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Methyl pyropheophorbide-a

Names

[ CAS No. ]:
6453-67-4

[ Name ]:
Methyl pyropheophorbide-a

[Synonym ]:
3-Phorbinepropanoic acid, 9-ethenyl-14-ethyl-24,25-dihydro-4,8,13,18-tetramethyl-20-oxo-, methyl ester
Methyl pyrophaeophorbide a
9-Ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxophorbine-3-propanoi
Methyl 3-(14-ethyl-4,8,13,18-tetramethyl-20-oxo-9-vinyl-24,25-dihydro-3-phorbinyl)propanoate
MPP A
PYROPHEOPHORBIDE A METHYL ESTER
MFCD00057989
Methyl pyropheophorbide a
Methyl-13-decarboxy-methyl phaeophorbide-a
9-Ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxophorbine-3-propanoicacid meth
Pyropheophorbide-alpha methyl ester
Methyl carbamic pyrophyllate a

Biological Activity

[Description]:

Methyl pyropheophorbide-a (Pyropheophorbide-a methyl ester), a chlorophyll-a derivative, and is a potent photosensitizer that can be used in photodynamic therapy (PDT) of cancer. Methyl pyropheophorbide-a has photodynamic activity and can induce apoptosis and inhibit tumor growth[1][2].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Others >> Others

[In Vitro]

Pyropheophorbide-a methyl ester (2 μM; 12 h) inhibits the cell cycle progression from the G0/G1-phases and induces apoptosis at the light dosage of 55.6 kJ/m2 in PC-3M cells[2]. Pyropheophorbide-a methyl ester (0.2-15 μM; 20 h) has no significant dark cytotoxicity in NCI-h446 cells[1]. Pyropheophorbide-a methyl ester (0.1-15 μM; 20 h) mediates a dose-dependent photocytotoxicity in the NCI-h446 cells[1]. Pyropheophorbide-a methyl ester (2-4 μM; 0-24 h) induces apoptosis of NCI-h446 cells in a time-dependent manner[1]. Pyropheophorbide-a methyl ester (0.5-4 μM; 0-20 h) shows a photocytotoxicity in PC-3M cells[2]. Apoptosis Analysis[1] Cell Line: PC-3M cells Concentration: 2 μM Incubation Time: 12 h Result: Apoptosis rate was about 0.27%, 6.15%, 20.49%, 50.76%, 65.39%, 64.92%, and 64.37% at 1, 3, 6, 12, 18, and 24 h posttreatment, respectively under the conditions of LC75 (2 μM+55.6 kJ/m2).

[In Vivo]

Pyropheophorbide-a methyl ester (15 mg/kg; tail vein and topical injection) inhibits the growth of PC-3M tumors in mice[2]. Animal Model: Male BALB/c nude mice (6-8 weeks, 16-20 g) bearing PC-3M tumor[2] Dosage: 15 mg/kg Administration: Tail vein injection and topical injection Result: The tumor volume and the weight inhibition rate were 46.78%, 41.84% in tail vein injection group and 78.66%, 72.07% in topical injection group, respectively.

[References]

[1]. Sun X, et, al. Photodynamic therapy with pyropheophorbide-a methyl ester in human lung carcinoma cancer cell: efficacy, localization and apoptosis. Photochem Photobiol. 2002 Jun;75(6):644-51.

[2]. Tian Y, et, al. Cell death induced by MPPa-PDT in prostate carcinoma in vitro and in vivo. Biochem Biophys Res Commun. 2006 Sep 22;348(2):413-20.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
924.1±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C34H36N4O3

[ Molecular Weight ]:
548.675

[ Flash Point ]:
512.7±34.3 °C

[ Exact Mass ]:
548.278748

[ PSA ]:
99.67000

[ LogP ]:
6.95

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.642

[ Storage condition ]:
-20°C

MSDS

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Related Compounds