Hydrogen bond strengthening induces fluorescence quenching of PRODAN derivative by turning on twisted intramolecular charge transfer

Yang, Yonggang; Li, Donglin; Li, Chaozheng; Liu, YuFang; Jiang, Kai

doi:10.1016/j.saa.2017.06.029

Cited by 28 publications

(9 citation statements)

References 59 publications

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“…Polar solvents stabilize this excited state leading to a red-shift in emission. Hydrogen bonding in protic solvents has also been shown to contribute to the observed red-shift by enhancing the intramolecular charge transfer. , Compared to Prodan, Anap has an additional amino acid functionality (Figure A, inset), which allows for incorporation into protein; however, this is structurally well-separated from the amine and carbonyl groups and the aromatic core, and thus is not expected to alter the underlying photophysics substantially compared to Prodan. The observed emission maximum wavelengths for Anap are consistent with this, red-shifting substantially with increasing solvent polarity (ε s ) and with the protic alcohols showing greater red-shifting than the aprotic, yet more polar solvent, DMSO.…”

Section: Resultsmentioning

confidence: 67%

Wavelength-Dependent Fluorescent Immunosensors via Incorporation of Polarity Indicators near the Binding Interface of Antibody Fragments

et al. 2019

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Herein, we describe a fluorescent immunosensor designed by incorporating an unnatural amino acid fluorophore into the binding site of an EGFR-specific antibody fragment, resulting in quantifiable EGFR-dependent changes in peak fluorescence emission wavelength. To date, immunosensor design strategies have relied on binding-induced changes in fluorescence intensity that are prone to excitation source fluctuations and sample-dependent noise. In this study, we used a rational design approach to incorporate a polarity indicator (Anap) into specific positions of an anti-EGFR single chain antibody to generate an emission wavelength-dependent immunosensor. We found that when incorporated within the topological neighborhood of the antigen binding interface, the Anap emission wavelength is blue-shifted by EGFR-binding in a titratable manner, up to 20 nm, with nanomolar detection limits. This approach could be applicable to other antibody/antigen combinations for integration into a wide range of assay platforms (including homogeneous, solid-phase assay, or microfluidic assays) for one-step protein quantification.

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Section: Resultsmentioning

confidence: 67%

Wavelength-Dependent Fluorescent Immunosensors via Incorporation of Polarity Indicators near the Binding Interface of Antibody Fragments

et al. 2019

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“…[7] Redshift is due to matching alignment between the molecules and the solvent that lowers the HOMO-LUMO gap. [8] Quenching is more complicated and influenced by many factors.F or instance,t wisted intramolecular charge transfer (TICT) dissipates the excitation energy through bond rotation ( Figure 1A). [9] In accord with the "energy gap law" energy is released through electron transition from excited states to the empty orbitals.…”

mentioning

confidence: 99%

Enhancing the Anti‐Solvatochromic Two‐Photon Fluorescence for Cirrhosis Imaging by Forming a Hydrogen‐Bond Network

et al. 2018

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Two-photon imaging is an emerging tool for biomedical research and clinical diagnostics. Electron donor-acceptor (D-A) type molecules are the most widely employed two-photon scaffolds. However, current D-A type fluorophores suffer from solvatochromic quenching in aqueous biological samples. To address this issue, we devised a novel class of D-A type green fluorescent protein (GFP) chromophore analogues that form a hydrogen-bond network in water to improve the two-photon efficiency. Our design results in two-photon chalcone (TPC) dyes with 0.80 quantum yield and large two-photon action cross section (210 GM) in water. This strategy to form hydrogen bonds can be generalized to design two-photon materials with anti-solvatochromic fluorescence. To demonstrate the improved in vivo imaging, we designed a sulfide probe based on TPC dyes and monitored endogenous H S generation and scavenging in the cirrhotic rat liver for the first time.

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“…As shown in Figure 2b, the PL spectra of R6G-loaded BU-PEG nanogels containing 13% and 19% R6G (weight ratios of 1:1 and 0.5:1, respectively) in water exhibited maximum fluorescence peaks at 555 nm with the same intensity of around 1300, possibly due to the presence of the similar DLC of the nanogels. Interestingly, the maximum PL fluorescence peaks and intensities of the A-R6G-loaded BU-PEG nanogels with various DLC values were remarkably different to those of the R6G-loaded BU-PEG system: the A-R6G-loaded nanogels exhibited a significant blue-shift in their maximum fluorescence peaks from 555 nm to 549 nm, and a gradual increase in the maximum fluorescence intensity from 2740 to 3980 as the DLC increased, suggesting that the physical encapsulation of the A-R6G in the nanogels through complementary A-U interactions efficiently prevented the aggregation of the polycyclic aromatic rings of A-R6G within the nanogels [39,40], resulting in a significant blue-shift of the maximum fluorescence peak and a progressive enhancement in fluorescence intensity with the DLC, even with A-R6G-loading contents as high as 51%. Thus, these findings further demonstrate that the A-U interactions within this complementary drug-nanocarrier system manipulate the drug-encapsulation and fluorescence behavior of the nanogels in aqueous environments.…”

Section: Resultsmentioning

confidence: 98%

Complementary Nucleobase Interactions Drive Co-Assembly of Drugs and Nanocarriers for Selective Cancer Chemotherapy

2021

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A new concept in cooperative adenine–uracil (A–U) hydrogen bonding interactions between anticancer drugs and nanocarrier complexes was successfully demonstrated by invoking the co-assembly of water soluble, uracil end-capped polyethylene glycol polymer (BU-PEG) upon association with the hydrophobic drug adenine-modified rhodamine (A-R6G). This concept holds promise as a smart and versatile drug delivery system for the achievement of targeted, more efficient cancer chemotherapy. Due to A–U base pairing between BU-PEG and A-R6G, BU-PEG has high tendency to interact with A-R6G, which leads to the formation of self-assembled A-R6G/BU-PEG nanogels in aqueous solution. The resulting nanogels exhibit a number of unique physical properties, including extremely high A-R6G-loading capacity, well-controlled, pH-triggered A-R6G release behavior, and excellent structural stability in biological media. Importantly, a series of in vitro cellular experiments clearly demonstrated that A-R6G/BU-PEG nanogels improved the selective uptake of A-R6G by cancer cells via endocytosis and promoted the intracellular release of A-R6G to subsequently induce apoptotic cell death, while control rhodamine/BU-PEG nanogels did not exert selective toxicity in cancer or normal cell lines. Overall, these results indicate that cooperative A–U base pairing within nanogels is a critical factor that improves selective drug uptake and effectively promotes apoptotic programmed cell death in cancer cells.

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Hydrogen bond strengthening induces fluorescence quenching of PRODAN derivative by turning on twisted intramolecular charge transfer

Cited by 28 publications

References 59 publications

Wavelength-Dependent Fluorescent Immunosensors via Incorporation of Polarity Indicators near the Binding Interface of Antibody Fragments

Wavelength-Dependent Fluorescent Immunosensors via Incorporation of Polarity Indicators near the Binding Interface of Antibody Fragments

Enhancing the Anti‐Solvatochromic Two‐Photon Fluorescence for Cirrhosis Imaging by Forming a Hydrogen‐Bond Network

Complementary Nucleobase Interactions Drive Co-Assembly of Drugs and Nanocarriers for Selective Cancer Chemotherapy

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