An acrylated isocyanonaphthalene based solvatochromic click reagent: Optical and biolabeling properties and quantum chemical modeling

Miklós Nagy, Dávid Rácz, Zsolt László Nagy, Tibor Nagy, Péter Pál Fehér, Mihály Purgel, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The optical and biolabeling properties of a novel molecule 1-(2-acryloyloxy-3-chloro-prop-1-yl)-amino-5-isocyanonaphthalene (ACAIN) is reported. In addition to being a real solvatochromic fluorophore it reacts quantitatively and rapidly with simple thiols in a thiol-ene click reaction. DFT calculations revealed a dark nonfluorescent state of ACAIN due to a close energy triplet state where electron transition can happen between the acrylic double bond and the aromatic core through an intramolecular hydrogen bond between the NH and [Formula presented] moieties. The hydrothiolation reaction is accompanied by a 1.5–19 fold increase in fluorescence intensity depending on the solvent used owing to the saturation of the acrylic group. The quantum yield and reactivity of the molecules were found to be largely dependent on the substituent of the acryl moiety. The biolabeling properties were investigated in detail by fluorometry and electrospray ionization (ESI) mass spectrometry using cysteine, KAC as a simple tripeptide and BSA as a model protein.

Original languageEnglish
Pages (from-to)445-457
Number of pages13
JournalDyes and Pigments
Volume133
DOIs
Publication statusPublished - Oct 1 2016

Fingerprint

Sulfhydryl Compounds
Acrylics
Electrospray ionization
Molecules
Fluorophores
Quantum yield
Electron transitions
Discrete Fourier transforms
Electron energy levels
Mass spectrometry
Cysteine
Hydrogen bonds
Fluorescence
Proteins

Keywords

  • Bovine serum albumin
  • Click reaction
  • Density-functional calculations
  • Fluorescence
  • Solvatochromism

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

An acrylated isocyanonaphthalene based solvatochromic click reagent : Optical and biolabeling properties and quantum chemical modeling. / Nagy, Miklós; Rácz, Dávid; Nagy, Zsolt László; Nagy, Tibor; Fehér, Péter Pál; Purgel, Mihály; Zsuga, M.; Kéki, S.

In: Dyes and Pigments, Vol. 133, 01.10.2016, p. 445-457.

Research output: Contribution to journalArticle

Nagy, Miklós ; Rácz, Dávid ; Nagy, Zsolt László ; Nagy, Tibor ; Fehér, Péter Pál ; Purgel, Mihály ; Zsuga, M. ; Kéki, S. / An acrylated isocyanonaphthalene based solvatochromic click reagent : Optical and biolabeling properties and quantum chemical modeling. In: Dyes and Pigments. 2016 ; Vol. 133. pp. 445-457.
@article{49bb98ff083e431b8b46fdd8a071baa1,
title = "An acrylated isocyanonaphthalene based solvatochromic click reagent: Optical and biolabeling properties and quantum chemical modeling",
abstract = "The optical and biolabeling properties of a novel molecule 1-(2-acryloyloxy-3-chloro-prop-1-yl)-amino-5-isocyanonaphthalene (ACAIN) is reported. In addition to being a real solvatochromic fluorophore it reacts quantitatively and rapidly with simple thiols in a thiol-ene click reaction. DFT calculations revealed a dark nonfluorescent state of ACAIN due to a close energy triplet state where electron transition can happen between the acrylic double bond and the aromatic core through an intramolecular hydrogen bond between the NH and [Formula presented] moieties. The hydrothiolation reaction is accompanied by a 1.5–19 fold increase in fluorescence intensity depending on the solvent used owing to the saturation of the acrylic group. The quantum yield and reactivity of the molecules were found to be largely dependent on the substituent of the acryl moiety. The biolabeling properties were investigated in detail by fluorometry and electrospray ionization (ESI) mass spectrometry using cysteine, KAC as a simple tripeptide and BSA as a model protein.",
keywords = "Bovine serum albumin, Click reaction, Density-functional calculations, Fluorescence, Solvatochromism",
author = "Mikl{\'o}s Nagy and D{\'a}vid R{\'a}cz and Nagy, {Zsolt L{\'a}szl{\'o}} and Tibor Nagy and Feh{\'e}r, {P{\'e}ter P{\'a}l} and Mih{\'a}ly Purgel and M. Zsuga and S. K{\'e}ki",
year = "2016",
month = "10",
day = "1",
doi = "10.1016/j.dyepig.2016.06.036",
language = "English",
volume = "133",
pages = "445--457",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - An acrylated isocyanonaphthalene based solvatochromic click reagent

T2 - Optical and biolabeling properties and quantum chemical modeling

AU - Nagy, Miklós

AU - Rácz, Dávid

AU - Nagy, Zsolt László

AU - Nagy, Tibor

AU - Fehér, Péter Pál

AU - Purgel, Mihály

AU - Zsuga, M.

AU - Kéki, S.

PY - 2016/10/1

Y1 - 2016/10/1

N2 - The optical and biolabeling properties of a novel molecule 1-(2-acryloyloxy-3-chloro-prop-1-yl)-amino-5-isocyanonaphthalene (ACAIN) is reported. In addition to being a real solvatochromic fluorophore it reacts quantitatively and rapidly with simple thiols in a thiol-ene click reaction. DFT calculations revealed a dark nonfluorescent state of ACAIN due to a close energy triplet state where electron transition can happen between the acrylic double bond and the aromatic core through an intramolecular hydrogen bond between the NH and [Formula presented] moieties. The hydrothiolation reaction is accompanied by a 1.5–19 fold increase in fluorescence intensity depending on the solvent used owing to the saturation of the acrylic group. The quantum yield and reactivity of the molecules were found to be largely dependent on the substituent of the acryl moiety. The biolabeling properties were investigated in detail by fluorometry and electrospray ionization (ESI) mass spectrometry using cysteine, KAC as a simple tripeptide and BSA as a model protein.

AB - The optical and biolabeling properties of a novel molecule 1-(2-acryloyloxy-3-chloro-prop-1-yl)-amino-5-isocyanonaphthalene (ACAIN) is reported. In addition to being a real solvatochromic fluorophore it reacts quantitatively and rapidly with simple thiols in a thiol-ene click reaction. DFT calculations revealed a dark nonfluorescent state of ACAIN due to a close energy triplet state where electron transition can happen between the acrylic double bond and the aromatic core through an intramolecular hydrogen bond between the NH and [Formula presented] moieties. The hydrothiolation reaction is accompanied by a 1.5–19 fold increase in fluorescence intensity depending on the solvent used owing to the saturation of the acrylic group. The quantum yield and reactivity of the molecules were found to be largely dependent on the substituent of the acryl moiety. The biolabeling properties were investigated in detail by fluorometry and electrospray ionization (ESI) mass spectrometry using cysteine, KAC as a simple tripeptide and BSA as a model protein.

KW - Bovine serum albumin

KW - Click reaction

KW - Density-functional calculations

KW - Fluorescence

KW - Solvatochromism

UR - http://www.scopus.com/inward/record.url?scp=84976370509&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84976370509&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2016.06.036

DO - 10.1016/j.dyepig.2016.06.036

M3 - Article

AN - SCOPUS:84976370509

VL - 133

SP - 445

EP - 457

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

ER -