Solid-phase synthesis of BODIPY dyes and development of an immunoglobulin fluorescent sensor

Vendrell, Marc; Krishna, G. Gopi; Ghosh, Krishna; Zhai, Duanting; Lee, Jung Hoon; Zhu, Qing; Yau, Yin Hoe; Shochat, Susana Geifman; Kim, Hyori; Chung, Jaeyoung; Chang, Young‐Tae

doi:10.1039/c1cc11774b

Cited by 59 publications

(44 citation statements)

References 36 publications

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“…For independent analysis of NP circulation, a separate batch of nanoparticles labeled with a BODIPY emitting in the green channel were prepared by conjugating 10-(2-aminoethyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo{1,2-c:2’,1’-f}{1,3,2}diazaborinin-4-ium-5-uide hydrochloride [synthesized by adapting a known method (37)] to PLGA using the methods described for the case of the PLGA-BODIPY630. Loadings were determined as described above (ex/em 483/525 nm).…”

Section: Methodsmentioning

confidence: 99%

Single-cell pharmacokinetic imaging reveals a therapeutic strategy to overcome drug resistance to the microtubule inhibitor eribulin

et al. 2014

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Eribulin mesylate was developed as a potent microtubule-targeting cytotoxic agent to treat taxane-resistant cancers, but recent clinical trials have shown that it eventually fails in many patient sub-populations for unclear reasons. To investigate its resistance mechanisms, we developed a fluorescent analog of eribulin with pharmacokinetic (PK) properties and cytotoxic activity across a human cell line panel that are sufficiently similar to the parent drug to study its cellular PK and tissue distribution. Using intravital imaging and automated tracking of cellular dynamics, we found that resistance to eribulin and the fluorescent analog depended directly on the multidrug resistance protein 1 (MDR1). Intravital imaging allowed for real-time analysis of in vivo pharmacokinetics in tumors that were engineered to be spatially heterogeneous for taxane resistance, whereby an MDR1-mApple fusion protein distinguished resistant cells fluorescently. In vivo, MDR1-mediated drug efflux and the three-dimensional tumor vascular architecture were discovered to be critical determinants of drug accumulation in tumor cells. We furthermore show that standard intravenous administration of a third-generation MDR1 inhibitor, HM30181, failed to rescue drug accumulation; however, the same MDR1 inhibitor encapsulated within a nanoparticle delivery system reversed the multidrug-resistant phenotype and potentiated the eribulin effect in vitro and in vivo in mice. Our work demonstrates that in vivo assessment of cellular PK of an anticancer drug is a powerful strategy for elucidating mechanisms of drug resistance in heterogeneous tumors and evaluating strategies to overcome this resistance.

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Section: Methodsmentioning

confidence: 99%

Single-cell pharmacokinetic imaging reveals a therapeutic strategy to overcome drug resistance to the microtubule inhibitor eribulin

et al. 2014

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“…1) have emerged as a fascinating class of dyes with excellent performance and stability. Thereby, these compounds have found application in sensing, labelling, light-harvesting technologies and photodynamic therapy [2][3][4][5][6][7][8][9][10][11]. For a long time it was considered that homoleptic dipyrrinato metal complexes were incapable to fluorescence, in contrast to their highly fluorescent boron-dipyrrinato analogues.…”

Section: Introductionmentioning

confidence: 98%

New luminophors based on the binuclear helicates of d-METALS with BIS(DIPYRRIN)S

et al. 2015

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“…Furthermore, the BODIPY scaffold is particularly advantageous for novel fluorophore development since small modifications to its structure enables tuning of its fluorescence characteristics and the scaffold can be readily customized using a variety of synthetic routes 8–14 . Fluorophore libraries originating from various core BODIPY scaffolds have resulted in probes with an array of Stokes shifts which have demonstrated utility as chemical sensors and probes 15–18 . However, the previously synthesized BODIPY fluorophore libraries did not contain chemical moieties suitable for conjugation chemistries, limiting their utility for affinity tag labeling.…”

Section: Introductionmentioning

confidence: 99%

Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy

Bittel

Davis

Wang

et al. 2018

Sci Rep

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Multicolor microscopy tools necessary to localize and visualize the complexity of subcellular systems are limited by current fluorophore technology. While commercial fluorophores cover spectral space from the ultraviolet to the near infrared region and are optimized for conventional bandpass based fluorescence microscopy, they are not ideal for highly multiplexed fluorescence microscopy as they tend to have short Stokes shifts, restricting the number of fluorophores that can be detected in a single sample to four to five. Herein, we synthesized a library of 95 novel boron-dipyrromethene (BODIPY)-based fluorophores and screened their photophysical, optical and spectral properties for their utility in multicolor microscopy. A subset of our BODIPY-based fluorophores yielded varied length Stokes shifts probes, which were used to create a five-color image using a single excitation with confocal laser scanning microscopy for the first time. Combining these novel fluorophores with conventional fluorophores could facilitate imaging in up to nine to ten colors using linear unmixing based microscopy approaches.

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Solid-phase synthesis of BODIPY dyes and development of an immunoglobulin fluorescent sensor

Cited by 59 publications

References 36 publications

Single-cell pharmacokinetic imaging reveals a therapeutic strategy to overcome drug resistance to the microtubule inhibitor eribulin

Single-cell pharmacokinetic imaging reveals a therapeutic strategy to overcome drug resistance to the microtubule inhibitor eribulin

New luminophors based on the binuclear helicates of d-METALS with BIS(DIPYRRIN)S

Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy

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