scholarly journals Semi-Quantitatively Designing Two-Photon High-Performance Fluorescent Probes for Glutathione S-Transferases

Research ◽  
2020 ◽  
Vol 2020 ◽  
pp. 1-11
Author(s):  
Xue-Xiang Zhang ◽  
Huan Qi ◽  
Mei-Heng Lu ◽  
Song-Qiu Yang ◽  
Peng Li ◽  
...  
Keyword(s):  
Fluorescent Probes ◽  
High Performance ◽  
Density Functional ◽  
Transient Absorption ◽  
Theoretical Calculations ◽  
Detoxification Enzymes ◽  
Live Cells ◽  
Conceptual Density Functional Theory ◽  
Two Photon ◽  
Glutathione S Transferases

Glutathione S-transferases (GSTs), detoxification enzymes that catalyze the addition of glutathione (GSH) to diverse electrophilic molecules, are often overexpressed in various tumor cells. While fluorescent probes for GSTs have often adopted the 2,4-dinitrobenzenesulfonyl (DNs) group as the receptor unit, they usually suffer from considerable background reaction noise with GSH due to excessive electron deficiency. However, weakening this reactivity is generally accompanied by loss of sensitivity for GSTs, and therefore, finely turning down the reactivity while maintaining certain sensitivity is critical for developing a practical probe. Here, we report a rational semiquantitative strategy for designing such a practical two-photon probe by introducing a parameter adopted from the conceptual density functional theory (CDFT), the local electrophilicity ωk, to characterize this reactivity. As expected, kinetic studies established ωk as efficient to predict the reactivity with GSH, and probe NI3 showing the best performance was successfully applied to detecting GST activities in live cells and tissue sections with high sensitivity and signal-to-noise ratio. Photoinduced electron transfer of naphthalimide-based probes, captured by femtosecond transient absorption for the first time and unraveled by theoretical calculations, also contributes to the negligible background noise.

Benzimidazole-Based Ratiometric Two-Photon Fluorescent Probes for Acidic pH in Live Cells and Tissues

2013 ◽  
Vol 135 (47) ◽  
pp. 17969-17977 ◽  
Author(s):  
Hyung Joong Kim ◽  
Cheol Ho Heo ◽  
Hwan Myung Kim
Keyword(s):  
Fluorescent Probes ◽  
Live Cells ◽  
Acidic Ph ◽  
Two Photon

Lysosome-targeted two-photon fluorescent probes for rapid detection of H2S in live cells

2019 ◽  
Vol 43 (3) ◽  
pp. 1267-1274 ◽  
Author(s):  
Gongchun Li ◽  
Saige Ma ◽  
Jun Tang ◽  
Yong Ye
Keyword(s):  
Fluorescent Probes ◽  
Rapid Detection ◽  
High Sensitivity ◽  
Live Cells ◽  
Two Photon

Two novel two-photon fluorescent probes (BHNP-DA and M2) were designed and synthesized and show good selectivity and high sensitivity to H2S.

Dual-color imaging of cytosolic and mitochondrial zinc ions in live tissues with two-photon fluorescent probes

2014 ◽  
Vol 12 (21) ◽  
pp. 3406-3412 ◽  
Author(s):  
Kailash Rathore ◽  
Chang Su Lim ◽  
Young Lee ◽  
Bong Rae Cho
Keyword(s):  
Fluorescent Probes ◽  
Live Cells ◽  
Zinc Ions ◽  
Color Imaging ◽  
Two Photon ◽  
Dual Color ◽  
Living Tissues

We have developed TP probes for [Zn2+]cyto and [Zn2+]mito, which emit TPEF at widely-separated wavelength regions. The new probes can simultaneously detect [Zn2+]cyto and [Zn2+]mito in live cells, as well as in living tissues by dual-color TPM imaging.

scholarly journals The Synthesis and Photophysical Properties of Weakly Coupled Diketopyrrolopyrroles

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4744
Author(s):  
Michał Pieczykolan ◽  
James B. Derr ◽  
Amara Chrayteh ◽  
Beata Koszarna ◽  
John A. Clark ◽  
...  
Keyword(s):  
Excited States ◽  
Density Functional ◽  
Transient Absorption ◽  
Theoretical Calculations ◽  
Photophysical Properties ◽  
Electronic Transitions ◽  
Intersystem Crossing ◽  
Straightforward Manner ◽  
Functional Theory ◽  
Weakly Coupled

Three centrosymmetric diketopyrrolopyrroles possessing either two 2-(2′-methoxyphenyl)benzothiazole or two 2-(2′-methoxyphenyl)benzoxazolo-thiophene scaffolds were synthesized in a straightforward manner, and their photophysical properties were investigated. Their emission was significantly bathochromically shifted as compared with that of simple DPPs reaching 650 nm. Judging from theoretical calculations performed with time-dependent density functional theory, in all three cases the excited state was localized on the DPP core and there was no significant CT character. Consequently, emission was almost independent of solvents’ polarity. DPPs possessing 2,5-thiophene units vicinal to DPP core play a role in electronic transitions, resulting in bathochromically shifted absorption and emission. Interestingly, as judged from transient absorption dynamics, intersystem crossing was responsible for the deactivation of the excited states of DPPs possessing para linkers but not in the case of dye bearing meta linker.

scholarly journals A synergistic strategy to develop photostable and bright dyes with long Stokes shift for super-resolution microscopy

2021 ◽  
Author(s):  
gangwei jiang ◽  
Tian-Bing Ren ◽  
Elisa D’Este ◽  
mengyi xiong ◽  
Bin Xiong ◽  
...  
Keyword(s):  
Fluorescent Probes ◽  
Stokes Shift ◽  
Super Resolution ◽  
Stimulated Emission ◽  
Live Cells ◽  
Sted Microscopy ◽  
New Class ◽  
Two Photon ◽  
Cellular Environment ◽  
Super Resolution Microscopy

Abstract The quality and application of super-resolution fluorescence imaging greatly lie in the properties of fluorescent probes. However, conventional fluorophores in a cellular environment often suffer from low brightness, poor photostability, and short Stokes shift (< 30 nm). Here we report a synergistic strategy to simultaneously improve such properties of regular fluorophores. Introduction of quinoxaline motif with fine-tuned electron density to conventional rhodamines generates new dyes with vibronic structure and inhibited twisted-intramolecular-charge-transfer (TICT) formation synchronously, thus increasing the brightness and photostability as well as Stokes shift. The new fluorophore BDQF-6 exhibits around twofold greater brightness (ε × Φ = 6.6 × 104 L·mol− 1·cm− 1) and Stokes shift (56 nm) than its parental fluorophore, Rhodamine B. Importantly, in Stimulated Emission Depletion (STED) microscopy, BDQF-6 derived probe possesses a superior photostability and thus renders threefold more frames than carbopyronine- and JF608-based probes, known as photostable fluorophores for STED imaging. More BDQF-6 derivatives were developed next, allowing us to perform wash-free organelles (mitochondria and lysosome) staining and protein labeling with ultrahigh signal-to-noise ratios (up to 106 folds) in confocal and STED microscopy of live cells, or two-photon and 3D STED microscopy of fixed cells. Furthermore, the strategy was well generalized to different types of dyes (pyronin, rhodol, coumarin, and Boranil), offering a new class of bright and photostable fluorescent probes with long Stokes shift (up to 136 nm) for bioimaging and biosensing.

Two-Photon Fluorescent Probes for Acidic Vesicles in Live Cells and Tissue

2008 ◽  
Vol 120 (12) ◽  
pp. 2263-2266 ◽  
Author(s):  
Hwan Myung Kim ◽  
Myoung Jin An ◽  
Jin Hee Hong ◽  
Byeong Ha Jeong ◽  
Ohyun Kwon ◽  
...  
Keyword(s):  
Fluorescent Probes ◽  
Live Cells ◽  
Two Photon ◽  
Acidic Vesicles

Targetable, two-photon fluorescent probes for local nitric oxide capture in the plasma membranes of live cells and brain tissues

The Analyst ◽  
2018 ◽  
Vol 143 (17) ◽  
pp. 4180-4188 ◽  
Author(s):  
Xinfu Zhang ◽  
Benlei Wang ◽  
Yi Xiao ◽  
Chao Wang ◽  
Ling He
Keyword(s):  
Nitric Oxide ◽  
Plasma Membrane ◽  
Fluorescent Probe ◽  
Fluorescent Probes ◽  
Plasma Membranes ◽  
Live Cells ◽  
Two Photon ◽  
In Cells ◽  
Brain Tissues

A plasma membrane-targetable two-photon fluorescent probe for capturing nitric oxide in cells and brain tissues.

scholarly journals Diketopyrrolopyrrole based highly conjugated small molecules for organic solar cells

2021 ◽  
Vol 5 (1) ◽  
Author(s):  
Sana Akram ◽  
Azra Quraishi ◽  
Abid Hussain ◽  
Nadia Zulfiqar ◽  
Madiha Akbar
Keyword(s):  
Small Molecules ◽  
Organic Solar Cells ◽  
Organic Solar Cell ◽  
High Performance ◽  
Density Functional ◽  
Theoretical Calculations ◽  
Functional Theory ◽  
Donor And Acceptor ◽  
Td Dft ◽  
Optimization Of Geometry

A series of three donor molecules (DPP-B, DPP-N and DPP-P) based on diketopyrrolopyrrole (DPP) sharing the similar backbone of D-π-A-π-D have been investigated. In these molecules, substituents such as pyrene, naphthalene and benzene act as the electron donating end groups, DPP as the central core unit and thiophene has been used as a bridge between donor and acceptor fragments. Theoretical calculations have been carried out with the help of density functional theory (DFT) and time-dependent functional theory (TD-DFT). For the optimization of geometry of investigated molecules, DFT functional B3LYP/6-31g(d) has been used and TD-B3LYP/6-31g(d) has been used to obtain the best results of calculations inexcited state. DPP-P has been considered a suitable donor molecule among all investigated molecules as it manifests the suitable value of Eg of 2.24 eV and showed the stronger absorption λmaxof 611 nm. Hence, this study reveals that investigated donor molecules are suitable for high performance organic solar cell devices

Two-Photon Fluorescent Probes for Acidic Vesicles in Live Cells and Tissue

2008 ◽  
Vol 47 (12) ◽  
pp. 2231-2234 ◽  
Author(s):  
Hwan Myung Kim ◽  
Myoung Jin An ◽  
Jin Hee Hong ◽  
Byeong Ha Jeong ◽  
Ohyun Kwon ◽  
...  
Keyword(s):  
Fluorescent Probes ◽  
Live Cells ◽  
Two Photon ◽  
Acidic Vesicles

Thymine Dimerization Induced by Oxidative DNA Lesions and Epigenetic Intermediates via Triplet-Triplet Energy Transfer

2020 ◽  
Author(s):  
Mauricio Lineros-Rosa ◽  
Antonio Francés-Monerris ◽  
Antonio Monari ◽  
Miguel Angél Miranda ◽  
Virginie Lhiaubet-Vallet
Keyword(s):  
Energy Transfer ◽  
Excitation Energy ◽  
Transient Absorption ◽  
Theoretical Calculations ◽  
Dna Lesions ◽  
Transient Absorption Spectroscopy ◽  
Triplet Energy ◽  
Pyrimidine Dimers ◽  
Triplet Energy Transfer ◽  
Dna Nucleobases

Interaction of nucleic acids with light is a scientific question of paramount relevance not only in the understanding of life functioning and evolution, but also in the insurgence of diseases such as malignant skin cancer and in the development of biomarkers and novel light-assisted therapeutic tools. This work shows that the UVA portion of sunlight, not absorbed by canonical DNA nucleobases, can be absorbed by 5-formyluracil (ForU) and 5-formylcytosine (ForC), two ubiquitous oxidative lesions and epigenetic intermediates present in living beings in natural conditions. We measure the strong propensity of these molecules to populate triplet excited states able to transfer the excitation energy to thymine-thymine dyads, inducing the formation of the highly toxic and mutagenic cyclobutane pyrimidine dimers (CPDs). By using steady-state and transient absorption spectroscopy, NMR, HPLC, and theoretical calculations, we quantify the differences in the triplet-triplet energy transfer mediated by ForU and ForC, revealing that the former is much more efficient in delivering the excitation energy and producing the CPD photoproduct. Although significantly slower than ForU, ForC is also able to harm DNA nucleobases and therefore this process has to be taken into account as a viable photosensitization mechanism. The present findings evidence a rich photochemistry crucial to understand DNA photodamage and of potential use in the development of biomarkers and non-conventional photodynamic therapy agents.

Sign in / Sign up

Export Citation Format

Share Document