PHEOPHORBIDE A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H36N4O5
Molecular Weight	592.6841
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C(C)C2=CC3=C(C=C)C(C)=C(N3)C=C4N=C([C@@H](CCC(O)=O)[C@@H]4C)C5=C6NC(=CC1=N2)C(C)=C6C(=O)[C@@H]5C(=O)OC

InChI

InChIKey=NSFSLUUZQIAOOX-QEWKCGBTSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22790503 | https://www.ncbi.nlm.nih.gov/pubmed/19252412 | https://www.ncbi.nlm.nih.gov/pubmed/19421008

Pheophorbide A is a product of chlorophyll breakdown in plants. It is an active component of the Chinese medicinal herb Scutellaria barbata. Others report on extraction of the drug from sources as varied as spinach leaves and silkworm excreta, and on its confounding appearance in the digestive tracts of animals fed chlorophyll-containing food. Pheophorbide A acts as a photosensitizer in photodynamic therapy. Photoactivated pheophorbide A induces lipid peroxidation, arrests cell growth by activating apoptosis and/or necrosis. In vitro and animal studies have suggested some efficacy for pheophorbide A-mediated photodynamic therapy of cancers.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16450292 \| https://www.ncbi.nlm.nih.gov/pubmed/19276676	Activator 1430
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19421008	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27840908 https://www.ncbi.nlm.nih.gov/pubmed/16450292 https://www.ncbi.nlm.nih.gov/pubmed/19276676	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea.	2003 Feb	12608862
Pheophorbide a as a photosensitizer in photodynamic therapy: in vivo considerations.	2009 Mar 15	19252412
The chlorophyll catabolite pheophorbide a as a photosensitizer for the photodynamic therapy.	2012	22214455
Update on the biochemistry of chlorophyll breakdown.	2013 Aug	22790503

Patents

Sample Use Guides

In Vivo Use Guide

HT29 tumor-bearing nude mice: 30 mg/kg i.p. Azaserine-treated rats: 9 mg/kg i.v.

Route of Administration: Other

In Vitro Use Guide

DNA fragmentation, sub-G1 cell cycle arrest, as well as suppression of the anti-apoptotic protein Bcl-2, release of cytochrome c to the cytosol, and activation of pro-caspase 3 and pro-caspase 9 were observed when Hep3B cells were treated with 40 microg/mL (i. e., 67.5 microM) pheophorbide a for 48 hours.

Name

Type

Language

PHEOPHORBIDE A

Common Name

English

(3S,4S)-9-ETHENYL-14-ETHYL-21-(METHOXYCARBONYL)-4,8,13,18-TETRAMETHYL-20-OXO-3-PHORBINEPROPANOIC ACID

Systematic Name

English

Code System Code Type Description

MESH

C032623