Triarylboron-Based High Photosensitive Probes for Apoptosis Detection, Tumor-Targeted Imaging, and Selectively Inducing Apoptosis of Tumor Cells by Photodynamics

Abstract

Herein, a series of triarylboron-based fluorescent probes were developed for distinguishing apoptosis from living cells and even necrosis. They also demonstrate high photosensitivity because they can produce detectable reactive oxygen species (ROS) under an ultra-low light power density (1.5 mW/cm2). By changing the peripheral groups to regulate the performance, we identified a multifunctional probe, TAB-6-amyl, which can be used not only for selectively imaging apoptosis but also for the targeted imaging of SKOV-3 cells in vitro and in vivo. It could further specifically induce the apoptosis of SKOV-3 cells under light irradiation. During the study, we also found that TAB-6-amyl can cross the blood–brain barrier (BBB). Therefore, another probe based on this kind of structure, TAB-5-M-1-cRGD, was constructed for the targeted imaging of brain glioma cells and inducing their apoptosis. This study offers some promising tools for apoptosis detection and tumor photodynamic therapy (PDT).

Immuno-photodynamic Therapy (IPDT): Organic Photosensitizers and Their Application in Cancer Ablation

“…Apoptosis is a caspase-dependent process of programmed cell death, which controls the development, homeostasis, and immunity in multicellular organisms. , Facilitating apoptosis is one of the most active regulatory pathways to induce ICD. Due to the cancer cells being more sensitive to ROS than normal cells, apoptosis induced by IPDT would be more effective and avoid overtreatment .…”

Multicolor Adjustable B–N Molecular Switches: Simple, Efficient, Portable, and Visual Identification of Butanol Isomers

“…It is well known that boron (B) is a nonmetallic element in the third main group of the periodic table, and its valence electron structure is 2s 2 2p 1 . Obviously, the number of valence electrons of the B is smaller than the number of valence orbitals, thus exhibiting an electron-deficient nature, − This favors the formation of coordination compounds (complexes) of boron. For example, in an sp 2 hybrid covalent molecule, the remaining p z empty orbital of the B can act as a Lewis acid, accepting an external lone pair of electrons (X: oxygen (O), nitrogen (N), phosphorus (P)) to form an sp 3 hybrid tetrahedral complex (Lewis acid–base pair). , Therefore, this Lewis acid complex generally has additivity, such as boron trifluoride and ammonia gas molecules forming B ← N Lewis acid–base pair. ,, However, this B ← X complex is usually in a metastable state, such as when its surrounding environment (such as T, P, and L) changes, its B ← X bond is prone to breakage or bond formation, thereby releasing different photophysical properties. ,− Therefore, rational design and utilization of the metastable structure of the B ← X complex is expected to successfully construct novel fluorescent molecular switches.…”

CB[8]- and triarylboron-based supramolecular organic framework for microRNA detection, tumor-targeted drug delivery, and photodynamic therapy

“…37,38 Especially, in our previous studies, we have developed a class of highly photosensitive substances by functionalizing triarylboron compounds with pyridine-positive ion group. 39 Considering the positive charge and amphiphilicity of such molecules, it may be possible to self assemble with CB [8] to form SOF and further achieve microRNA recognition through competitive binding.…”