Highly water-soluble, near-infrared emissive BODIPY polymeric dye bearing RGD peptide residues for cancer imaging

Zhu, Shilei; Zhang, Jingtuo; Janjanam, Jagadeesh; Bi, Jianheng; Vegesna, Giri K.; Tiwari, Ashutosh; Luo, Fen; Wei, Jianjun; Liu, Haiying

doi:10.1016/j.aca.2012.10.026

Cited by 43 publications

(35 citation statements)

References 23 publications

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“…36 Cells were plated on 12-well culture plates at a density of 1 × 10 5 cells/mL for live cell imaging. After 24 h incubation at 37 °C with a 5% CO 2 incubator, the media was removed and cells were rinsed three times with PBS.…”

Section: Methodsmentioning

confidence: 99%

Near-Infrared Fluorescent Probes with Large Stokes Shifts for Sensing Zn(II) Ions in Living Cells

et al. 2016

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We report two new near-infrared fluorescent probes based on Rhodol counterpart fluorophore platforms functionalized with dipicolylamine Zn(II)-binding groups. The combinations of the pendant amines and fluorophores provide the probes with an effective three-nitrogen-atom and one-oxygen-atom binding motif. The fluorescent probes with large Stokes shifts offer sensitive and selective florescent responses to Zn(II) ions over other metal ions, allowing a reversible monitoring of Zn(II) concentration changes in living cells, and detecting intracellular Zn(II) ions released from intracellular metalloproteins.

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Section: Methodsmentioning

confidence: 99%

Near-Infrared Fluorescent Probes with Large Stokes Shifts for Sensing Zn(II) Ions in Living Cells

et al. 2016

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“…However, reports on that specific topic are rather scarce [9]. The functionalization of polymers with peptide units of arginine-glycine-aspartic acid (RGD) has been under extensive research in recent years [10][11][12][13][14], and combinations of polymer-based materials with constrained pentacyclic peptides, like c(RGDfC) [15,16], have been reported [10,17]. The mechanism of RGD motif recognition and subsequent cell attachment is based on the presence of integrins on cell surfaces.…”

Section: Introductionmentioning

confidence: 99%

RGD-Functionalization of Poly(2-oxazoline)-Based Networks for Enhanced Adhesion to Cancer Cells

et al. 2014

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Poly(2-oxazoline) networks with varying swelling degrees and varying hydrophilicity can be synthesized from 2-ethyl-2-oxazoline, 2-nonyl-2-oxazoline, 2-9'-decenyl-2-oxazoline and 2,2'-tetramethylene-bis-2-oxazoline in one-pot/one-step strategies. These gels can be loaded with organic molecules, such as fluorescein isothiocyanate, either during the polymerization (covalent attachment of the dye) or according to post-synthetic swelling/deswelling strategies (physical inclusion of the dye). Surface functionalization of ground gels by thiol-ene reactions with cysteine-bearing peptides exhibiting the arginine-glycine-aspartic acid (RGD) motif yields microparticles with enhanced recognition of human cancer cells compared to healthy endothelial cells.

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“…[41][42][43][44] Indeed, in some instances, the functional groups used for aqueous solubility, for example, PEG, analogues of PEG, or peptides, also make the compound cell permeable. [45][46][47] Although individually the issues of small Stokes shift, red or NIR emission, and water solubility have all been overcome in BODIPY derivatives, there have been few reports of dyes that overcome all three issues and in which the probes have been demonstrated to be useful in cell imaging.…”

Section: Introductionmentioning

confidence: 99%

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

et al. 2013

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The synthesis, optical properties, and cellular uptake of a family of 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) derivatives that incorporate a naphthyridine substituent at the 8‐position of the BODIPY core and either alkyl, bromo, or dimethylamino aryl groups at the 2‐ and 6‐positions are described. The family of compounds is classified, based on their optical properties, into two types; Class I, compounds with alkyl substituents at the 2‐ and 6‐positions show intense solvent‐independent emission, which arises from the BODIPY core with no involvement of the naphthyridine. Class II, the dimethylaminoaryl‐containing compounds exhibit charge transfer transitions that lead to NIR fluorescence and remarkably large Stokes shifts, which make them potentially attractive in bioimaging. Class II compounds exhibit complex solvent dependence. There is evidence for dual fluorescence from multiple rotamers; this is rationalized with the aid of time‐dependant density functional theory (TDDFT) calculations. A representative compound from each class was PEGylated, which rendered them water soluble, but their photophysical properties were maintained in aqueous buffered media. The uptake of the PEGylated BODIPY compounds and the nonPEGylated parent compounds by live mammalian cells was compared by using confocal fluorescence microscopy and resazurin blue cytotoxicity assays were performed. All compounds tested exhibited good cell uptake, were largely nuclear excluding, and had low toxicity at 10 μM. This is to our knowledge the first demonstration of such a mega‐Stokes‐shifted BODIPY probe in cell imaging.

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Highly water-soluble, near-infrared emissive BODIPY polymeric dye bearing RGD peptide residues for cancer imaging

Cited by 43 publications

References 23 publications

Near-Infrared Fluorescent Probes with Large Stokes Shifts for Sensing Zn(II) Ions in Living Cells

Near-Infrared Fluorescent Probes with Large Stokes Shifts for Sensing Zn(II) Ions in Living Cells

RGD-Functionalization of Poly(2-oxazoline)-Based Networks for Enhanced Adhesion to Cancer Cells

Naphthyridyl‐Substituted 4,4‐Difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) Luminophores: Photophysics and Application as Molecular Imaging Probes in Live Cells

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