SML1218

Pheophorbide-a

≥90% (HPLC)

• Synonym(s): pheophorbide a, (3S,4S,21R)-9-Ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid, Deacetyl-2-vinylbacteriopheophorbide, Pheophorbide a5
• Empirical Formula (Hill Notation): C₃₅H₃₆N₄O₅
• CAS Number: 15664-29-6
• Molecular Weight: 592.68
• MDL number: MFCD00210345
• UNSPSC Code: 12161501
• PubChem Substance ID: 329825726

Properties

• Assay: ≥90% (HPLC)
• form: powder
• storage condition: protect from light
• color: blue, to dark brown to black
• solubility: DMSO: 0.5 mg/mL, clear (warmed)
• storage temp.: −20°C
• SMILES string: 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
• InChI: 1S/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-,32-30-/t17-,21-,31+/m0/s1
• InChI key: NSFSLUUZQIAOOX-QEWKCGBTSA-N

Description

Application

Pheophorbide-a has been used as a photosensitizer:

• for the photodynamic therapy (PDT) in oral cancer cell lines[1]
• to test its effect on inducing oxidative stress and death in L. amazonensis[2]
• to test its effect on the viability of HeLa cells[3]

Biochem/physiol Actions

Pheophorbide-a, due to its photosensitizing effect, may serve as a promising bioactive compound to treat leishmaniasis.[2] It is a metabolite of chlorophyll and possesses immunostimulation functionality.[3] 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.

Other Notes

light sensitive

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable