| Identification | Back Directory | [Name]
Pheophorbide A | [CAS]
15664-29-6 | [Synonyms]
PHEOPHORBIDE A
Phaeophorbide A
Pheophorbide A (>
Chlorophyll Impurity 2
13-Epi-phaeophorbide-a
pheophorbide a AldrichCPR
Demagnesia chloric acid -a
Pheophorbide a (mixture of diastereomers)
[3s-(3alpha,4beta,21beta)]-ramethyl-20-oxo
Pheophorbide A (>80%) (mixture of diastereomers)
3-phorbinepropanoicacid,9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tet
(3S,4S)-9-Ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid
3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-, (3S,4S)-
Rel-3-[(3R,4R)-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinylphorbin-3-yl]propanoic acid
3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-, (3S,4S,21R)-
[3S-(3alpha,4beta,21beta)]-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinylphorbine-3-propionic acid
Inchi=1/C35H36N4o5/C1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/H8,12-14,17,21,31,36,39H,1,9-11H2,2-7H3,(H,40,41)/B22-12-,23-13-,24-12-,25-14-,26-13-,27-14- | [EINECS(EC#)]
239-738-5 | [Molecular Formula]
C35H36N4O5 | [MDL Number]
MFCD00210345 | [MOL File]
15664-29-6.mol | [Molecular Weight]
592.7 |
| Chemical Properties | Back Directory | [Melting point ]
191-195 °C | [Boiling point ]
1019.0±65.0 °C(Predicted) | [density ]
1.282±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [solubility ]
DMSO: soluble0.5mg/mL, clear (warmed) | [form ]
Solid | [color ]
blue, to dark brown to black | [Stability:]
Light Sensitive | [InChIKey]
NSFSLUUZQIAOOX-QEWKCGBTSA-N | [SMILES]
O=C([C@@H]1C(OC)=O)C(C(N/2)=C1C([C@@H](CCC(O)=O)[C@@H]/3C)=NC3=C/4)=C(C)C2=C\C5=N/C(C(C)=C5CC)=C\C6=C(C=C)C(C)=C4N6 | [EPA Substance Registry System]
3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-, (3S,4S,21R)- (15664-29-6) |
| Hazard Information | Back Directory | [Uses]
Pheophorbide a is a chlorophyll-related compound studied for it’s anti-tumor & anti-cancer activity. | [Uses]
Pheophorbide-a has been used as a photosensitizer:
- for the photodynamic therapy (PDT) in oral cancer cell lines
- to test its effect on inducing oxidative stress and death in L. amazonensis
- to test its effect on the viability of HeLa cells
| [Definition]
ChEBI: Pheophorbide a is a pheophorbide. It is a conjugate acid of a pheophorbide a(2-). | [Biochem/physiol Actions]
Pheophorbide-a, due to its photosensitizing effect, may serve as a promising bioactive compound to treat leishmaniasis. It is a metabolite of chlorophyll and possesses immunostimulation functionality. Pheophorbide-a is a photosensitizer for the photodynamic therapy. It is an ATP Binding Cassette Subfamily G Member 2 (ABCG2) transporter specific substrate. Overexpression of ATP-binding cassette (ABC) transporters in cancer cells is associated with the multidrug resistance phenotype. | [Enzyme inhibitor]
This chlorophyll a degradation intermediate (MW = 579.68 g/mol; CAS 15664-29-6), which is identical to chlorophyll a, except for the absence of the latter’s magnesium ion and ester at the 17-position, is obtained by acid hydrolysis of chlorophyll a. Pheophorbide a inhibits acyl-CoA:cholesterol acyltransferase and magnesium protoporphyrin IX methyltransferase, acts as an endothelin receptor antagonist, and also induces apoptosis. Pheophorbide a is also as an anti-tumor promoter. | [in vivo]
Pheophorbide A-mediated photodynamic therapy (Pa-PDT) (10 mg/kg (i.v.) or 30 mg/kg (i.p.)) significantly inhibits tumor growth in C3H mouse model with subcutaneous injection of AT-84 cells[3]. | Animal Model: | Male immunocompetent C3H mouse (six-week-old, inoculated subcutaneously with AT-84 cells)[3] | | Dosage: | 10 mg/kg intravenous (i.v.) or a 30 mg/kg intraperitoneal (i.p.) injection | | Administration: | IV or IP; after 24 h, PDT was performed | | Result: | Pa-PDT, especially i.v. Pa-PDT, significantly inhibited tumor growth up to 70%, while the i.p. Pa-PDT-induced inhibition was up to 43.4% relative to the control group at the end of period. |
|
|
|