AMPO spin traps

Details AMPO spin traps AMPO spin traps

2005-11-23

2009-10-06

Anderson, Rebecca L (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07598400

ABSTRACT:
Provided are spin traps for the study of radical formation in vivo or in vitro. 5-carbamoyl-5-methyl-1-pyrroline N-oxide (AMPO) and 2-amino-5-carbamoyl-5-methyl-1-pyrroline N-oxide (NH2-AMPO), have the following structures, respectively:as well as salts thereof.

REFERENCES:
Alderson et al. (J. Chem. Soc. Perk. Trans. I, 1976, 1955-60).
Stolze et al. (Biol. Chem., v. 384, p. 493-500, 2003).
Villamena et al. (J. Org. Chem., v69, No. 23, p. 7994-8004 (2004)).
Alderson et al., “Experiments towards the synthesis of corrins. Part XIV.1 Oxidative Decarboxylation of 1-Hydroxypyrrolidine-2-carboxylic acids and oxidation of some Δ1-pyrroline 1-oxides by hypobromite”, J Chem Soc, Perkin Trans, 1, 1976, 1955-1960.
Bonnett et al., “Experiments towards the synthesis of corrins. Part II. The preparation and reactions of Δ1-pyrroline 1-oxides”, J Chem Soc, 1959, pp. 2094-2102.
Chalier et al., “5-Diisopropoxyphosphoryl-5-methyl-a-pyrroline N-oxide, DIPPMPO, a crystalline analog of the nitrone DEPMPO: synthesis and spin trapping properties”, J Chem Soc, Perkin Trans, 2, pp. 2110-2117, 2002.
Chignell, C.F., “Spin trapping studies of photochemical reactions”, Pure & Appl Chem, vol. 62, No. 2, pp. 301-305, 1990.
Frejaville et al., “5-(Diethoxyphosphoryl)-5-methyl-1-pyrroline N-Oxide: A new efficient phosphorylated nitrone for the in vitro and the in vivo spin trapping of oxygen-centered radicals”, J Med Chem, 38, pp. 258-265, 1995.
Liu et al., “Evaluation of DEPMPO as a spin trapping agent in biological systems”, Free Radical Biol. & Medicine, vol. 26, Nos. 5/6, pp. 714-721, 1999.
Olive et al “2-Ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide: Evaulation of the spin trapping properties” Free Radical Biol & Medicine, vol. 28, No. 3, pp. 403-408, 2000.
Rosen et al., “Influence of conformation on the EPR spectrum of 5,5-dimethyl-1-hydroperoxy-2-pyrrolidinyloxyl: a spin trapped adduct of superoxide”, J Org Chem, 69, pp. 1321-1330, 2004.
Stolze et al., “Spin adducts of superoxide, alkoxyl, and lipid-derived radicals with EMPO and its derivatives”, Biol Chem, vol. 383, pp. 813-820, May 2002.
Stolze et al., “Synthesis and characterization of EMPO-derived 5,5-disubstituted 1-pyrroline N-oxides as spin traps forming exceptionally stable superoxide spin adducts”, Biol Chem, vol. 384, pp. 493,500, Mar. 2003.
Stolze et al., “Spin Trapping of lipid radicals with DEPMPO-derived spin traps: Detection of superoxide, aklyl and alkoxyl radicals in aqueous and lipid phase”, Free Radical Biol & Medicine, vol. 29, No. 10, pp. 1005-1014, 2000.
Tsai et al., “Esters of 5-carboxyl-5-methyl-1-pyrroline N-oxide: A family of spin traps for superoxide”, J Org Chem, 68, pp. 7811-7817, 2003.
Turner, III et al., “Spin trapping of superoxide and hydroxyl radicals with substituted pyrroline 1-oxides”, J Med Chem, 29, pp. 2439-2444, 1986.
Villamena et al., “Superoxide radical trapping and spin adduct decay of 5-tert-butoxycarbonyl-5-methyl-1-pyrroline N-oxide (BoxMPO†): kinetics and theoretical analysis” J Chem Soc, Perkin Trans, 2, pp. 1340-1344, 2002.
Zhang et al., “Detection of superoxide anion using an isotopically labeled nitrone spin trap: potential biological applications”, FEBS Letters, 473, pp. 58-62, 2000.
Zhao et al., “Synthesis and biochemical application of a solid cyclic nitrone spin trap: a relatively superior trap for detecting superoxide anions and glutathiyl radicals”, Free Radical Biology & Medicine, vol. 31, No. 5, pp. 599-606, 2001.
Spin Trapping, one page, IUPAC Compendium of Chemical Terminology, 2nd Edition, 1997, 1994, 66, 1166.

Affiliated with

Also associated with

Rating

AMPO spin traps does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with AMPO spin traps, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and AMPO spin traps will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4079899