CN-122010918-A - Mitochondrion-targeted fluorescent lighting type diarylethene organic compound and biological imaging application thereof

Abstract

The invention discloses a mitochondrion targeting fluorescent lighting type diaryl ethylene organic compound and application thereof in biological imaging, wherein the structure of the mitochondrion targeting fluorescent lighting type diaryl ethylene organic compound is shown as a general formula (1), R 1 is shown as an alkyl chain, and R 2 is shown as a mitochondrion targeting group in the general formula (1). All the fluorescence lighting type diaryl ethylene photochromic materials have good biocompatibility and can realize accurate mitochondrial targeting.

Inventors

• AI QI
• LI HONGLING
• LIU FEIFEI
• ZHENG LUYE
• Fang Zhongshu
• ZHOU SHENGHUA

Assignees

• 中国计量大学

Dates

Publication Date

20260512

Application Date

20251231

Claims (8)

1. 1. A mitochondria targeted fluorescent lighting type diarylethene organic compound is characterized in that the structure is shown as a general formula (1): In the general formula (1), R 1 is C1-C6 alkyl; In the general formula (1), R 2 is represented as a mitochondrial targeting group.
2. 2. The mitochondrial targeted fluorescent lighting type diarylethene organic compound according to claim 1, wherein R 1 in the general formula (1) represents one of the following structures: -CH 3 ,-C 2 H 5 ,-C 3 H 7 ,-C 4 H 9 ,-C 5 H 11 .
3. 3. the mitochondrial targeted fluorescent lighting type diarylethene organic compound according to claim 1, wherein R 2 in the general formula (1) represents one of the following structures:
4. 4. the mitochondrial targeted fluorescent lighting type diarylethene organic compound according to claim 1, which is one of the following specific compounds:
5. 5. the mitochondrial targeted fluorescent lighting type diarylethene of claim 4, wherein the diarylethene organic compound 11 has the following structural formula:
6. 6. Use of a mitochondrial targeted fluorescent light-up diarylethene according to any of claims 1-5 in the field of bioimaging.
7. 7. The use of claim 6, wherein the mitochondrial-targeted fluorescent-lit diarylethenes are used to prepare fluorescent probes.
8. 8. The use according to claim 7, wherein the fluorescent probe is used for selective imaging of intracellular mitochondria.

Description

Mitochondrion-targeted fluorescent lighting type diarylethene organic compound and biological imaging application thereof Technical Field The invention relates to a photochromic material, in particular to a mitochondrion targeting fluorescent lighting type diaryl ethylene photochromic material and a biological imaging application thereof. Background The biological imaging technology is used as a core tool for life science research, disease diagnosis and drug research and development, can intuitively present the dynamic process of the molecular level in organisms, and provides key support for analyzing the life activity mechanism and early disease screening. The fluorescence imaging technology has become one of the most widely used imaging means in the biomedical field by virtue of the advantages of high sensitivity, high space-time resolution, simple operation, small damage to biological samples and the like. The fluorescent probe is used as a core component of a fluorescent imaging technology, and the performance of the fluorescent probe directly determines the imaging quality and the application effect, so that the development of the fluorescent probe with high selectivity, high stability, low biotoxicity and targeting specificity is a research hot spot and a core requirement in the current biological imaging field. In many biological targets, mitochondria are used as an 'energy factory' of cells, participate in key life processes of cell respiration, energy metabolism, signal transduction, apoptosis and the like, and the structure and the function of the mitochondria are closely related to the occurrence and the development of various diseases (such as cancers, neurodegenerative diseases, cardiovascular diseases and the like). Therefore, the accurate targeted imaging of mitochondria is realized, the dynamic change and microenvironment parameters (such as membrane potential, active oxygen level and the like) of the mitochondria are monitored in real time, and the method has important significance for further researching relevant physiological and pathological mechanisms of the mitochondria and developing a novel disease diagnosis method. The diaryl ethylene compound is one kind of organic functional material with photochromic characteristic, and its molecular structure may undergo reversible cyclization/ring-opening isomerization reaction under the irradiation of ultraviolet light and visible light, with obvious change in absorption spectrum, fluorescence spectrum and other optical properties. The compound has the advantages of high photostability, strong photo-bleaching resistance, high response speed, long cycle service life and the like, and has been widely applied to the fields of optical switches, fluorescent sensors, super-resolution imaging and the like. The diarylethene structure is introduced into a fluorescent probe design, so that a fluorescent lighting type light response probe can be constructed, wherein the probe is in an open loop state when no ultraviolet light is irradiated, a fluorescent signal is weak, after ultraviolet light is excited, the probe undergoes cyclization isomerization, the fluorescent signal is obviously enhanced (namely a lighting effect), the characteristic can effectively reduce imaging background noise, and the detection sensitivity is improved. In addition, the molecular structure of the diarylethene compound can be flexibly regulated and controlled through chemical modification, and the probability is provided for realizing mitochondrial targeting and multi-response function integration. Disclosure of Invention Although diarylethenes present great potential in the field of photoresponsive fluorescent materials, the related studies of their application to mitochondrial targeted bio-imaging are still in the beginning, with significant blank in the prior art: (1) The design strategy of the diaryl ethylene compound with the characteristics of mitochondrial targeting and photochromic fluorescent lighting is lacking, the existing diaryl ethylene derivative has no definite biological targeting function, and the accurate positioning imaging of mitochondria is difficult to realize; (2) The existing combination of the mitochondrial targeting probe and the diarylethene structure has compatibility problems, for example, the introduction of the targeting group can damage the photochromic performance of the diarylethene, or the biocompatibility is reduced due to the unbalance of the lipid solubility and the water solubility of the probe molecule; (3) Diarylethene-based bioimaging probes capable of satisfying high targeting, high fluorescent lighting efficiency, excellent biocompatibility and responsiveness to mitochondrial microenvironment at the same time have not been developed. Therefore, aiming at the defects of the existing biological imaging probes and the application gap of the diarylethene compound in the biomedical field, the mitochondrial targeting fluorescent lighting