Cooperative nanoparticle H-type self-assembly of a bolaamphiphilic BODIPY derivative in aqueous medium

Rödle, Alexander; Lambov, Martin; Mück‐Lichtenfeld, Christian; Stepanenko, Vladimir; Fernández, Gustavo

doi:10.1016/j.polymer.2016.12.050

Cited by 29 publications

(27 citation statements)

References 37 publications

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“…[60] Aggregation studies of positively charged (LBDP4) and net neutral (LBDP5) long chain-substituted amphiphilic BODIPYs in water yielded the formation of Hand/or J-type aggregates. [25,26,28] Temperature-and concentration-dependent UV/Vis studies revealed that aggregation of LBDP4 occurs via a cooperative process, resulting in vesicles with a multilamellar wall structure. [25] In the case of LBDP5, only H aggregates were observed, this time leading to spherical nanoparticles by non-cooperative self-assembly.…”

Section: Previous Observations On Associationmentioning

confidence: 99%

“…reported NIR fluorescent nanoparticles formed by the J aggregation of hydrophobic BODIPY dyes in THF:water mixtures . Aggregation studies of positively charged ( LBDP4 ) and net neutral ( LBDP5 ) long chain‐substituted amphiphilic BODIPYs in water yielded the formation of H‐ and/or J‐type aggregates . Temperature‐ and concentration‐dependent UV/Vis studies revealed that aggregation of LBDP4 occurs via a cooperative process, resulting in vesicles with a multilamellar wall structure .…”

Section: Introductionmentioning

confidence: 99%

“…Among other popular dyes such as fluoresceins, rhodamines and cyanines, the applications and investigations involving BODIPYs have grown disproportionately high over the last two decades (Figure ) and the literature reporting the synthesis of new BODIPYs and a description of their optical and chemical properties in organic media is abundant . However, rather few efforts have been devoted to the study of their properties in aqueous solutions . This is surprising because on one hand the peculiarities of the application of BODIPYs in water are long since documented even by commercial suppliers yet on the other hand many of the aspired applications such as fluorescence labeling or sensing essentially require operation in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] However, rather few efforts have been devoted to the study of their properties in aqueous solutions. [18][19][20][21][22][23][24][25][26][27][28] This is surprising because on one hand the peculiarities of the application of BODIPYs in water are long since documented even by commercial suppliers [29] yet on the other hand many of the aspired applications such as fluorescence labeling or sensing essentially require operation in aqueous solution. The reason might be related to the fact that although they are intrinsically zwitterionic, BODIPYs have a rather hydrophobic character.…”

Section: Introductionmentioning

confidence: 99%

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On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

et al. 2019

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The tendency of boron‐dipyrromethene (BODIPY) dyes to associate in water is well known, and usually a cause for inferior fluorescence properties. Synthetic efforts to chemically improve BODIPYs’ water solubility and minimize this problem have been numerous in the past. However, a deeper understanding of the phenomena responsible for fluorescence quenching is still required. Commonly, the spectroscopic behaviour in aqueous media has been attributed to aggregate or excimer formation, with such works often centring on a single BODIPY family. Herein, we provide an integrating discussion including very diverse types of BODIPY dyes. Our studies revealed that even subtle structural changes can distinctly affect the association behaviour of the fluorophores in water, involving different photophysical processes. The palette of behaviour found ranges from unperturbed emission, to the formation of H or J aggregates and excimers, to the involvement of tightly bound, pre‐formed excimers. These results are a first step to a more generalized understanding of spectroscopic properties vs. structure, facilitating future molecular design of BODIPYs, especially as probes for biological applications.

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Section: Previous Observations On Associationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

et al. 2019

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“…In this study, three UBD (UBD-1-3) with different alkyl chain lengths (hexyl, heptyl, and octyl, respectively) were prepared to investigate the self-assembly behavior in aqueous solution [20,21]. Although nanoparticle formation was observed in all cases, the existence of a critical aggregation concentration (CAC) was indicative of the effect of the alkyl chain length.…”

Section: Introductionmentioning

confidence: 99%

Effect of Hydrophobicity on the Self-Assembly Behavior of Urea Benzene Derivatives in Aqueous Solution

et al. 2018

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Urea benzene derivatives (UBD) with amphiphilic side chains showed self-assembly behavior in aqueous solution to form nanoparticles~100 nm in size. Subsequent thermal treatment led to additional self-assembly of the nanoparticles due to dehydration of the amphiphilic side chains, producing microparticles. This self-assembly process was accompanied by a lower critical solution temperature (LCST) behavior, as revealed by the abrupt decrease in solution transmittance. In this study, three UBD (UBD-1-3) with different lengths of the alkyl segment in the amphiphilic side chain (namely, hexyl, heptyl, and octyl, respectively) were prepared to investigate the self-assembly behavior in aqueous solution. UBD-1-3 formed identical nanoparticles, with sizes in the 10~80 nm range but with different LCST values in the order 3 < 2 < 1. These results suggest a relationship between the hydrophobicity and the self-assembly behavior of UBD.

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A dual‐functional BODIPY‐based molecular rotor probe reveals different viscosity of protein aggregates in live cells

Shen

Jung

et al. 2022

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Aberrant protein aggregation leads to various human diseases, but little is known about the physical chemical properties of these aggregated proteins in cells. Herein, we developed a boron-dipyrromethene (BODIPY)-based HaloTag probe, whose conjugation to HaloTag-fused proteins allows us to study protein aggregates using both fluorescence intensity and lifetime. Modulation of BODIPY fluorophore reveals key structural features to attain the dual function. The optimized probe exhibits increased fluorescence intensity and elongated fluorescence lifetime in protein aggregates. Fluorescence lifetime imaging using this probe indicates that protein aggregates afford different viscosity in the forms of soluble oligomers and insoluble aggregates in live cells. The strategy presented in this work can be extended to enable a wide class of HaloTag probes that can be used to study a variety of physical properties of protein aggregates, thus helping unravel the pathogenic mechanism and develop therapeutic strategy.

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Cooperative nanoparticle H-type self-assembly of a bolaamphiphilic BODIPY derivative in aqueous medium

Cited by 29 publications

References 37 publications

On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

On the Aggregation Behaviour and Spectroscopic Properties of Alkylated and Annelated Boron‐Dipyrromethene (BODIPY) Dyes in Aqueous Solution

Effect of Hydrophobicity on the Self-Assembly Behavior of Urea Benzene Derivatives in Aqueous Solution

A dual‐functional BODIPY‐based molecular rotor probe reveals different viscosity of protein aggregates in live cells

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