A series of novel purpurinimides with long wavelength absorption were designed and synthesized to develop novel and potential photosensitizers. These compounds were investigated through reduction, oxidation, rearrangement reaction and amidation reactions of methyl pheophorbide a. They demonstrated a considerable bathochromic shift of the major absorption band in the red region of the optical spectrum (695-704 nm). Newly synthesized purpurinimides were screened for their antitumor activities, and showed higher photodynamic efficiency against A549 cell lines as compared to purpurin-18 methyl ester. The results revealed the novel purpurinimides could be potential photosensitizers.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4057721 | PMC |
http://dx.doi.org/10.3390/ijms15058091 | DOI Listing |
Int J Mol Sci
May 2014
Photodynamic Therapy (PDT) Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Korea.
Bioorg Med Chem Lett
March 2012
PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea.
Using stereoselective aldol-like condensation as a key methodology, a series of chlorophyll a-based long wavelength cationic chlorins were synthesized using methyl pyropheophorbide a (MPPa) and purpurin-18-N-methoxylimide methyl ester as starting materials. Such long wavelength cationic chlorins possess covalently linked cationic moieties (pyridinium or quinolinium) on the peripheral of their tetrapyrrole macrocycles. It was found that all long wavelength cationic chlorins showed their longest absorption maxima in the range of 712-763nm, making them potential photosensitizers in photodynamic therapy.
View Article and Find Full Text PDFJ Org Chem
January 2009
Chemistry Division, PDT Center, Cell Stress Biology, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
To investigate the electrochemical properties of purpurinimide dyads and electron transfer sites for their reduction and oxidation, a series of dimers with variable C-C linkages were synthesized. For the preparation of these novel structures, the formyl and 2-formylvinyl substituents were regioselectively introduced at positions 3 and 20 of Ni(II) purpurinimides by the Vilsmeier reaction. The Ni(II) complexes were then subjected to the McMurry reaction under two different conditions with unexpected results.
View Article and Find Full Text PDFMol Pharm
August 2007
Photodynamic Therapy Center, Department of Dermatology, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
A lactose moiety was regioselectively introduced at various positions of N-hexyl-mesopurpurinimide (a class of chlorin containing a fused six-membered imide ring system, lambda(max): 700 nm) to investigate the effect of its presence and position on photosensitizing efficacy. The resulting novel structures produced a significant difference in in vitro and in vivo efficacy. Among the positional isomers in which the lactose moiety was introduced at positions 3, 8, and 12, the 3-lactose purpurin-18-N-hexylimide produced the best efficacy.
View Article and Find Full Text PDFBioorg Med Chem Lett
July 2000
Photodynamic Therapy Center, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.
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.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!