Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation DOI

Huiquan Zuo,

Qinghua Wu, Xing Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8150 - 8155

Published: Nov. 3, 2023

Through a strong oxidant Pb(OAc)4 promoted oxidative nucleophilic hydrogen substitution, site-selective direct and stepwise cyanation of BODIPYs using tetrabutylammonium cyanide was developed to give α-cyanated BODIPY derivatives. Characterization optical electrochemical properties these dyes provides substantial enhancement the electron affinity, with reduction potential LUMO level as low -0.04 V -4.43 eV, respectively. Radical anions electron-deficient 3,5-dicyanated were characterized by absorption EPR spectroscopy.

Language: Английский

Research advances in BODIPY-assembled supramolecular photosensitizers for photodynamic therapy DOI
Jun Wang, Qingbao Gong, Lijuan Jiao

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 496, P. 215367 - 215367

Published: Aug. 25, 2023

Language: Английский

Citations

80

J‐Aggregation Strategy toward Potentiated NIR‐II Fluorescence Bioimaging of Molecular Fluorophores DOI
Xiaoming Hu,

Caijun Zhu,

Fengwei Sun

et al.

Advanced Materials, Journal Year: 2023, Volume and Issue: 36(1)

Published: Aug. 1, 2023

Molecular fluorophores emitting in the second near-infrared (NIR-II, 1000-1700 nm) window with strong optical harvesting and high quantum yields hold great potential for vivo deep-tissue bioimaging high-resolution biosensing. Recently, J-aggregates are harnessed to engineer long-wavelength NIR-II emitters show unique superiority tumor detection, vessel mapping, surgical navigation, phototheranostics due their bathochromic-shifted bands required slip-stacked arrangement aggregation state. However, despite preliminary progress of theoretical study structure-property relationships, further paradigms remain scarce lack on aggregated fashion. In this effort, how utilize specific molecular structure form packing motifs J-type exciton coupling is emphatically elucidated. First, several regulating strategies achieve containing intermolecular interactions external conditions positively summarized deeply analyzed. Then, recent reports theranostics systematically provide a clear reference direction promoting development organic fluorophores. Eventually, prospective efforts ameliorating clinical practices outlined.

Language: Английский

Citations

68

Xanthene, cyanine, oxazine and BODIPY: the four pillars of the fluorophore empire for super-resolution bioimaging DOI
Soham Samanta, Kaitao Lai,

Feihu Wu

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(20), P. 7197 - 7261

Published: Jan. 1, 2023

In the realm of biological research, invention super-resolution microscopy (SRM) has enabled visualization ultrafine sub-cellular structures and their functions in live cells at nano-scale level, beyond diffraction limit, which opened up a new window for advanced biomedical studies to unravel complex unknown details physiological disorders level with unprecedented resolution clarity. However, most SRM techniques are highly reliant on personalized special photophysical features fluorophores. recent times, there been an surge development robust fluorophore systems various imaging techniques. To date, xanthene, cyanine, oxazine BODIPY cores have authoritatively utilized as basic units small-molecule-based organic fluorescent probe designing strategies owing excellent characteristics easy synthetic acquiescence. Since future next-generation will be decided by availability probes these four building blocks play important role progressive design, is urgent need review advancements fluorophores different methods based dye cores. This article not only includes comprehensive discussion about developments emphasis effective integration into cell bio-imaging applications but also critically evaluates background each highlight merits demerits towards developing newer SRM.

Language: Английский

Citations

63

Photoactivation Inducing Multifunctional Coupling of Fluorophore for Efficient Tumor Therapy In Situ DOI
Weijie Zhang,

Yunxia Lv,

Fangjun Huo

et al.

Advanced Materials, Journal Year: 2024, Volume and Issue: 36(23)

Published: Feb. 15, 2024

Abstract Photoactivatable molecules, with high‐precision spatialtemporal control, have largely promoted bioimaging and phototherapy applications of fluorescent dyes. Here, the first photoactivatable sensor ( BI ) is described that can be triggered by broad excitation light (405–660 nm), which further undergoes intersystem crossing H‐atom transfer processes to forming superoxide anion radicals (O 2 −• carbon radicals. Particularly, photoinduced gain carbon‐centered BI• allows for radical‐radical coupling afford combined crosslink product BI─BI ), would oxidized in presence O produce an extended conjugate system near infrared emission (820 nm). Besides, photochemically generated Cy─BI possesses ultra‐high photothermal conversion efficiency up 90.9%, optimized potential. What′s more, Western Blot assay reveals both photoproduct efficiently inhibit expression CHK1, irradiation induces apoptosis ultimately enhances phototherapeutic effects. Thus, combination cell cycle block inducing apoptosis, photodynamic therapy treatments significantly suppress solid tumor vivo antitumor efficacy explorations. This a novel finding developing as well applicability photoimaging tumor‐related areas.

Language: Английский

Citations

19

Recent Advances in Fluorescent Probes for Cancer Biomarker Detection DOI Creative Commons

Mingce Tian,

Riliga Wu,

Caihong Xiang

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(5), P. 1168 - 1168

Published: March 6, 2024

Many important biological species have been identified as cancer biomarkers and are gradually becoming reliable targets for early diagnosis late therapeutic evaluation of cancer. However, accurate quantitative detection remains challenging due to the complexity systems diversity development. Fluorescent probes extensively utilized identifying substances their notable benefits being non-invasive, quickly responsive, highly sensitive selective, allowing real-time visualization, easily modifiable. This review critiques fluorescent used detecting imaging over last five years. Focuses made on design strategies small-molecule nano-sized probes, construction methods fluorescence sensing platforms, further applications in multiple biomarkers, including enzymes, reactive oxygen species, sulfur microenvironments. aims guide development excellent diagnostic promote broad application analysis diagnosis.

Language: Английский

Citations

19

Synthesis and Properties of Bright Red-to-NIR BODIPY Dyes for Targeting Fluorescence Imaging and Near-Infrared Photothermal Conversion DOI
Zhengxin Kang,

Weibin Bu,

Xing Guo

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(7), P. 3402 - 3410

Published: Feb. 8, 2024

An efficient synthesis of 3-pyrrolylBODIPY dyes has been developed from a rational mixture various aromatic aldehydes and pyrrole in straightforward condensation reaction, followed by situ successively oxidative nucleophilic substitution using one-pot strategy. These resultant 3-pyrrolylBODIPYs without blocking substituents not only exhibit the finely tunable photophysical properties induced flexible meso-aryl but also serve as valuable synthetic framework for further selective functionalization. As proof such potential, one dye (581/603 nm) through installation morpholine group is applicable lysosome-targeting imaging. Furthermore, an ethene-bridged 3,3′-dipyrrolylBODIPY dimer was constructed, which displayed near-infrared (NIR) emission extended to 1200 nm with large fluorescence brightness (2840 M–1 cm–1). The corresponding nanoparticles (NPs) afforded high photothermal conversion efficiency (PCE) value 72.5%, eventually resulting favorable photocytotoxicity (IC50 = 9.4 μM) vitro eradication HeLa cells under 808 laser irradiation, highlighting their potential application therapy NIR window.

Language: Английский

Citations

11

BODIPY-based photocages: rational design and their biomedical application DOI
Heng Li, Jun Wang, Lijuan Jiao

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(45), P. 5770 - 5789

Published: Jan. 1, 2024

This highlight reviews various strategies for constructing BODIPY-based photocages, their photodecaging mechanisms, and applications in the biomedical field.

Language: Английский

Citations

11

Targeted Photoconvertible BODIPYs Based on Directed Photooxidation-Induced Conversion for Applications in Photoconversion and Live Super-Resolution Imaging DOI
Lazare Saladin, Victor Breton, Valentine Le Berruyer

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(25), P. 17456 - 17473

Published: June 11, 2024

Photomodulable fluorescent probes are drawing increasing attention due to their applications in advanced bioimaging. Whereas photoconvertible can be advantageously used tracking, photoswitchable constitute key tools for single-molecule localization microscopy perform super-resolution imaging. Herein, we shed light on a red and far-red BODIPY, namely, BDP-576 BDP-650, which possess both properties of conversion switching. Our study demonstrates that these pyrrolyl-BODIPYs convert into typical green- red-emitting BODIPYs perfectly adapted microscopy. We also showed this undergo Directed Photooxidation Induced Conversion, photoconversion mechanism recently introduced, where the pyrrole moiety plays central role. These unique features were develop targeted toward different organelles or subcellular units (plasma membrane, mitochondria, nucleus, actin, Golgi apparatus, etc.) using chemical targeting moieties Halo tag. notably BDP-650 could track intracellular vesicles over more than 20 min two-color imagings with laser scanning confocal microscopy, demonstrating its robustness. The switching photoconverters studied at level then successfully live epithelial cells neurons. Both membrane- mitochondria- decipher membrane 3D architecture mitochondrial dynamics nanoscale. This builds bridge between photoswitching undergoing directed photooxidation shows versatility efficacy

Language: Английский

Citations

11

Multiple photofluorochromic luminogens via catalyst-free alkene oxidative cleavage photoreaction for dynamic 4D codes encryption DOI Creative Commons

Lin Lu,

Bo Wu, Xinyuan He

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 31, 2024

Abstract Controllable photofluorochromic systems with high contrast and multicolor in both solutions solid states are ideal candidates for the development of dynamic artificial intelligence. However, it is still challenging to realize multiple photochromism within one single molecule, not mention good controllability. Herein, we report an aggregation-induced emission luminogen TPE-2MO2NT that undergoes oxidation cleavage upon light irradiation accompanied by tunable from orange blue time-dependence. The photocleavage mechanism revealed self-generation reactive oxidants driving catalyst-free oxidative process. A comprehensive analysis other comparative molecules demonstrates molecular scaffold can be easily modified extended. Further, microenvironmental controllability photoreaction polymer matrices enables fabrication fluorescence images 4D information codes, providing strategies advanced controllable encryption.

Language: Английский

Citations

9

Rational design of photofunctional dyes BODIPYs/aza-BODIPYs and applications for photocatalysis, photoelectric conversion and thermochromic materials DOI Creative Commons

Dongxiang Zhang,

Linxuan Liu, Xin Zhang

et al.

Resources Chemicals and Materials, Journal Year: 2024, Volume and Issue: 3(2), P. 103 - 122

Published: Jan. 15, 2024

4,4-Difluoro-4-bora-3a,4a-diaza-sindacene (BODIPY) is a sort of photofunctional dye which possesses advantages including strong light-capturing property, high photon-resistance, etc. Meso-N substituted aza-BODIPY crucial derivative BODIPY scaffold that has the favorable optical properties and significant spectral redshift. The photophysical can be tuned by molecular design, attenuation path excited state energy release absorbed light well controlled via structural modifications, enabling tailored application. It been extensively employed in life medicine fields fluorescence imaging diagnosis, photodynamic therapy photosensitizer photothermal reagent so forth. Extensive research review have performed these areas. However, BODIPYs/aza-BODIPYs role energy, catalysis, optoelectronics, photo-responsive materials other fields. Nevertheless, there are relatively few studies reviews on modification application based BODIPY/aza-BODIPY scaffold. Herein, this we summarized aforementioned fields, with regulation as foundation utilization above objective, intention providing inspiration for exploration innovative field resource conversion functional materials.

Language: Английский

Citations

7