneration[J]. Biomedicine & Pharmacotherapy, 2017, 88: 1220-1226.
[4] Chaturvedi P K, et al. Phototoxic effects of pyropheophorbide-a from chlorophyll-a on cervical cancer cells[J]. Journal of Porphyrins and Phthalocyanines, 2014, 18(03): 182-187.
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