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1.
ACS Appl Bio Mater ; 2(10): 4456-4463, 2019 Oct 21.
Article in English | MEDLINE | ID: mdl-35021405

ABSTRACT

Exogenous nucleic acids showed low efficiency regarding cellular uptake and low stability in biological conditions; therefore, a number of techniques have been developed to improve their basic properties. One of the best solutions is the application of nanosized particles consisting of oligonucleotides that penetrate the cell membrane without any additives and exhibit high stability in cells. In this report, we employed a simple approach to address the basic properties of nanoparticles of oligonucleotides in biological systems. We prepared BODIPY-labeled oligonucleotides that carried an exclusive modification at the strand end. BODIPY shows high hydrophobicity and fluorescent emission; therefore, the oligonucleotides formed nanosized aggregates in aqueous solution and their behaviors in cells or tissues were easily tracked. Detailed experiments revealed that aggregate formation was indispensable for the high cellular uptake of the oligonucleotides via scavenger-receptor-mediated endocytosis. In addition, the aggregates provided an efficient gene regulation in living cells and tumor tissues transplanted into mice.

2.
Bioorg Med Chem ; 26(16): 4595-4601, 2018 09 01.
Article in English | MEDLINE | ID: mdl-30131291

ABSTRACT

Ruthenium complexes are very useful phosphorescent probes for the visualization of hypoxia. We designed and synthesized three ruthenium complexes possessing bromopyrene, naphthalene, or anthracene units to improve the oxygen response. These ruthenium complexes provided strong phosphorescence under hypoxic conditions, while an increase in oxygen concentration led to a decrease in phosphorescence intensity. Among the ruthenium complexes, that with a bromopyrene unit (Ru-BrPy) had the best properties. This showed good cellular uptake and bright emission in cells, and had the highest sensitivity for molecular oxygen. Thus, Ru-BrPy is a promising candidate as a molecular probe for detecting cellular hypoxia.


Subject(s)
Coordination Complexes/chemistry , Fluorescent Dyes/chemistry , Oxygen/chemistry , Pyrenes/chemistry , Ruthenium/chemistry , A549 Cells , Cell Hypoxia , Cell Survival/drug effects , Coordination Complexes/metabolism , Coordination Complexes/toxicity , Fluorescent Dyes/metabolism , Humans , Microscopy, Fluorescence , Oxygen/analysis
3.
Chembiochem ; 19(9): 956-962, 2018 05 04.
Article in English | MEDLINE | ID: mdl-29468796

ABSTRACT

Molecular oxygen in living cells is distributed and consumed inhomogeneously, depending on the activity of each organelle. Therefore, tractable methods that can be used to monitor the oxygen status in each organelle are needed to understand cellular function. Here we report the design of a new oxygen-sensing probe for use in the cell nucleus. We prepared "Ru-Hoechsts", each consisting of a phosphorescent ruthenium complex linked to a Hoechst 33258 moiety, and characterized their properties as oxygen sensors. The Hoechst unit shows strong DNA-binding properties in the nucleus, and the ruthenium complex shows oxygen-dependent phosphorescence. Thus, Ru-Hoechsts accumulated in the cell nucleus and showed oxygen-dependent signals that could be monitored. Of the Ru-Hoechsts prepared in this study, Ru-Hoechst b, in which the ruthenium complex and the Hoechst unit were linked through a hexyl chain, showed the most suitable properties for monitoring the oxygen status. Ru-Hoechsts are probes with high potential for visualizing oxygen fluctuations in the nucleus.


Subject(s)
Bisbenzimidazole/chemistry , Cell Nucleus/chemistry , Coordination Complexes/chemistry , Luminescent Agents/chemistry , Oxygen/analysis , Ruthenium/chemistry , A549 Cells , Fluorescent Dyes/chemistry , Humans , Luminescent Measurements/methods , Optical Imaging/methods
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