Fluorescence emission originated from the H-aggregated cyanine dye with chiral gemini surfactant assemblies having a narrow absorption band and a remarkably large Stokes shift

Ryu, Naoya; Okazaki, Yutaka; Pouget, Émilie; Takafuji, Makoto; Nagaoka, Shoji; Ihara, Hirotaka; Oda, Reïko

doi:10.1039/c7cc04484d

Cited by 57 publications

(49 citation statements)

References 33 publications

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“…To assess overall solubility, we took advantage of the fact that dye labeled molecules change both in intensity and excitation maxima depending on solubility and aggregation. This aggregation behavior has been described for cyanine dyes and likely further reduces availability in aqueous buffers . We therefore measured absorption of the probes over a range of wavelengths near their absorption maximum of 650 nm.…”

Section: Resultsmentioning

confidence: 89%

Design of Optical‐Imaging Probes by Screening of Diverse Substrate Libraries Directly in Disease‐Tissue Extracts

et al. 2020

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Fluorescently quenched probes that are specifically activated in the cancer microenvironment have great potential application for diagnosis,e arly detection, and surgical guidance.T hese probes are often designed to target specific enzymes associated with diseases by direct optimization using single purified enzymes.However,this can result in painstaking chemistry efforts to produce ap robe with suboptimal performance when applied in vivo.W ed escribe here an alternate, unbiased activity-profiling approach in whichw hole tissue extracts are used to directly identify optimal peptide sequences for probe design. Screening of tumor extracts with ah ybrid combinatorial substrate library (HyCoSuL) identified ac ombination of natural and non-natural amino-acid residues that was used to generate highly efficient tumor-specific probes. This new strategy simplifies and enhances the process of probe optimization without any apriori knowledge of enzyme targets and has the potential to be applied to diverse disease states using clinical or animal-model tissue samples.

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Section: Resultsmentioning

confidence: 89%

Design of Optical‐Imaging Probes by Screening of Diverse Substrate Libraries Directly in Disease‐Tissue Extracts

et al. 2020

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“…To assess overall solubility, we took advantage of the fact that dye labeled molecules change both in intensity and excitation maxima depending on solubility and aggregation. This aggregation behavior has been described for cyanine dyes and likely further reduces availability in aqueous buffers [29]. We therefore measured absorption of the probes over a range of wavelengths near their absorption maximum of 650 nm.…”

Section: Performance Of Probes In Cells Depends On Permeability and Smentioning

confidence: 81%

Design of optical imaging probes by screening of diverse substrate libraries directly in disease tissue extracts

Tholen

Yim

Groborz

et al. 2020

Preprint

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Fluorescently-quenched probes that are specifically activated in the cancer microenvironment have great potential application for diagnosis, early detection and surgical guidance. These probes are often designed to target specific enzymes associated with disease by direct optimization using single purified targets. However, this can result in painstaking chemistry efforts to produce a probe with suboptimal performance when applied in vivo. We describe here an alternate, unbiased activity-profiling approach in which whole tissue extracts are used to directly identify optimal peptide sequences for probe design. Screening of mouse mammary tumor extracts with a hybrid combinatorial substrate library (HyCoSuL) identified a combination of natural and non-natural amino acid residues that could be used to generate highly efficient tumorspecific fluorescently quenched substrate probes. The most effective probe is significantly brighter than any of our previously reported tumor imaging probes designed for specific proteases and robustly discriminates tumor tissue from adjacent healthy tissue in a mouse model of cancer.Importantly, although the probes were developed by screening mouse mammary tumor tissues, they are able to effectively distinguish human ductal carcinomas from normal breast tissue with similar reactivity profiles to those observed in mouse tissues. This new strategy simplifies and enhances the process of probe optimization by direct screening in a tissue of interest without any a priori knowledge of enzyme targets. It has the potential to be applied to advance the development of probes for diverse disease states for which clinical or animal model tissues are available.3

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“…Cyanine dye structure and environment play an important function in the assembly and disassembly of dyes [26]. Some cyanine dyes are able to form H-aggregates or J-aggregates in special environments [27,28]. As shown in Figure 2, dimeric cyanine dyes (TC-P3-6) can form a mixture of dimer (550 nm) and monomer (586 nm) in DMSO, and mixture aggregates or H-aggregates (492 nm) in PBS with similar compounds [17,29,30] and an exciton model [31].…”

Section: Resultsmentioning

confidence: 99%

Disassembly of Dimeric Cyanine Dye Supramolecular Assembly by Tetramolecular G-quadruplex Dependence on Linker Length and Layers of G-quartet

Yu¹,

Zhang²,

Ding³

et al. 2019

Molecules

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Cyanine dyes have been widely applied in various biological systems owing to their specific photochemical properties. Assembly and disassembly process of cyanine dyes were constructed and regulated by special biomolecules. In this paper, dimeric cyanine dyes with different repeat units (oligo-oxyethylene) in linker (TC-Pn) (n = 3–6) were found to form H-aggregates or mixture aggregates in PBS. These aggregates could be disassembled into dimer and/or monomer by (TGnT) tetramolecular G-quadruplexes (n = 3–6, 8), which were affected by the linker length of dimeric cyanine dyes and layers of G-quartets. The 1H-NMR titration results suggest that the binding mode of dimeric cyanine dye with TGnT might be on both ends—stacking like a clip. This binding mode could clearly explain that matching structures between dimeric cyanine dyes and TGnT quadruplexes could regulate the disassembly properties of aggregates. These results could provide clues for the development of highly specific G-quadruplex probes.

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Fluorescence emission originated from the H-aggregated cyanine dye with chiral gemini surfactant assemblies having a narrow absorption band and a remarkably large Stokes shift

Cited by 57 publications

References 33 publications

Design of Optical‐Imaging Probes by Screening of Diverse Substrate Libraries Directly in Disease‐Tissue Extracts

Design of Optical‐Imaging Probes by Screening of Diverse Substrate Libraries Directly in Disease‐Tissue Extracts

Design of optical imaging probes by screening of diverse substrate libraries directly in disease tissue extracts

Disassembly of Dimeric Cyanine Dye Supramolecular Assembly by Tetramolecular G-quadruplex Dependence on Linker Length and Layers of G-quartet

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