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 (K ₁₁) 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 K ₁₁ 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 photosensit

SUBMITTER: Hisamatsu Y 

PROVIDER: S-EPMC6180317 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature