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Issue 38, 2018
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Design and synthesis of a 4-aminoquinoline-based molecular tweezer that recognizes protoporphyrin IX and iron(iii) protoporphyrin IX and its application as a supramolecular photosensitizer

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Abstract

We report on the design and synthesis of a new type of 4-aminoquinoline-based molecular tweezer 1 which forms a stable host–guest complex with protoporphyrin IX (PPIX) via multiple interactions in a DMSO and HEPES buffer (pH 7.4) mixed solvent system. The binding constant for the 1 : 1 complex (K11) between 1 and PPIX is determined to be 4 × 106 M−1. Furthermore, 1 also forms a more stable complex with iron(III) protoporphyrin IX (Fe(III)PPIX), the K11 value for which is one order of magnitude greater than that for PPIX, indicating that 1 could be used as a recognition unit of a synthetic heme sensor. On the other hand, the formation of the stable PPIX·1 complex (supramolecular photosensitizer) prompted us to apply it to photodynamic therapy (PDT). Cell staining experiments using the supramolecular photosensitizer and evaluations of its photocytotoxicity indicate that the PDT activity of PPIX is improved as the result of the formation of a complex with 1.

Graphical abstract: Design and synthesis of a 4-aminoquinoline-based molecular tweezer that recognizes protoporphyrin IX and iron(iii) protoporphyrin IX and its application as a supramolecular photosensitizer

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Supplementary files

Article information


Submitted
15 May 2018
Accepted
14 Aug 2018
First published
31 Aug 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 7455-7467
Article type
Edge Article

Design and synthesis of a 4-aminoquinoline-based molecular tweezer that recognizes protoporphyrin IX and iron(III) protoporphyrin IX and its application as a supramolecular photosensitizer

Y. Hisamatsu, N. Umezawa, H. Yagi, K. Kato and T. Higuchi, Chem. Sci., 2018, 9, 7455
DOI: 10.1039/C8SC02133C

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