BODIPY as a Multifunctional Theranostic Reagent in Biomedicine: Self‐Assembly, Properties, and Applications

Abstract

owing to its large molar absorption coefficients, high emission quantum yields, satisfactory chemical stability, and high tunability of photophysical properties. [10,11] The conventional BODIPY core has good structural stability, in which BF 2 -chelated inhibits the rotation around the CN pyrrole bridging bonds, which enhances the structural rigidity and endows the system with fluorescence emission properties. [12] The BODIPY core has 8 covalently modified positions, which can be divided into pyrrole ring carbons, the meso-carbon, and the boron atom. [11,13,14] These abundant active sites provide lots of possibilities to expand the structure of BODIPY derivatives through functionalization and to tune their photophysical properties. [15] In the past few decades, the structural modification strategies of BODIPY units and the resulting effects have been systematically explored, [4,16] providing a solid research foundation for the current-stage design and construction of various functional BODIPY derivatives for different occasions. After decades of development, by virtue of the high molar extinction coefficient, longer wavelength absorbing, outstanding photosensitivity, satisfactory internal stability, better biocompatibility relative to inorganic dyes, high light-dark toxicity ratios, and preferable photothermal conversion efficiency (PCE), [4,[17][18][19] there has been considerable interest in exploring the application of BODIPY as photosensitizers (PSs) in the area of phototherapy, which involves the production of reactive The use of boron dipyrromethene (BODIPY) in biomedicine is reviewed. To open, its synthesis and regulatory strategies are summarized, and inspiring cutting-edge work in post-functionalization strategies is highlighted. A brief overview of assembly model of BODIPY is then provided: BODIPY is introduced as a promising building block for the formation of single-and multicomponent self-assembled systems, including nanostructures suitable for aqueous environments, thereby showing the great development potential of supramolecular assembly in biomedicine applications. The frontier progress of BODIPY in biomedical application is thereafter described, supported by examples of the frontiers of biomedical applications of BODIPY-containing smart materials: it mainly involves the application of materials based on BODIPY building blocks and their assemblies in fluorescence bioimaging, photoacoustic imaging, disease treatment including photodynamic therapy, photothermal therapy, and immunotherapy. Lastly, not only the current status of the BODIPY family in the biomedical field but also the challenges worth considering are summarized. At the same time, insights into the future development prospects of biomedically applicable BODIPY are provided.

Functional supramolecular aggregates based on BODIPY and aza-BODIPY dyes: control over the pathway complexity

“…In recent years, remarkable efforts have been devoted to the development of functionalities of BODIPY derivatives. [65][66][67][68][144][145][146][147][148] The molecular BODIPY and aza-BODIPY dyes have been investigated in a diverse range of applications, such as fluorescent probes, [149][150][151][152] ion recognition, 153,154 biological imaging, [155][156][157][158] photothermal and photodynamic therapy, [159][160][161][162][163][164] organic solar cells, 146 and liquid crystalline materials. 165 In this part we focus on those applications of (aza-)BODIPY dyes specifically connected with their self-assembly pathways.…”

Chiral amino acid modified boron-dipyrromethene nanoparticles with different photodynamic activities

“…BDPs are widely applied as PSs because of their excellent performances, including feasible modification. [37][38][39] To synthesize the BDPs modified with L-Asp and D-Asp, BDP-COOH was first synthesized, followed by the synthesis of BDP via iodine substitution reaction (Fig. S1, ESI †).…”

BODIPY-Based NO Probe for Macrophage-Targeted Immunotherapy Response Monitoring

“…Besides, BODIPY has better photochemical stability, molar absorption efficiency, and lower biological toxicity, which is suitable for clinical application. 24 More importantly, BODIPY with an aromatic primary amine-based structure has been reported for NO detection with less interference via a photoinduced electron transfer (PET) process. 25 Hence, the design and development of an easily accessible BODIPY-based NO probe could be highly promising for detecting TAMs-targeted immunotherapy in vivo.…”

“…With proper modification, the wavelength of BODIPY could shift to the red region, which has a deeper issue penetration. Besides, BODIPY has better photochemical stability, molar absorption efficiency, and lower biological toxicity, which is suitable for clinical application . More importantly, BODIPY with an aromatic primary amine-based structure has been reported for NO detection with less interference via a photoinduced electron transfer (PET) process .…”