55721-87-4

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as preparation method and application

The invention provides a chlorin e6 ferrocene conjugate with photo- and acoustic-sensitive activity as well as a preparation method and application thereof, and belongs to the technical field of chemical medicines. The chlorin e6 ferrocene conjugate disclosed by the invention has different degrees of inhibition effects on Hela cells in in-vitro anti-tumor activity evaluation. The introduction of the ferrocene group significantly improves the proliferation inhibition activity of the compound on tumor cells, and the proliferation inhibition activity of the chlorin e6 ferrocene conjugate on tumorcells is much higher than that of chlorin e6 used as a control group. The method can be used for preparing photosensitizers and sonosensitizers in photodynamic therapy and sonodynamic therapy methodsfor tumor therapy.

Functionalization of chlorin e6 trimethylester towards potential amphiphilic photosensitizers for photodynamic therapy

Chlorins (dihydroporphyrins) are considered, due to their ideal photophysical properties, as attractive photosensitizers for photodynamic therapy (PDT) of cancer and other therapeutic and diagnostic applications. Chlorophyll a, as a naturally occurring chlorin, forms an almost unlimited renewable resource for preparation of potential biologically active chlorin photosensitizers and fluorescence markers. To achieve amphiphilic photosensitizers which might be selectively enriched in tumor cells, we addressed linkage of per se lipophilic chlorophyll derivatives with carbohydrate based hydrophilic aminopolyols.

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.

Chlorin e6 131:152-anhydride: A key intermediate in conjugation reactions of chlorin e6

Since the patent for the photodynamic therapy agent Talaporfin (mono-L-aspartylchlorin e6) was issued in 1987, confusion has existed regarding which of the three carboxylic acid groups in the chlorophyll degradation product, chlorin e6/su

Syntheses and cellular investigations of 173-, 152-, and 131-amino acid derivatives of chlorin e6

A series of amino acid conjugates of chlorin e6, containing lysine or aspartic acid residues in positions 173, 152, or 131 of the macrocycle were synthesized and investigated as photosensitizers for photodynamic therapy of tumors. All three regioisomers were synthesized in good yields and in five steps or less from pheophytin a (1). In vitro investigations using human carcinoma HEp2 cells show that the 15 2-lysyl regioisomers accumulate the most within cells, and the most phototoxic are the 131 regioisomers. The main determinant of biological efficacy appears to be the conjugation site, probably because of molecular conformation. Molecular modeling investigations reveal that the 173-substituted chlorin e6 conjugates are L-shaped, the 152 and 131 regioisomers assume extended conformations, and the 131 derivatives are nearly linear. It is hypothesized that the 131-aspartylchlorin e6 conjugate may be a more efficient photosensitizer for PDT than the commercial currently used 15 2 derivative.

Design, synthesis, and in vitro photodynamic activities of benzochloroporphyrin derivatives as tumor photosensitizers

Novel benzochloroporphyrin derivatives (BCPDs) were designed, synthesized, and characterized. In vitro dark cytotoxicity and photodynamic efficacy of BCPDs were evaluated by MTT assay on human hepatoma BEL-7402 cells. The experimental results showed that BCPDs 15, 16, 17, and 18 have strong long wavelength absorptions around 670 nm and exhibit significantly lower dark cytotoxicity than BPDMA and possess potent photocytotoxicity, IC50 values 1.32 μg/mL for 15, 0.26 μg/mL for 16, 0.47 μg/mL for 17 of 0.27 μg/mL for 18, and 0.23 μg/mL for BPDMA. Among them, BCPDs 16 and 18 are more effective and promising PDT photosensitizers based on the studies with BEL-7402 cells and show nearly the same photodynamic efficacy as BPDMA. MG-P staining qualitative analysis also indicated that PDT with BCPDs 16 can induce apoptosis in BEL7402 cells.

Mono-(L)-aspartylchlorin-e6

Mono-(l)-aspartylchlorin-e6 (also known as Talaporfin, NPe6, MACE, and most recently LS-11) is a potent sensitizer for photodynamic therapy that is currently undergoing clinical trials. Using a combination of unambiguous partial synthesis from pheophytin-a and methyl pheophorbide-a, NMR spectroscopy, and single crystal X-ray diffraction, the structure of mono-(l)-aspartylchlorin-e6 is definitively shown to be the isomer in which the aspartyl residue is attached at the 152-side chain position. This conclusion is contrary to earlier assumptions, but affirms the conclusions of a study based on NMR spectroscopy; a rationale for the unique formation of the 152-aspartyl derivative is proposed.

Synthesis of new derivatives of protoporphyrin IX and chlorophyll a

The vinyl groups in protoporphyrin IX and chlorophyll a derivatives were selectively transformed into hydroxymethyl and acetoxymethyl substituents. The reactivities of β-hydroxymethyl and β-acetoxymethyl groups in porphyrins and chlorins toward nucleophilic reagents were compared for the first time using the reaction with acetylacetone as an example. Peripheral acetylacetone moieties in porphyrins and chlorins were shown to be promising as building blocks for generation of exo heterocyclic structures.