55721-87-4

Basic information

• Product Name: chlorin-e₆ trimethyl ester
• CAS NO: 55721-87-4
• Molecular Weight: 638.764
• Mol File: 55721-87-4.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: chlorin-e₆ trimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: chlorin-e₆ trimethyl ester(55721-87-4)
• EPA Substance Registry System: chlorin-e₆ trimethyl ester(55721-87-4)

Safety Data

• Hazardous Substances Data: 55721-87-4(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 5594-30-9 pheophorbide a methyl ester 
• 15664-29-6 pheophorbide A 
• 74-88-4 methyl iodide 
• 5594-30-9 pheophorbide a methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 107-10-8 propylamine 
• 603-17-8 pheophytin a 
• 15664-29-6 pheophorbide-a 
• 5594-30-9 methylpheophorbide a 
• 124-41-4 sodium methylate 

Downstream Products

• 24533-72-0 pyropheophorbide a 
• 5594-30-9 pheophorbide a methyl ester 

Relevant articles and documents

Antitumor agents. Part 209: Pheophorbide-a derivatives as photo-Independent cytotoxic agents.

A methanolic crude extract of the plant Garuga pinnata Roxb. (Burseraceae) showed promising cytotoxic activity against a panel of human tumor cell lines in vitro, including KB and its drug-resistant sublines (Ferguson et al. Cancer Res. 1988, 48, 5956). Pheophorbide-a and-b methyl esters (3,4) were isolated as active principles with broad photo-dependent cytotoxic activities in the micromolar range. These findings prompted SAR studies of known and novel pheophorbide-a derivatives as photo-dependent and photo-independent cytotoxic agents. The results showed that zinc-protoporphyrin IX (10), zinc 13(R)-hydroxypheophorbide-a methyl ester (22), and zinc chlorin-e6 trimethyl ester (13) possessed photo-independent cytotoxic activity. Compounds 13 and 22 were the most active cytotoxic agents of the series (mean ED(50) 4.6 +/- 1.0 microM and 5.7 +/- 0.7 microM, respectively) against KB cells incubated in the dark.

PHOTOSENSITIZER COMPOUNDS, METHODS OF MANUFACTURE AND APPLICATION TO PLANTS

Provided herein are compounds of general Formula I: or agriculturally acceptable salts thereof. The compounds of Formula I can be used to improve the health of plants. For example, the compounds of Formula I can be used to inhibit a microbial pathogen of a plant, or to increase resistance of a plant to one or more abiotic stress. Methods of manufacturing the compounds of general Formula I, as well as synthetic intermediates are also provided.

S,S-Chiral Linker Induced U Shape with a Syn-facial Sensitizer and Photocleavable Ethene Group

There is a major need for light-activated materials for the release of sensitizers and drugs. Considering the success of chiral columns for the separation of enantiomer drugs, we synthesized an S,S-chiral linker system covalently attached to silica with a sensitizer ethene near the silica surface. First, the silica surface was modified to be aromatic rich, by replacing 70% of the surface groups with (3-phenoxypropyl)silane. We then synthesized a 3-component conjugate [chlorin sensitizer, S,S-chiral cyclohexane and ethene building blocks] in 5 steps with a 13% yield, and covalently bound the conjugate to the (3-phenoxypropyl)silane-coated silica surface.?We hypothesized that the chiral linker would increase exposure of the ethene site for enhanced?1O2-based sensitizer release. However, the chiral linker caused the sensitizer conjugate to adopt a U shape due to favored 1,2-diaxial substituent orientation; resulting in a reduced efficiency of?surface loading.?Further accentuating the?U shape was π–π stacking between the?(3-phenoxypropyl)silane and sensitizer. Semiempirical calculations and?singlet oxygen luminescence?data provided deeper insight into the sensitizer's orientation and release. This study has lead to insight on modifications of surfaces for drug photorelease and can help lead to the development of miniaturized photodynamic devices.