Design of Large Stokes Shift Fluorescent Proteins Based on Excited State Proton Transfer of an Engineered Photobase

2021 ◽  
Vol 143 (37) ◽  
pp. 15091-15102
Author(s):  
Elizabeth M. Santos ◽  
Wei Sheng ◽  
Rahele Esmatpour Salmani ◽  
Setare Tahmasebi Nick ◽  
Alireza Ghanbarpour ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Proteins ◽  
Stokes Shift ◽  
Large Stokes Shift ◽  
Excited State Proton Transfer

Sibling rivalry: intrinsic luminescence from two xanthene dye monoanions, resorufin and fluorescein, provides evidence for excited-state proton transfer in the latter

2017 ◽  
Vol 19 (36) ◽  
pp. 24440-24444 ◽  
Author(s):  
Christina Kjær ◽  
Steen Brøndsted Nielsen ◽  
Mark H. Stockett
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Gas Phase ◽  
Emission Band ◽  
Stokes Shift ◽  
Sibling Rivalry ◽  
Core Structure ◽  
Intrinsic Luminescence ◽  
Large Stokes Shift ◽  
Excited State Proton Transfer

Excited-state proton transfer in gas-phase fluorescein monoanions results in a broad, featureless emission band and a large Stokes shift compared to resorufin, which shares the same xanthene core structure.

Against the NEER principle: The third type of photochromism for GFP chromophore derivatives

2021 ◽  
Author(s):  
Jun-Wei Liao ◽  
Robert Sung ◽  
Kuangsen Sung
Keyword(s):  
Excited State ◽  
Green Fluorescent Protein ◽  
Proton Transfer ◽  
Fluorescent Protein ◽  
Fluorescent Proteins ◽  
The Third ◽  
Excited State Proton Transfer ◽  
Gfp Chromophore ◽  
Green Fluorescent

Photochromism is the heart of photochromic fluorescent proteins. Excited-state proton transfer (ESPT) is the major photochromism for green fluorescent protein (GFP) and Z-E photoisomerization through τ-torsion is the major photochromism...

scholarly journals An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer

2017 ◽  
Vol 53 (26) ◽  
pp. 3697-3700 ◽  
Author(s):  
Dipendra Dahal ◽  
Lucas McDonald ◽  
Xiaoman Bi ◽  
Chathura Abeywickrama ◽  
Farai Gombedza ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Stokes Shift ◽  
Intramolecular Proton Transfer ◽  
Large Stokes Shift

A NIR-emitting probe with a large Stokes shift (Δλ ≈ 234 nm) can selectively show lysosome organelles without exhibiting “an alkalinizing effect”.

Excited-State Proton Transfer in Fluorescent Photoactive Yellow Protein Containing 7-Hydroxycoumarin

2014 ◽  
Vol 896 ◽  
pp. 85-88
Author(s):  
Dian Novitasari ◽  
Hironari Kamikubo ◽  
Yoichi Yamazaki ◽  
Mariko Yamaguchi ◽  
Mikio Kataoka
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Fluorescent Protein ◽  
Stokes Shift ◽  
Spectroscopic Studies ◽  
Photoactive Yellow Protein ◽  
Excited State Proton Transfer ◽  
Hydrogen Bonding Network ◽  
Green Fluorescent

Green fluorescent protein (GFP) has been used as an effective tool in various biological fields. The large Stokes shift resulting from an excited-state proton transfer (ESPT) is the basis for the application of GFP in such techniques as ratiometric GFP biosensors. The chromophore of GFP is known to be involved in a hydrogen-bonding network. Previous X-ray crystallographic and FTIR studies suggest that a proton wire along the hydrogen-bonding network plays a role in the ESPT. In order to examine the relationship between the ESPT and hydrogen-bonding network within proteins, we prepared an artificial fluorescent protein using a light-sensor protein, photoactive yellow protein (PYP). The native chromophore of p-coumaric acid (pCA) of PYP undergoes trans-cis isomerization after absorbing a photon, which triggers proton transfers within the hydrogen-bonding network comprised of pCA and proximal amino acid residues. Although PYP emits little fluorescence, we succeeded to reconstitute an artificial fluorescent PYP (PYP-coumarin) by substituting the pCA with its trans-lock analog 7-hydroxycoumarin. Spectroscopic studies with PYP-coumarin revealed that the chromophore takes an anionic form at neutral pH, but is protonated by lowering pH. Both the protonated and deprotonated forms of PYP-coumarin emit intense fluorescence, as compared with the native PYP. In addition, both the deprotonated and protonated forms show identical λmax values in their fluorescence spectra, indicating that ESPT occurs in the artificial fluorescent protein.

scholarly journals Large Stokes shift fluorescence activation in an RNA aptamer by intermolecular proton transfer to guanine

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Mateusz Mieczkowski ◽  
Christian Steinmetzger ◽  
Irene Bessi ◽  
Ann-Kathrin Lenz ◽  
Alexander Schmiedel ◽  
...  
Keyword(s):  
Proton Transfer ◽  
Base Pair ◽  
Fluorescent Proteins ◽  
Stokes Shift ◽  
Fluorescence Emission ◽  
Rna Aptamers ◽  
Rna Aptamer ◽  
Time Resolved ◽  
Large Stokes Shift ◽  
Mechanistic Basis

AbstractFluorogenic RNA aptamers are synthetic functional RNAs that specifically bind and activate conditional fluorophores. The Chili RNA aptamer mimics large Stokes shift fluorescent proteins and exhibits high affinity for 3,5-dimethoxy-4-hydroxybenzylidene imidazolone (DMHBI) derivatives to elicit green or red fluorescence emission. Here, we elucidate the structural and mechanistic basis of fluorescence activation by crystallography and time-resolved optical spectroscopy. Two co-crystal structures of the Chili RNA with positively charged DMHBO+ and DMHBI+ ligands revealed a G-quadruplex and a trans-sugar-sugar edge G:G base pair that immobilize the ligand by π-π stacking. A Watson-Crick G:C base pair in the fluorophore binding site establishes a short hydrogen bond between the N7 of guanine and the phenolic OH of the ligand. Ultrafast excited state proton transfer (ESPT) from the neutral chromophore to the RNA was found with a time constant of 130 fs and revealed the mode of action of the large Stokes shift fluorogenic RNA aptamer.

A novel 2-(2′-aminophenyl)benzothiazole derivative displays ESIPT and permits selective detection of Zn2+ ions: experimental and theoretical studies

RSC Advances ◽  
2016 ◽  
Vol 6 (75) ◽  
pp. 71496-71500 ◽  
Author(s):  
Subramaniyan Janakipriya ◽  
Selvaraj Tamilmani ◽  
Sathiah Thennarasu
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Stokes Shift ◽  
Intramolecular Proton Transfer ◽  
Theoretical Studies ◽  
Selective Detection ◽  
Large Stokes Shift ◽  
Benzothiazole Derivative ◽  
Experimental And Theoretical Studies

Synthesis of a novel 2-(2′-aminophenyl)benzothiazole based probe (1) and demonstration of excited state intramolecular proton transfer (ESIPT) with a large Stokes shift (∼246 nm) are presented.

Near-infrared fluorescent dyes with large Stokes shifts: light generation in BODIPYs undergoing excited state intramolecular proton transfer

2017 ◽  
Vol 15 (19) ◽  
pp. 4072-4076 ◽  
Author(s):  
Qiang Fei ◽  
Xianfeng Gu ◽  
Yajing Liu ◽  
Ben Shi ◽  
Hengyan Liu ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Near Infrared ◽  
Fluorescent Dyes ◽  
Stokes Shift ◽  
Intramolecular Proton Transfer ◽  
Large Stokes Shift ◽  
Light Generation ◽  
Stokes Shifts

New ESIPT-based BODIPYs are developed to render the NIR emissions with a large Stokes shift.

scholarly journals Facile Synthesis of an Organic Solid State Near-Infrared-Emitter with Large Stokes Shift via Excited-State Intramolecular Proton Transfer

ACS Omega ◽  
2018 ◽  
Vol 3 (10) ◽  
pp. 14341-14348 ◽  
Author(s):  
Abhishek Kumar Gupta ◽  
Ashwani Kumar ◽  
Ranjit Singh ◽  
Manisha Devi ◽  
Abhimanew Dhir ◽  
...  
Keyword(s):  
Excited State ◽  
Solid State ◽  
Proton Transfer ◽  
Near Infrared ◽  
Stokes Shift ◽  
Intramolecular Proton Transfer ◽  
Facile Synthesis ◽  
Large Stokes Shift ◽  
Organic Solid ◽  
Infrared Emitter

Self-absorption-free excited-state intramolecular proton transfer (ESIPT) emitters for high brightness and luminous efficiency organic fluorescent electroluminescent devices

2021 ◽  
Author(s):  
Jakkapan Kumsampao ◽  
Chaiyon Chaiwai ◽  
Chatatrika Sukpattanacharoen ◽  
Thanyarat Chawanpunyawat ◽  
Phattananawee Nalaoh ◽  
...  
Keyword(s):  
Optical Properties ◽  
Excited State ◽  
Proton Transfer ◽  
Stokes Shift ◽  
Intramolecular Proton Transfer ◽  
Luminous Efficiency ◽  
Attractive Feature ◽  
High Brightness ◽  
Electroluminescent Devices ◽  
Large Stokes Shift

Excited-state intramolecular proton transfer (ESIPT) chromophores with an attractive feature of a large Stokes shift in optical properties have been exceedingly considered as prime candidates for various applications. However, as...

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