Effect of substituents on Stokes shift of BODIPY and its application in designing bioimaging probes

Zhu, Xiaoyan; Yao, Hui-Wen; Fu, Yu-Jia; Guo, Xiao‐Feng; Hong, Wei

doi:10.1016/j.aca.2018.10.038

Cited by 27 publications

(16 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The maximum excitation and emission wavelengths of compound 1 were determined to be 497.5 and 508.5 nm, respectively (Supporting Figure 12). The small Stokes shift (∼11 nm) is characteristic of BODIPY compounds, which undergo little change in geometry upon photoexcitation. , The quantum yield of compound 1 (Φ) was determined in 0.1 M NaOH relative to fluorescein and found to be 0.03 (Supporting Figure 13) which is within the wide range of previously reported quantum yields for BODIPY compounds. − The electronic absorption profile of compound 1 showed an intense band at the wavelength used for photoactivation, 365 nm (ε = 10500 M –1 cm –1 ; Figure ; Supporting Figure 14 and Supporting Tables 1 and 2).…”

supporting

confidence: 63%

PhotoTag: Photoactivatable Fluorophores for Protein Labeling

2020

View full text Add to dashboard Cite

We report experimental studies on the development of photoactivatable fluorophores for rapid, light-induced synthesis of protein conjugates. Proof-of-concept studies demonstrated that electronic excitation of photoactivatable BODIPY-ArN3 (1) in the presence of different proteins leads to efficient labeling in less than 10 min. After synthesis and isolation of the fluorescently tagged protein, photochemical conversion yields using human serum albumin and onartuzumab were 47 ± 7% and 42 ± 5%, respectively.

show abstract

supporting

confidence: 63%

PhotoTag: Photoactivatable Fluorophores for Protein Labeling

2020

View full text Add to dashboard Cite

show abstract

“…Figure a demonstrated the UV–vis absorption and fluorescence (FL) spectra of BOPHY-2TPA in DMSO. When comparing the absorption and FL emission spectra, we could see that the BOPHY-2TPA could afford a large Stokes shift (∼110 nm), which effectively avoided the self-absorption issues encountered in the BODIPY photosensitizers Figure S7 showed a small Stokes shift (∼40 nm) of compound 3 , indicating that the introduction of TPA caused the large Stokes shift.…”

Section: Resultsmentioning

confidence: 92%

“…Photodynamic therapy (PDT) with minimal invasion and high selectivity has attracted wide attention in cancer treatment. , In the PDT process, the photosensitizers could generate reactive oxygen species (ROS) that exhibit high cytotoxicity to broad-spectrum tumors upon illumination. , To date, the photosensitizers for PDT mainly consist of porphyrin and its derivatives, boron dipyrromethene (BODIPY) derivatives, and ruthenium (Ru)-based complexes. − BODIPY and its derivatives have attracted notable interest in PDT due to their excellent photophysical properties, such as strong visible absorption, high singlet oxygen quantum yields (QYs), and good photostability. ,,− Up to now, many BODIPY derivatives have been synthesized and exploited as fluorescent probes , or PDT photosensitizers. − However, there are some limitations to hinder their clinical translation. First, BODIPY derivatives exhibit a narrow Stokes shift of about 10 nm . This small Stokes shift could induce self-absorption in the solid or aggregation state.…”

Section: Introductionmentioning

confidence: 99%

BOPHY-Based Aggregation-Induced-Emission Nanoparticle Photosensitizers for Photodynamic Therapy

Liu

Wei

et al. 2021

ACS Appl. Nano Mater.

View full text Add to dashboard Cite

Photosensitizers for photodynamic therapy (PDT) of cancer have been widely investigated over the past decades. However, the notorious aggregation-caused quenching (ACQ) effect limits their further biological applications. In this work, we have designed and reported a photosensitizer BOPHY-2TPA. The formed photosensitizer BOPHY-2TPA was a donor–acceptor–donor (D–A–D) structure with the BOPHY as an acceptor core and two triphenylamine (TPAs) as the electron donor units. The BOPHY-2TPA exhibited a large Stokes shift and excellent photoinduced 1O2 generation capabilities. Besides, the twisted structure of TPAs endowed the BOPHY-2TPA with intrinsic AIE properties, which effectively avoided the ACQ effect. Because of these prominent features, the BOPHY-2TPA aggregates encapsulated with biocompatible Pluronic P123 in aqueous solution showed high PDT antitumor efficiency.

show abstract

“…This increase in Stokes shift has previously been observed for BODIPYs carrying phenyl substituent in the 3 and 5 positions, although not to that great extent. 43 …”

Section: Resultsmentioning

confidence: 99%

Effect of the Aza-N-Bridge and Push–Pull Moieties: A Comparative Study between BODIPYs and Aza-BODIPYs

et al. 2022

View full text Add to dashboard Cite

In the field of fluorescent dyes, difluoroboron-dipyrromethenes (BODIPY) have a highly respected position. To predict their photophysical properties prior to synthesis and therefore to successfully design molecules specifically for one’s needs, a solid structure–function understanding based on experimental observations is vital. This work delivers a photophysical evaluation of BODIPY and aza-BODIPY derivatives equipped with different electron-withdrawing/-donating substituents. Using combinatorial chemistry, pyrroles substituted with electron-donating/-withdrawing substituents were condensed together in two different manners, thus providing two sets of molecules. The only difference between the two sets is the bridging unit providing a so far lacking comparison between BODIPYs and aza-BODIPYs structural homologues. Replacing the meso -methine bridge with an aza-N bridge results in a red-shifted transition and considerably different, temperature-activated, excited-state relaxation pathways. The effect of electron-donating units on the absorption but not emission for BODIPYs was suppressed compared to aza-BODIPYs. This result could be evident in a substitution pattern-dependent Stokes shift. The outlook of this study is a deeper understanding of the structure–optics relationship of the (aza)-BODIPY-dye class, leading to an improvement in the de novo design of tailor-made molecules for future applications.

show abstract

Effect of substituents on Stokes shift of BODIPY and its application in designing bioimaging probes

Cited by 27 publications

References 49 publications

PhotoTag: Photoactivatable Fluorophores for Protein Labeling

PhotoTag: Photoactivatable Fluorophores for Protein Labeling

BOPHY-Based Aggregation-Induced-Emission Nanoparticle Photosensitizers for Photodynamic Therapy

Effect of the Aza-N-Bridge and Push–Pull Moieties: A Comparative Study between BODIPYs and Aza-BODIPYs

Contact Info

Product

Resources

About