5111-07-9

Upstream product

• 186581-53-3 diazomethane 
• 603-17-8 pheophytin-a 
• 5594-30-9 pheophorbide a methyl ester 
• 6453-67-4 pyropheophorbide a methyl ester 
• 5594-30-9 14-ethyl-3-(2-methoxycarbonyl-ethyl)-4,8,13,18-tetramethyl-20-oxo-9-vinyl-23H,25H-phorbine-21-carboxylic acid methyl ester 
• 5594-30-9 methylpheophorbide a 
• 25465-77-4 purpurin 18 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 15592-17-3 chlorin e6 trimethyl ester 
• 6453-67-4 methyl pyropheophorbide a 
• 67-56-1 methanol 

Relevant academic research and scientific papers

LiOH promoted allomerization of pyropheophorbide a. A convenient synthesis of 132-oxopyropheophorbide a and its unusual enolization

Treatment of pyropheophorbide a with aqueous LiOH-THF gave the corresponding enolate, which on in situ oxidation produced the corresponding 132-oxo derivative in 79% yield; prolonged autoxidation gave purpurin-18 and purpurin-5 as major products and a mechanism for the formation of 12-formyl derivative from 132-oxopyropheophorbide a under unusual enolization is discussed; the electronic absorption spectroscopy data of the enolic intermediates showed a considerable perturbation in the π-systems of the macrocycle.

Synthesis of Derivatives of chlorin P6 trimethyl ester

The Vilsmeier reaction of nickel(II) chlorin P6 trimethyl ester with 3-dimethyl-aminoacrolein yielded nickel(II) chlorin P6 20-(2-formylvinyl) trimethyl ester and nickel(II) chlorin P6 3-(1-hydroxyethyl)-3-devinyl-20-(2-fo

Synthesis, optical properties and preliminary in vitro photodynamic effect of pyridyl and quinoxalyl substituted chlorins

A series of chlorophyll a-based chlorins conjugated with pyridyl or quinoxalyl group at different positions were synthesized, characterized and evaluated for their photodynamic effect in vitro. It was found that all the pyridyl and quinoxalyl chlorins showed promising photocytotoxicities but nontoxic without irradiation in HeLa cells, and the substituted types and positions had a significant influence on the photocytotoxicities of the chlorophyll a-based chlorins. All the chlorins with a pyridyl group at the C-D ring end exhibited relatively high photocytotoxicity as compared to those with 32-pyridyl. Among them, compound 12 conjugated with a pyridyl group at its C12 position showed the best photodynamic effect in HeLa cells with an IC50 value of 0.033 μM. These facts, associated with the relative high long wavelength absorptions of those chlorins may provide valuable ways to design and prepare promising photosensitizers for application in photodynamic therapy.

Mitochondrial Targeting Cationic Purpurinimide–Polyoxometalate Supramolecular Complexes for Enhanced Photodynamic Therapy with Reduced Dark Toxicity

Polyoxometalates (POMs), that are well-defined metal-oxygen cluster anions, are functional molecules extensively used in various research applications. The synthesis of neutral purpurinimides, followed by conversion to cationic purpurinimides (CPIs), formed CPI–POM supramolecular complexes via electrostatic interactions between each CPI and the polyanionic POM. The cellular uptake of purpurinimides, CPIs, and their CPI–POMs in A549 and HeLa cell lines was confirmed by confocal laser scanning microscopy. CPIs showed concentration-dependent dark cytotoxicity; however, CPI–POMs exhibited reduced low dark cytotoxicity. After photoirradiation, CPIs and CPI–POMs revealed enhanced photodynamic therapy (PDT) compared to free purpurinimides against A549 and HeLa cells. The CPIs exhibit low cell viability by incorporating their PDT effect with intrinsic dark cytotoxicity; however, the CPI–POMs exhibited a POM delivery effect-based enhanced PDT activity in the supramolecular complex system with low dark cytotoxicity. In particular, the clicked CPI–POM revealed two times higher PDT activity compared with the clicked free CPI, due to the good delivery effect of POM.

Self-aggregation of synthetic zinc 3-hydroxymethyl-purpurin-18 and N-hexylimide methyl esters in an aqueous solution as models of green photosynthetic bacterial chlorosomes

Zinc 31-hydroxy-131-oxo-chlorins possessing a six-membered exo-ring attached at the 13- and 15-positions were prepared by modifying purpurin-18. These synthetic anhydride and imide self-aggregated in an aqueous THF solution to give large oligomers (J-aggregates) similarly with the corresponding natural and artificial chlorophylls possessing a five-membered E-ring. Copyright

Purpurinimides as photosensitizers: Effect of the presence and position of the substituents in the in vivo photodynamic efficacy

This study presents a novel approach for the regioselective synthesis of a series of alkyl ether analogues of purpurin-18-N-alkylimide. In the purpurinimide series, this is the first example which demonstrates that the presence and position of the substituents in the macrocycle makes a remarkable difference in the in vivo PDT efficacy. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis, photophysical properties, tumor uptake, and preliminary in vivo photosensitizing efficacy of a homologous series of 3-(1′-alkyloxy)-ethyl-3-devinylpurpurin-18-N-alkylimides with variable lipophilicity

Starting from methylpheophorbide-a, a homologous series of purpurinimides containing alkyl substituents at two different positions [as 3-(11-O-alkyl) and 132-N-alkyl] were synthesized. These compounds with variable lipophilicity (log P 5.32-16.44) exhibit long wavelength absorption near) λmax700 nm (ε: 45 000 in dichloromethane) with singlet oxygen (1O2) production in the range of 57-60%. The shifts in in vivo absorptions and tumor/skin uptake of these compounds were determined in C3H mice bearing RIF tumors by in vivo reflectance spectroscopy. The results obtained from a set of photosensitizers with similar lipophilicity (log P 10.68-10.88) indicate that besides the overall lipophilicity, the presence and position of the alkyl groups (O-alkyl vs N-alkyl) in a molecule play an important role in tumor uptake, tumor selectivity, and in vivo PDT efficacy. At present, all purpurinimide analogues are being evaluated at various doses, and experiments are underway to establish a quantitative structure-activity relationship on a limited set of compounds. The 1D and 2D NMR and mass spectrometry analyses confirmed the structures of the desired purpurinimides and the byproducts formed during various reaction conditions. The mechanisms of the formation of the unexpected 12-formyl- and 12-(hydroxymethyl)purpurinimides under certain reaction conditions are also discussed.

Synthesis of long-wavelength chlorins by chemical modification for methyl pyropheophorbide-a and their in vitro cell viabilities

A series of novel chlorophyll-a homologs with long wavelength absorption were synthesized via modification of methyl pyropheophorbide-a used as starting material. For introducing electron-withdrawing group methylenemalononitrile moiety was established on

Efficient synthesis and in vitro photodynamic anticancer study of new purpurinimide-hydrazone conjugates

A series of new purpurinimide-hydrazone conjugates were synthesized, and their in vitro anticancer efficacy against A549 lung cancer cell lines was evaluated. It was found that the incorporation of the hydrazone group to the purpurinimide could increase t

Synthesis of purpurin-18 imide derivatives from chlorophyll-a and -b by modifications and functionalizations along their peripheries

The methyl pheophorbide-a and methyl pheophorbide-b were used as starting materials and converted to purpurin-18 ester by ring-opening and rearrangement reaction in their exocyclic ring. N-Substituted purpurin-18 imides were obtained from purpurin-18 ester through amidation reaction of six-membered cyclic anhydride. Further chemical modifications along their peripheries were carried out by a variety of common reactions, including electrophilic substitution, Wittig reaction, allomerization and Vilsmeier reaction, to afford the title compounds with long-wavelength absorption. The structures of all new chlorins were characterized by elemental analysis, IR, UV-vis and 1H NMR spectra.