論文 - 詳細
| RRC ID | 44386 |
|---|---|
| 著者 | Kitagishi H, Hatada S, Itakura T, Maki Y, Maeda Y, Kano K. |
| タイトル | Cellular uptake of octaarginine-conjugated tetraarylporphyrin included by per-O-methylated β-cyclodextrin. |
| ジャーナル | Org Biomol Chem |
| Abstract |
This paper describes the synthesis, structural characterization and cellular uptake of a supramolecular 1 : 2 inclusion complex of meso-tetraphenylporphyrin having an octaarginine peptide chain (R8-TPP) and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (TMe-β-CD). R8-TPP was synthesized by 2 approaches: (1) on-resin conjugation of the N-terminal of octaarginine with 5-(4-carboxyphenyl)-10,15,20-triphenylporphyrin, followed by cleavage from the resin, and (2) Michael addition reaction between 5-[4-(3-maleimidopropylamido)phenyl]-10,15,20-triphenylporphyrin and cysteine-octaarginine peptide (Cys-Arg8). The R8-TPP obtained from both the approaches formed stable inclusion complexes with TMe-β-CD by which non-substituted phenyl groups at the 10- and 20-positions were included to form trans-type 1 : 2 inclusion complexes. The complexation prevented the self-aggregation of R8-TPP, which resulted in the solubilisation of R8-TPP in aqueous media. A cellular uptake study using HeLa cells showed that R8-TPP complexed with TMe-β-CD in a serum-free medium was efficiently taken up by the cells and uniformly dispersed in the cytosol. In the serum-containing medium, the R8-TPP-TMe-β-CD complex dissociated, and the serum protein bound R8-TPP. The R8-TPP-protein complex was localized in the endosomes of the cells. The cytosol-dispersed R8-TPP showed a higher photo-induced cytotoxicity than its endosome-trapped counterpart. |
| 巻・号 | 11(19) |
| ページ | 3203-11 |
| 公開日 | 2013-5-21 |
| DOI | 10.1039/c3ob27248f |
| PMID | 23584796 |
| MeSH | Cell Death / drug effects Cell Survival / drug effects Dose-Response Relationship, Drug HeLa Cells Humans Methylation Molecular Structure Oligopeptides / chemical synthesis Oligopeptides / chemistry Oligopeptides / pharmacology* Porphyrins / chemical synthesis Porphyrins / chemistry Porphyrins / pharmacology* Structure-Activity Relationship beta-Cyclodextrins / chemistry beta-Cyclodextrins / pharmacology* |
| IF | 3.412 |
| 引用数 | 18 |
| WOS 分野 | CHEMISTRY, ORGANIC |
| オルトメトリクス指標 |
オルトメトリクス指標項目
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| 最多言及媒体 | Patent(IFI CLAIMS) |
| 各媒体での言及数の合計 | 2 |
| 過去6か月間でのオルトメトリクス指標の変動値 | 0.0 |
| リソース情報 | |
| ヒト・動物細胞 | HeLa |