Interaction of BODIPY dyes with bovine serum albumin: a case study on the aggregation of a click-BODIPY dye

Jameson, Laramie P.; Smith, Nicholas W.; Annunziata, Onofrio; Dzyuba, Sergei V.

doi:10.1039/c6cp00420b

Cited by 38 publications

(23 citation statements)

References 20 publications

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“…We may conclude that FBS, while facilitating the solubility of the control dye, effectively prevented its partitioning into the cells by providing a competing hydrophobic environment for H 4 BCH 3 to reside into. This is consistent with the reports of BODIPY complexation by BSA …”

Section: Resultssupporting

confidence: 94%

“…Influence of Serum Albumin in Monitoring H 4 BPMHC Response. Prior to testing the sensitivity of H 4 BPMHC in live cells under various levels of oxidative stress, and stimulated by a recent report illustrating the solubility and increased fluorescence of BODIPY dyes in the presence of bovine serum albumin (BSA) 33 we investigated the effect of fetal bovine serum (FBS) on the partitioning of our BODIPY fluorophores into adherent cells. Here, partitioning is reflected by the fluorescence of our control dye, H 4 BCH 3 , observed in cells using fluorescence microscopy.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…This is consistent with the reports of BODIPY complexation by BSA. 33 That FBS in solution competes with cellular membranes for the lipophilic dye H 4 BCH 3 (and presumably also for the lipophilic fluorogenic probe H 4 BPMHC) was additionally illustrated by a series of experiments where the staining solution of H 4 BCH 3 containing no FBS was removed, and addition of either fresh LCS, DMEM, or DMEM supplemented with 10% FBS took place. In the latter case, the control dye was rapidly depleted from the cell membranes, while only minor Previous imaging studies in DMEM supplemented with FBS precluded us from using dye concentrations below 1 μM.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Rate of Lipid Peroxyl Radical Production during Cellular Homeostasis Unraveled via Fluorescence Imaging

2017

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Reactive oxygen species (ROS) and their associated byproducts have been traditionally associated with a range of pathologies. It is now believed, however, that at basal levels these molecules also have a beneficial cellular function in the form of cell signaling and redox regulation. Critical to elucidating their physiological role is the opportunity to visualize and quantify the production of ROS with spatiotemporal accuracy. Armed with a newly developed, extremely sensitive fluorogenic α-tocopherol analogue (HBPMHC), we report herein the observation of steady concentrations of lipid peroxyl radicals produced in live cell imaging conditions. Imaging studies with HBPMHC indicate that the rate of production of lipid peroxyl radicals in HeLa cells under basal conditions is 33 nM/h within the cell. Our work further provides indisputable evidence on the antioxidant role of Vitamin E, as lipid peroxidation was suppressed in HeLa cells both under basal conditions and in the presence of Haber-Weiss chemistry, generated by the presence of cumyl hydroperoxide and Cu in solution, when supplemented with the α-tocopherol surrogate, PMHC (2,2,5,7,8-pentamethyl-6-hydroxy-chromanol, an α-tocopherol analogue lacking the phytyl tail). HBPMHC has the sensitivity needed to detect trace changes in oxidative status within the lipid membrane, underscoring the opportunity to illuminate the physiological relevance of lipid peroxyl radical production during cell homeostasis and disease.

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Section: Resultssupporting

confidence: 94%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Rate of Lipid Peroxyl Radical Production during Cellular Homeostasis Unraveled via Fluorescence Imaging

2017

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“…Subsequently, the disaggregated BODIPY residues can interact with the hydrophobic BSA pocket to form dye–protein complexes (Figure c). The hydrophobic dye–protein interaction significantly decreases the polarity of the dye’s microenvironment and reduces the rotations around single bonds in the meso position. − …”

Section: Resultsmentioning

confidence: 99%

Redox-Activated Light-Up Nanomicelle for Precise Imaging-Guided Cancer Therapy and Real-Time Pharmacokinetic Monitoring

Liu

et al. 2016

ACS Nano

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Simultaneous tumor imaging, therapy, and pharmacokinetic monitoring can offer a safe and effective strategy for cancer therapy. This work describes the design of a fluorescence light-up nanomicelle that can afford precise imaging-guided drug delivery and pharmacokinetic monitoring in a real-time fashion for cancer chemotherapy. The nanomicelle, which contains a boron dipyrromethene based fluorescent probe as the hydrophobic core and a redox-triggered detachable poly(ethylene glycol) (PEG) shell, can accumulate at the tumor site via enhanced permeation and retention effect. The PEG detachment induced by tumoral and intracellular glutathione can destabilize the nanomicelle, leading to fluorescence light up and simultaneous drug release. Importantly, the fluorescence intensities generated by the nanomicelles in different organs are well-correlated with released drug concentrations in both temporal and spatial manners, suggesting its precise role for imaging-guided drug delivery and pharmacokinetic monitoring in vivo. The tumor growth can be effectively inhibited by the docetaxel-loaded nanomicelle formulation, and the nanomicelles are monitored to be excreted via hepatobiliary routes. This nanomicelle for precise imaging-guided chemotherapy provides a safe and robust theranostic strategy for the evaluation of cancer nanomedicine.

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“…[13][14] Several fluorescent dyes are already known for SA binding, but the binding site and stoichiometry is not explored in most of the cases. [14][15][16][17] Quite a few numbers of fluorescent probes have been developed based on their sensitivity towards local polarity and viscosity, which causes a significant change in emissive states upon binding to the multiple hydrophobic pockets present in SA. 18 Nevertheless, limitations arise due to the absorbance of the probes in the near-UV region resulting to the interference by the auto-fluorescence of protein molecules, change in the secondary structure of protein upon ligand binding and lower selectivity of the sensor while other relevant analytes are present.…”

mentioning

confidence: 99%

Cellular metabolic activity marker via selective turn-ON detection of serum albumin using an NBD-based fluoroprobe

Dutta¹,

Pal²,

Koner³

2019

Preprint

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A nitrobenzoxadiazole-based fluoroprobe (NBD-Bu) is designed to probe cellular metabolic activity in cancer and normal cells. NBD-Bu shows a significant fluorescence enhancement upon selective binding to serum albumin. The site specificity of NBD-Bu has been explored through a competitive displacement assay in the presence of site-specific markers such as warfarin and ibuprofen. Subsequently, high-resolution fluorescence microscopy results consolidated the potential of NBD-Bu for cellular imaging and detection of abnormal cellular metabolic activity.

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Interaction of BODIPY dyes with bovine serum albumin: a case study on the aggregation of a click-BODIPY dye

Cited by 38 publications

References 20 publications

Rate of Lipid Peroxyl Radical Production during Cellular Homeostasis Unraveled via Fluorescence Imaging

Rate of Lipid Peroxyl Radical Production during Cellular Homeostasis Unraveled via Fluorescence Imaging

Redox-Activated Light-Up Nanomicelle for Precise Imaging-Guided Cancer Therapy and Real-Time Pharmacokinetic Monitoring

Cellular metabolic activity marker via selective turn-ON detection of serum albumin using an NBD-based fluoroprobe

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