Water-soluble and fluorescent dendritic perylene bisimides for live-cell imaging

Gao, Baoxiang; Li, Hongxia; Liu, Hongmei; Zhang, Licui; Bai, Qianqian; Ba, Xinwu

doi:10.1039/c1cc00058f

Cited by 94 publications

(54 citation statements)

References 37 publications

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“…Spectral changes such as a broader and less structured absorption spectrum as well as a reduced absorption coefficient upon aggregation are due to strong excitonic interactions between the PBI chromophores . Supressing aggregation of perylene derivatives by shielding the PBI chromophore, however, can result in comparable fluorescence quantum yields in water and organic solvents . Similar behaviour was observed for Newkome dendronized perylene derivatives ( 34 ) by Hirsch et al; first generation Newkome dendronized PBIs aggregated into irregular architectures and second and larger generation PBIs dissolved molecularly.…”

Section: Nanoparticles Based On Self‐assembled π‐Conjugated Small Molsupporting

confidence: 55%

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Schill

Schenning

Brunsveld

2015

Macromol. Rapid Commun.

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Since the development of supramolecular chemical biology, self-organised nano-architectures have been widely explored in a variety of biomedical applications. Functionalized synthetic molecules with the ability of non-covalent assembly in an aqueous environment are typically able to interact with biological systems and are therefore especially interesting for their use in theranostics. Nanostructures based on π-conjugated oligomers are particularly promising as theranostic platforms as they bear outstanding photophysical properties as well as drug loading capabilities. This Feature Article provides an overview on the recent advances in the self-assembly of intrinsically fluorescent nanoparticles from π-conjugated small molecules such as fluorene or perylene based chromophores for biomedical applications.

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Section: Nanoparticles Based On Self‐assembled π‐Conjugated Small Molsupporting

confidence: 55%

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Schill

Schenning

Brunsveld

2015

Macromol. Rapid Commun.

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“…Therefore, several attempts have been performed in order to increase their solubility in aqueous media, either with functionalization in the bay region [12][13][14][15][16] or at the side imide groups. [17][18][19][20][21][22][23][24][25] Recently, we have introduced a series of highly water-soluble PBIs containing anionic (R 1 ) or cationic (R 2 ) Newkome dendronized substituents -representative examples are given in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

et al. 2014

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The synthesis, characterization and metal complexation of a new class of perylene bisimides (PBIs) as an integral part of ethylenediaminetetraacetic acid (EDTA) are reported. The simplest representative, namely derivative 1a, was synthesized both by a convergent as well as a direct approach while the elongated derivatives, 1b and 1c, were obtained only via a convergent synthetic pathway. All these new prototypes of water-soluble perylenes are bolaamphiphiles and were fully characterized by 1 H-and 13 C-NMR spectroscopy, matrix assisted laser desorption ionization-time of flight (MALDI-TOF) mass spectrometry and IR spectroscopy. In order to acquaint ourselves with the behaviour in solution of our PBIs bearing dendritic wedges, the simplest derivative, 1a, was chosen and tested by means of UV/Vis and fluorescence spectroscopy as well as by zeta-potential measurements. A photoexcitation induced intramolecular photo-electron transfer (PET) can be observed in these molecules. Therefore their potential applications as sensors can be imagined. Model compound 1a efficiently coordinates trivalent metal cations both in water and dimethyl sulfoxide (DMSO). Significantly, the effects of the complexation strongly depend on the aggregation state of the PBI molecules in solution. As a matter of fact, in water, the presence of M 3+ ions triggers the formation of light emitting supramolecular aggregates (excimers). On the other hand, in DMSO-rich solutions metal complexation leads to the suppression of the PET and leads to a strong fluorescence enhancement.

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“…[12,25] In most cases, the fluorescence emission has remained low, likely on account of p-p stacking. [26] To efficiently suppress aggregation, steric encumbrance introduced by substituents in the "bay region" [26][27][28] or large dendrons at the diimide sites [29,30] are generally required, which is substantially more demanding from the synthesis and purification point of view. [26] To efficiently suppress aggregation, steric encumbrance introduced by substituents in the "bay region" [26][27][28] or large dendrons at the diimide sites [29,30] are generally required, which is substantially more demanding from the synthesis and purification point of view.…”

mentioning

confidence: 99%

Strongly Fluorescent, Switchable Perylene Bis(diimide) Host–Guest Complexes with Cucurbit[8]uril In Water

et al. 2012

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Supramolecular complexation of perylene bis(diimide) (PDI) dyes with the macrocyclic host cucurbit[8]uril (CB[8]) prevents self-aggregation of the dye molecules and enables their use as highly (photo)chemically stable, strongly-emitting fluorophores in water. The complexes are stimuli-responsive to binders and can be electrochemically cycled, leading to reversible on-off fluorescence switching and access to noncovalent formation of higher-order architectures in water.

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Water-soluble and fluorescent dendritic perylene bisimides for live-cell imaging

Abstract: We prepared dendritic perylene bisimide probes with triblock structures: perylene bisimides fluorescence cores, branched oligo(glutamic acid)s and polyethylene glycol chains. These probes showed good water solubility, low cytotoxicity and strong fluorescence in live cells.

Cited by 94 publications

References 37 publications

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Self-Assembled Fluorescent Nanoparticles from π-Conjugated Small Molecules: En Route to Biological Applications

Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

Strongly Fluorescent, Switchable Perylene Bis(diimide) Host–Guest Complexes with Cucurbit[8]uril In Water

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