Improving the trapping of superoxide radical with a β-cyclodextrin5- diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO) conjugate

Micaël Hardy, David Bardelang, Hakim Karoui, A. Rockenbauer, Jean Pierre Finet, Laszlo Jicsinszky, Roselyne Rosas, Olivier Ouari, Paul Tordo

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

A study was conducted to demonstrate the preparation and EPR investigation of a new DEPMPO-appended β-cyclodextrin derivative CD-DEPMPO and its performance regarding the superoxide detection in biological system models. CD-DEPMPO was prepared in a one-step sequence with high yield by reacting NHS-DEPMPO binding block with 6-monodeoxy-6-monoamino permethyl β-cyclodextrin (H2N-TRIMEB). ROESY NMR experiments performed on a CD-DEPMPO aqueous solution revealed weak ROE cross-peaks between the signals of the phosphonate methyl groups and those of the methoxy groups of the cyclodextrin primary rim. Additional weak ROE cross-correlations suggested additional weak interactions between the methyl groups and the C5 of the pyrroline ring and the primary rim of the cavity.

Original languageEnglish
Pages (from-to)11114-11118
Number of pages5
JournalChemistry - A European Journal
Volume15
Issue number42
DOIs
Publication statusPublished - Oct 26 2009

Fingerprint

Superoxides
Oxides
Cyclodextrins
Biological systems
Organophosphonates
Paramagnetic resonance
Nuclear magnetic resonance
pyrroline
Derivatives
Experiments

Keywords

  • Blood
  • Cyclodextrins
  • EPR spectroscopy
  • Spin trapping
  • Superoxides

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Improving the trapping of superoxide radical with a β-cyclodextrin5- diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO) conjugate. / Hardy, Micaël; Bardelang, David; Karoui, Hakim; Rockenbauer, A.; Finet, Jean Pierre; Jicsinszky, Laszlo; Rosas, Roselyne; Ouari, Olivier; Tordo, Paul.

In: Chemistry - A European Journal, Vol. 15, No. 42, 26.10.2009, p. 11114-11118.

Research output: Contribution to journalArticle

Hardy, Micaël ; Bardelang, David ; Karoui, Hakim ; Rockenbauer, A. ; Finet, Jean Pierre ; Jicsinszky, Laszlo ; Rosas, Roselyne ; Ouari, Olivier ; Tordo, Paul. / Improving the trapping of superoxide radical with a β-cyclodextrin5- diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO) conjugate. In: Chemistry - A European Journal. 2009 ; Vol. 15, No. 42. pp. 11114-11118.
@article{b958479762f04aacb10b11e88a6f4dc3,
title = "Improving the trapping of superoxide radical with a β-cyclodextrin5- diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO) conjugate",
abstract = "A study was conducted to demonstrate the preparation and EPR investigation of a new DEPMPO-appended β-cyclodextrin derivative CD-DEPMPO and its performance regarding the superoxide detection in biological system models. CD-DEPMPO was prepared in a one-step sequence with high yield by reacting NHS-DEPMPO binding block with 6-monodeoxy-6-monoamino permethyl β-cyclodextrin (H2N-TRIMEB). ROESY NMR experiments performed on a CD-DEPMPO aqueous solution revealed weak ROE cross-peaks between the signals of the phosphonate methyl groups and those of the methoxy groups of the cyclodextrin primary rim. Additional weak ROE cross-correlations suggested additional weak interactions between the methyl groups and the C5 of the pyrroline ring and the primary rim of the cavity.",
keywords = "Blood, Cyclodextrins, EPR spectroscopy, Spin trapping, Superoxides",
author = "Mica{\"e}l Hardy and David Bardelang and Hakim Karoui and A. Rockenbauer and Finet, {Jean Pierre} and Laszlo Jicsinszky and Roselyne Rosas and Olivier Ouari and Paul Tordo",
year = "2009",
month = "10",
day = "26",
doi = "10.1002/chem.200901342",
language = "English",
volume = "15",
pages = "11114--11118",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "42",

}

TY - JOUR

T1 - Improving the trapping of superoxide radical with a β-cyclodextrin5- diethoxyphosphoryl-5-methyl-1-pyrroline-n-oxide (DEPMPO) conjugate

AU - Hardy, Micaël

AU - Bardelang, David

AU - Karoui, Hakim

AU - Rockenbauer, A.

AU - Finet, Jean Pierre

AU - Jicsinszky, Laszlo

AU - Rosas, Roselyne

AU - Ouari, Olivier

AU - Tordo, Paul

PY - 2009/10/26

Y1 - 2009/10/26

N2 - A study was conducted to demonstrate the preparation and EPR investigation of a new DEPMPO-appended β-cyclodextrin derivative CD-DEPMPO and its performance regarding the superoxide detection in biological system models. CD-DEPMPO was prepared in a one-step sequence with high yield by reacting NHS-DEPMPO binding block with 6-monodeoxy-6-monoamino permethyl β-cyclodextrin (H2N-TRIMEB). ROESY NMR experiments performed on a CD-DEPMPO aqueous solution revealed weak ROE cross-peaks between the signals of the phosphonate methyl groups and those of the methoxy groups of the cyclodextrin primary rim. Additional weak ROE cross-correlations suggested additional weak interactions between the methyl groups and the C5 of the pyrroline ring and the primary rim of the cavity.

AB - A study was conducted to demonstrate the preparation and EPR investigation of a new DEPMPO-appended β-cyclodextrin derivative CD-DEPMPO and its performance regarding the superoxide detection in biological system models. CD-DEPMPO was prepared in a one-step sequence with high yield by reacting NHS-DEPMPO binding block with 6-monodeoxy-6-monoamino permethyl β-cyclodextrin (H2N-TRIMEB). ROESY NMR experiments performed on a CD-DEPMPO aqueous solution revealed weak ROE cross-peaks between the signals of the phosphonate methyl groups and those of the methoxy groups of the cyclodextrin primary rim. Additional weak ROE cross-correlations suggested additional weak interactions between the methyl groups and the C5 of the pyrroline ring and the primary rim of the cavity.

KW - Blood

KW - Cyclodextrins

KW - EPR spectroscopy

KW - Spin trapping

KW - Superoxides

UR - http://www.scopus.com/inward/record.url?scp=70350497338&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70350497338&partnerID=8YFLogxK

U2 - 10.1002/chem.200901342

DO - 10.1002/chem.200901342

M3 - Article

C2 - 19760720

AN - SCOPUS:70350497338

VL - 15

SP - 11114

EP - 11118

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 42

ER -