Pyrrolopyrrole aza boron dipyrromethene based two-photon fluorescent probes for subcellular imaging

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal

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Author(s)

  • Yimin Zhou
  • Chao Ma
  • Nengyue Gao
  • Qiong Wang
  • Kam Sing Wong
  • Qing-Hua Xu
  • Takumi Kinoshita
  • Dennis K. P. Ng

Related Research Unit(s)

Detail(s)

Original languageEnglish
Pages (from-to)5570-5581
Journal / PublicationJournal of Materials Chemistry B
Volume6
Issue number35
Online published16 Aug 2018
Publication statusPublished - 21 Sep 2018

Abstract

A series of pyrrolopyrrole aza boron dipyrromethene derivatives have been designed and synthesised as two-photon fluorescent probes. The bisalkynyl analogues, having a donor-π-donor quadrupolar skeleton, show a red-shifted Q band at ca. 700 nm in toluene and a two-photon absorption (TPA) cross-section up to 2349 GM at 1040 nm. To enable these dyes to be used for subcellular imaging, a branched oligoethylene glycol unit has been introduced to enhance their hydrophilicity and biocompatibility, and a potential organelle-selective group, namely triphenylphosphonium or morpholine moiety has also been added with a view to targeting the mitochondria or lysosomes respectively. The resulting conjugates are essentially non-aggregated in deionised water, exhibiting an intense Q band at 668 nm and a TPA cross-section up to 384 GM at 1040 nm. These spectral features have been analysed using density functional theory calculations, which suggest that the TPA is mainly due to the S0 → S2 transition. In the subcellular imaging study, it has been found that the triphenylphosphonium-containing derivative can localise in the lysosomes of HeLa human cervical carcinoma cells, which may be a result of its positive charge and the negative logP value (-2.46, P = partition coefficient), while the morpholine-substituted analogue does not exhibit preferential subcellular localisation.

Citation Format(s)

Pyrrolopyrrole aza boron dipyrromethene based two-photon fluorescent probes for subcellular imaging. / Zhou, Yimin; Ma, Chao; Gao, Nengyue; Wang, Qiong; Lo, Pui-Chi; Wong, Kam Sing; Xu, Qing-Hua; Kinoshita, Takumi; Ng, Dennis K. P.

In: Journal of Materials Chemistry B, Vol. 6, No. 35, 21.09.2018, p. 5570-5581.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journal