Issue 38, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
15 may 2018
Accepted
14 avq 2018
First published
31 avq 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 7455-7467

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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