5111-07-9Relevant articles and documents
LiOH promoted allomerization of pyropheophorbide a. A convenient synthesis of 132-oxopyropheophorbide a and its unusual enolization
Kozyrev, Andrei N.,Dougherty, Thomas J.,Pandey, Ravindra K.
, p. 481 - 482 (1998)
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, optical properties and preliminary in vitro photodynamic effect of pyridyl and quinoxalyl substituted chlorins
Li, Jiazhu,Zhang, Xin,Liu, Yang,Yoon, Il,Kim, Dong-Kyoo,Yin, Jun-Gang,Wang, Jin-Jun,Shim, Young Key
, p. 1684 - 1690 (2015)
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.
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
Tamiaki, Hitoshi,Shimamura, Yasuhide,Yoshimura, Hideaki,Pandey, Suresh K.,Pandey, Ravindra K.
, p. 1344 - 1345 (2005)
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
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
Zheng,Potter,Camacho,Missert,Wang,Bellnier,Henderson,Rodgers,Dougherty,Pandey
, p. 1540 - 1559 (2001)
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.
Efficient synthesis and in vitro photodynamic anticancer study of new purpurinimide-hydrazone conjugates
Li, Jia Zhu,Li, Li,Kim, Jung Hwa,Cui, Bing Cun,Wang, Jin Jun,Shim, Young Key
, p. 264 - 270 (2011)
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
Efficient synthesis and in vitro PDT effect of purpurin-18-N-aminoimides
Cui, Bing Cun,Cha, Min Uk,Li, Jia Zhu,Park, Ho Sung,Yoon, Il,Shim, Young Key
, p. 3313 - 3317 (2010)
A simple and efficient synthetic route for making purpurin-18-N-aminoimides is described. The purpurin-18-Naminoimides are obtained by treatment of purpurin-18 methyl ester with various amines. These new compounds have long wavelength absorptions in the range of 706 - 711 nm. In preliminary screening, the purpurin-18-N-aminoimides have shown promising photosensitizing activity for the cancer cell by in vitro study in photodynamic therapy.
A new cyclic thioanhydride derived from chlorophyll a and its aurophilic properties
Grin, Mikhail,Kirin, Nikita,Mironov, Andrey,Pogorilyy, Viktor
, (2020/10/02)
The need to modify the chlorine macrocycle by additional exocycles is dictated by the desire to increase the stability of the pigment, improve its spectral characteristics, including the shift of the main absorption band to the long-wavelength region, as well as the introduction of chemically active groups for the introduction of other bioactive molecules. Replacing the oxygen atom in the purpurin-18 anhydride exocycle with a sulfur atom can be considered as a bioisosteric substitution, which should not strongly affect the spectral and biological properties of the photosensitizer, but may allow the implementation of new chemical modifications at the periphery of the macrocycle. In this paper, we propose a synthesis pathway for a derivative of naturally occurring chlorin that contains an additional thioanhydride cycle attached to the main macrocycle. We report the spectral characteristics of the compound and demonstrate the possibility of immobilization of chlorin p6 thioanhydride on gold nanoparticles (Au-NP).
Convenient peripheral aroyloxylation reactions of porphyrins and chlorophyll-a-based chlorins with benzoyl peroxide
Li, Jiazhu,Zhang, Peng,Yao, Nan-Nan,Zhao, Li-Li,Wang, Jin-Jun,Shim, Young Key
, p. 1086 - 1089 (2015/02/18)
A practical and efficient methodology for the formation of C-O bonds on the porphyrin/chlorin periphery was developed. The aroyloxy-substituted porphyrins and chlorins related to chlorophyll-a at the β- and meso-positions, respectively, were conveniently synthesized by the free radical substitution reaction with benzoyl peroxide and its homologs.
