Alternative synthesis of 3-acetyl, 3-epoxy, and 3-formyl chlorins from a 3-vinyl chlorin, methyl pyropheophorbide-a, via iodination

Oba, Toru; Masuya, Takuto; Yasuda, Satoru; Ito, Satoshi

doi:10.1016/j.bmcl.2015.05.024

Cited by 4 publications

(1 citation statement)

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“…Chlorophyll-a-based photosensitizers are attracting increased attention in PDT due to the high optical activity. Pyropheophorbide-a (PPa), which belongs to the chlorophyll-a compounds, is one of the most widely used agents with the advantages of high singlet oxygen generation, low skin toxicity, and light absorbance above 650 nm. , However, PPa has been characterized with poor solubility in water, which significantly limits its therapeutic efficacy in PDT . Furthermore, the physical encapsulation of PPa resulted in low loading capacity and significant leak of the drug that are not beneficial for in vivo treatment.…”

Section: Introductionmentioning

confidence: 99%

Tumor-Homing and Penetrating Peptide-Functionalized Photosensitizer-Conjugated PEG-PLA Nanoparticles for Chemo-Photodynamic Combination Therapy of Drug-Resistant Cancer

Feng

Jiang

Kang

et al. 2016

ACS Appl. Mater. Interfaces

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The combination of photodynamic therapy (PDT) and chemotherapy holds great potential in combating drug-resistant cancers. However, the major challenge that lies ahead is how to achieve high coloading capacity for both photosensitizer and chemo-drugs and how to gain efficient delivery of drugs to the drug-resistant tumors. In this study, we prepared a nanovehicle for codelivery of photosensitizer (pyropheophorbide-a, PPa) and chemo-drugs (paclitaxel, PTX) based on the synthesis of PPa-conjugated amphiphilic copolymer PPa-PLA-PEG-PLA-PPa. The obtained nanoparticles (PP NP) exhibited a satisfactory high drug-loading capacity for both drugs. To achieve effective tumor-targeting therapy, the surface of PP NP was decorated with a tumor-homing and penetrating peptide F3. In vitro cellular experiments showed that F3-functionalized PP NP (F3-PP NP) exhibited higher cellular association than PP NP and resulted in the strongest antiproliferation effect. In addition, compared with the unmodified nanoparticles, F3-PP NP exhibited a more preferential enrichment at the tumor site. Pharmacodynamics evaluation in vivo demonstrated that a longer survival time was achieved by the tumor-bearing mice treated with PP NP (+laser) than those treated with chemotherapy only or PDT only. Such antitumor efficacy of combination therapy was further improved following the F3 peptide functionalization. Collectively, these results suggested that targeted combination therapy may pave a promising way for the therapy of drug-resistant tumor.

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Section: Introductionmentioning

confidence: 99%