Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives

Klaus Stolze; Natascha Rohr-Udilova; Thomas Rosenau; Andreas Hofinger; Daniel Kolarich; Hans Nohl

doi:10.1016/j.bmc.2005.12.051

Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives

Klaus Stolze^*, Natascha Rohr-Udilova, Thomas Rosenau, Andreas Hofinger, Daniel Kolarich, Hans Nohl

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

In order to develop spin traps with an optimal ratio between hydrophilic and lipophilic properties, low toxicity, and high stability of spin adducts (especially with superoxide radicals), several EMPO-derived spin traps have recently been synthesized forming more stable superoxide adducts (t_1/2 > 20 min) than DMPO or DEPMPO. In this study, ESR-, ¹H-, and ¹³C-NMR data of several phenyl- or n-pentyl-substituted EMPO derivatives are presented with full signal assignment. Methyl groups at position 3 or 4 stabilized the superoxide adducts considerably. Spin adducts from other oxygen- and carbon-centered radicals (e.g., derived from methanol or linoleic acid hydroperoxide) are also described.

Original language	English
Pages (from-to)	3368-3376
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	10
DOIs	https://doi.org/10.1016/j.bmc.2005.12.051
Publication status	Published - 15 May 2006

Keywords

EMPO derivatives
EPR
Spin trapping
Superoxide

Access to Document

10.1016/j.bmc.2005.12.051

Cite this

@article{6c845e4209d94f07badc5ed65a088efa,

title = "Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives",

abstract = "In order to develop spin traps with an optimal ratio between hydrophilic and lipophilic properties, low toxicity, and high stability of spin adducts (especially with superoxide radicals), several EMPO-derived spin traps have recently been synthesized forming more stable superoxide adducts (t1/2 > 20 min) than DMPO or DEPMPO. In this study, ESR-, 1H-, and 13C-NMR data of several phenyl- or n-pentyl-substituted EMPO derivatives are presented with full signal assignment. Methyl groups at position 3 or 4 stabilized the superoxide adducts considerably. Spin adducts from other oxygen- and carbon-centered radicals (e.g., derived from methanol or linoleic acid hydroperoxide) are also described.",

keywords = "EMPO derivatives, EPR, Spin trapping, Superoxide",

author = "Klaus Stolze and Natascha Rohr-Udilova and Thomas Rosenau and Andreas Hofinger and Daniel Kolarich and Hans Nohl",

year = "2006",

month = may,

day = "15",

doi = "10.1016/j.bmc.2005.12.051",

language = "English",

volume = "14",

pages = "3368--3376",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier",

number = "10",

}

TY - JOUR

T1 - Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives

AU - Stolze, Klaus

AU - Rohr-Udilova, Natascha

AU - Rosenau, Thomas

AU - Hofinger, Andreas

AU - Kolarich, Daniel

AU - Nohl, Hans

PY - 2006/5/15

Y1 - 2006/5/15

N2 - In order to develop spin traps with an optimal ratio between hydrophilic and lipophilic properties, low toxicity, and high stability of spin adducts (especially with superoxide radicals), several EMPO-derived spin traps have recently been synthesized forming more stable superoxide adducts (t1/2 > 20 min) than DMPO or DEPMPO. In this study, ESR-, 1H-, and 13C-NMR data of several phenyl- or n-pentyl-substituted EMPO derivatives are presented with full signal assignment. Methyl groups at position 3 or 4 stabilized the superoxide adducts considerably. Spin adducts from other oxygen- and carbon-centered radicals (e.g., derived from methanol or linoleic acid hydroperoxide) are also described.

AB - In order to develop spin traps with an optimal ratio between hydrophilic and lipophilic properties, low toxicity, and high stability of spin adducts (especially with superoxide radicals), several EMPO-derived spin traps have recently been synthesized forming more stable superoxide adducts (t1/2 > 20 min) than DMPO or DEPMPO. In this study, ESR-, 1H-, and 13C-NMR data of several phenyl- or n-pentyl-substituted EMPO derivatives are presented with full signal assignment. Methyl groups at position 3 or 4 stabilized the superoxide adducts considerably. Spin adducts from other oxygen- and carbon-centered radicals (e.g., derived from methanol or linoleic acid hydroperoxide) are also described.

KW - EMPO derivatives

KW - EPR

KW - Spin trapping

KW - Superoxide

UR - https://www.scopus.com/pages/publications/33645856503

U2 - 10.1016/j.bmc.2005.12.051

DO - 10.1016/j.bmc.2005.12.051

M3 - Article

C2 - 16439134

AN - SCOPUS:33645856503

SN - 0968-0896

VL - 14

SP - 3368

EP - 3376

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 10

ER -

Spin trapping of C- and O-centered radicals with methyl-, ethyl-, pentyl-, and phenyl-substituted EMPO derivatives

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this