Cysteine-containing peptides having antioxidant properties

Bielicki, John K

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Title: Cysteine-containing peptides having antioxidant properties

Abstract

Cysteine containing amphipathic alpha helices of the exchangeable apolipoproteins, as exemplified by apolipoprotein (apo) A-I.sub.Milano (R173C) and apoA-I.sub.Paris, (R151C) were found to exhibit potent antioxidant activity on phospholipid surfaces. The addition of a free thiol, at the hydrophobic/hydrophilic interface of an amphipathic alpha helix of synthetic peptides that mimic HDL-related proteins, imparts a unique antioxidant activity to these peptides which inhibits lipid peroxidation and protects phospholipids from water-soluble free radical initiators. These peptides can be used as therapeutic agents to combat cardiovascular disease, ischemia, bone disease and other inflammatory related diseases.

Inventors:

Bielicki, John K ^[1]

Castro Valley, CA

Issue Date:: 2009-10-13

Research Org.:: Univ. of California (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1001794

Patent Number(s):: 7601802

Application Number:: 11/177,225

Assignee:: The Regents of the University of California (Oakland, CA)

Patent Classifications (CPCs):: A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07K - PEPTIDES

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A - HUMAN NECESSITIES A61 - MEDICAL OR VETERINARY SCIENCE A61K - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
A61K38/00 - Medicinal preparations containing peptides

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07K - PEPTIDES
C07K14/775 - Apolipopeptides

Show less

DOE Contract Number:: AC03-76SF00098

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 60 APPLIED LIFE SCIENCES

Citation Formats


                    Bielicki, John K. Cysteine-containing peptides having antioxidant properties.  United States: N. p., 2009. 
        Web.

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                    Bielicki, John K. Cysteine-containing peptides having antioxidant properties.  United States.

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                    Bielicki, John K. Tue .  
        "Cysteine-containing peptides having antioxidant properties".  United States.  https://www.osti.gov/servlets/purl/1001794.

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@article{osti_1001794,

  title        = {Cysteine-containing peptides having antioxidant properties},

  author       = {Bielicki, John K},

  abstractNote = {Cysteine containing amphipathic alpha helices of the exchangeable apolipoproteins, as exemplified by apolipoprotein (apo) A-I.sub.Milano (R173C) and apoA-I.sub.Paris, (R151C) were found to exhibit potent antioxidant activity on phospholipid surfaces. The addition of a free thiol, at the hydrophobic/hydrophilic interface of an amphipathic alpha helix of synthetic peptides that mimic HDL-related proteins, imparts a unique antioxidant activity to these peptides which inhibits lipid peroxidation and protects phospholipids from water-soluble free radical initiators. These peptides can be used as therapeutic agents to combat cardiovascular disease, ischemia, bone disease and other inflammatory related diseases.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2009},

  month        = {10}

}

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Patent:

Works referenced in this record:

Studies of Synthetic Peptides of Human Apolipoprotein A-I Containing Tandem Amphipathic α-Helixes ^†
journal, July 1998

Mishra, Vinod K.; Palgunachari, Mayakonda N.; Datta, Geeta
Biochemistry, Vol. 37, Issue 28
https://doi.org/10.1021/bi980042o

High-density lipoprotein cholesterol and coronary artery disease: Survey of the evidence
journal, September 1990

Rifkind, Basil M.
The American Journal of Cardiology, Vol. 66, Issue 6
https://doi.org/10.1016/0002-9149(90)90561-E

Thiol-bearing synthetic peptides retain the antioxidant activity of apolipoproteinA-IMilano
journal, September 2002

Jia, Zhen; Natarajan, Pradeep; Forte, Trudy M.
Biochemical and Biophysical Research Communications, Vol. 297, Issue 2
https://doi.org/10.1016/S0006-291X(02)02143-5

The replacement of arginine by cysteine at residue 151 in Apolipoprotein A-I produces a phenotype similar to that of Apolipoprotein A-I Milano
journal, January 1997

Bruckert, Eric; von Eckardstein, Arnold; Funke, Harald
Atherosclerosis, Vol. 128, Issue 1
https://doi.org/10.1016/S0021-9150(96)05982-5

The Hydrophobic Face Orientation of Apolipoprotein A-I Amphipathic Helix Domain 143–164 Regulates Lecithin:Cholesterol Acyltransferase Activation
journal, May 1998

Sorci-Thomas, Mary G.; Curtiss, Linda; Parks, John S.
Journal of Biological Chemistry, Vol. 273, Issue 19
https://doi.org/10.1074/jbc.273.19.11776

High-density lipoprotein, low-density lipoprotein and coronary artery disease
journal, September 1990

Wilson, Peter W. F.
The American Journal of Cardiology, Vol. 66, Issue 6
https://doi.org/10.1016/0002-9149(90)90562-F

Aromatic Residue Position on the Nonpolar Face of Class A Amphipathic Helical Peptides Determines Biological Activity
journal, April 2004

Datta, Geeta; Epand, Raquel F.; Epand, Richard M.
Journal of Biological Chemistry, Vol. 279, Issue 25
https://doi.org/10.1074/jbc.M314276200

Synthetic amphipathic helical peptides that mimic apolipoprotein A-I in clearing cellular cholesterol.
journal, October 1994

Mendez, A. J.; Anantharamaiah, G. M.; Segrest, J. P.
Journal of Clinical Investigation, Vol. 94, Issue 4
https://doi.org/10.1172/JCI117515

Only the Two End Helixes of Eight Tandem Amphipathic Helical Domains of Human Apo A-I Have Significant Lipid Affinity: Implications for HDL Assembly
journal, February 1996

Palgunachari, Mayakonda N.; Mishra, Vinod K.; Lund-Katz, Sissel
Arteriosclerosis, Thrombosis, and Vascular Biology, Vol. 16, Issue 2
https://doi.org/10.1161/01.ATV.16.2.328

Thematic review series: The Pathogenesis of Atherosclerosis The oxidation hypothesis of atherogenesis: the role of oxidized phospholipids and HDL
journal, April 2004

Navab, Mohamad; Ananthramaiah, G. M.; Reddy, Srinivasa T.
Journal of Lipid Research, Vol. 45, Issue 6
https://doi.org/10.1194/jlr.R400001-JLR200

Effects of Recombinant Apolipoprotein A-I _Milano on Aortic Atherosclerosis in Apolipoprotein E–Deficient Mice
journal, March 1998

Shah, Prediman K.; Nilsson, Jan; Kaul, Sanjay
Circulation, Vol. 97, Issue 8
https://doi.org/10.1161/01.CIR.97.8.780

High-Dose Recombinant Apolipoprotein A-I _Milano Mobilizes Tissue Cholesterol and Rapidly Reduces Plaque Lipid and Macrophage Content in Apolipoprotein E–Deficient Mice: Potential Implications for Acute Plaque Stabilization
journal, June 2001

Shah, Prediman K.; Yano, Juliana; Reyes, Odette
Circulation, Vol. 103, Issue 25
https://doi.org/10.1161/hc2501.092494

Recombinant apolipoprotein A-I Milano reduces intimal thickening after balloon injury in hypercholesterolemic rabbits.
journal, October 1994

Ameli, S.; Hultgardh-Nilsson, A.; Cercek, B.
Circulation, Vol. 90, Issue 4
https://doi.org/10.1161/01.CIR.90.4.1935

Alteration in Apolipoprotein A-I 22-Mer Repeat Order Results in a Decrease in Lecithin:Cholesterol Acyltransferase Reactivity
journal, March 1997

Sorci-Thomas, Mary G.; Curtiss, Linda; Parks, John S.
Journal of Biological Chemistry, Vol. 272, Issue 11
https://doi.org/10.1074/jbc.272.11.7278

Metabolism of apolipoproteins AI and AII in subjects carrying similar apoAI mutations, apoAI Milano and apoAI Paris
journal, February 2000

Perez-Mendez, Oscar; Bruckert, Eric; Franceschini, Guido
Atherosclerosis, Vol. 148, Issue 2
https://doi.org/10.1016/S0021-9150(99)00279-8

ATP-Binding Cassette Transporter A1 (ABCA1) in Macrophages: A Dual Function in Inflammation and Lipid Metabolism?
journal, January 1999

Schmitz, G.; Kaminski, W. E.; Porsch-Özcürümez, M.
Pathobiology, Vol. 67, Issue 5-6
https://doi.org/10.1159/000028100

Apolipoprotein A-I _Milano and Apolipoprotein A-I _Paris Exhibit an Antioxidant Activity Distinct from That of Wild-Type Apolipoprotein A-I ^†
journal, February 2002

Bielicki, John K.; Oda, Michael N.
Biochemistry, Vol. 41, Issue 6
https://doi.org/10.1021/bi011716p

Cysteine Substitutions in Apolipoprotein A-I Primary Structure Modulate Paraoxonase Activity ^†
journal, February 2001

Oda, Michael N.; Bielicki, John K.; Berger, Trish
Biochemistry, Vol. 40, Issue 6
https://doi.org/10.1021/bi001922h

ATP-Binding Cassette Transporter 1 Participates in LDL Oxidation by Artery Wall Cells
journal, November 2002

Reddy, Srinivasa T.; Hama, Susan; Ng, Carey
Arteriosclerosis, Thrombosis, and Vascular Biology, Vol. 22, Issue 11
https://doi.org/10.1161/01.ATV.0000035700.82829.2A

Cardiovascular Status of Carriers of the Apolipoprotein A-I _Milano Mutant: The Limone sul Garda Study
journal, April 2001

Sirtori, Cesare R.; Calabresi, Laura; Franceschini, Guido
Circulation, Vol. 103, Issue 15
https://doi.org/10.1161/01.CIR.103.15.1949

A-Imilano apoprotein. Isolation and characterization of a cysteine-containing variant of the A-I apoprotein from human high density lipoproteins.
journal, November 1980

Weisgraber, K. H.; Bersot, T. P.; Mahley, R. W.
Journal of Clinical Investigation, Vol. 66, Issue 5
https://doi.org/10.1172/JCI109957

A-IMilano apoprotein. Decreased high density lipoprotein cholesterol levels with significant lipoprotein modifications and without clinical atherosclerosis in an Italian family.
journal, November 1980

Franceschini, G.; Sirtori, C. R.; Capurso, A.
Journal of Clinical Investigation, Vol. 66, Issue 5
https://doi.org/10.1172/JCI109956

Apolipoprotein-mediated Plasma Membrane Microsolubilization: ROLE OF LIPID AFFINITY AND MEMBRANE PENETRATION IN THE EFFLUX OF CELLULAR CHOLESTEROL AND PHOSPHOLIPID
journal, January 1999

Gillotte, Kristin L.; Zaiou, Mohamed; Lund-Katz, Sissel
Journal of Biological Chemistry, Vol. 274, Issue 4
https://doi.org/10.1074/jbc.274.4.2021

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Cysteine-containing peptides having antioxidant properties

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Cysteine containing amphipathic alpha helices of the exchangeable apolipoproteins, as exemplified by apolipoprotein (apo) A-I.sub.Milano (R173C) and apoA-I.sub.Paris, (R151C) were found to exhibit potent antioxidant activity on phospholipid surfaces. The addition of a free thiol, at the hydrophobic/hydrophilic interface of an amphipathic alpha helix of synthetic peptides that mimic HDL-related proteins, imparts a unique antioxidant activity to these peptides which inhibits lipid peroxidation and protects phospholipids from water-soluble free radical initiators. These peptides can be used as therapeutic agents to combat cardiovascular disease, ischemia, bone disease and other inflammatory related diseases.
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Similar Records

Title: Cysteine-containing peptides having antioxidant properties

Abstract

Citation Formats

Studies of Synthetic Peptides of Human Apolipoprotein A-I Containing Tandem Amphipathic α-Helixes † journal, July 1998

High-density lipoprotein cholesterol and coronary artery disease: Survey of the evidence journal, September 1990

Thiol-bearing synthetic peptides retain the antioxidant activity of apolipoproteinA-IMilano journal, September 2002

The replacement of arginine by cysteine at residue 151 in Apolipoprotein A-I produces a phenotype similar to that of Apolipoprotein A-I Milano journal, January 1997

The Hydrophobic Face Orientation of Apolipoprotein A-I Amphipathic Helix Domain 143–164 Regulates Lecithin:Cholesterol Acyltransferase Activation journal, May 1998

High-density lipoprotein, low-density lipoprotein and coronary artery disease journal, September 1990

Aromatic Residue Position on the Nonpolar Face of Class A Amphipathic Helical Peptides Determines Biological Activity journal, April 2004

Synthetic amphipathic helical peptides that mimic apolipoprotein A-I in clearing cellular cholesterol. journal, October 1994

Only the Two End Helixes of Eight Tandem Amphipathic Helical Domains of Human Apo A-I Have Significant Lipid Affinity: Implications for HDL Assembly journal, February 1996

Thematic review series: The Pathogenesis of Atherosclerosis The oxidation hypothesis of atherogenesis: the role of oxidized phospholipids and HDL journal, April 2004

Effects of Recombinant Apolipoprotein A-I Milano on Aortic Atherosclerosis in Apolipoprotein E–Deficient Mice journal, March 1998

High-Dose Recombinant Apolipoprotein A-I Milano Mobilizes Tissue Cholesterol and Rapidly Reduces Plaque Lipid and Macrophage Content in Apolipoprotein E–Deficient Mice: Potential Implications for Acute Plaque Stabilization journal, June 2001

Recombinant apolipoprotein A-I Milano reduces intimal thickening after balloon injury in hypercholesterolemic rabbits. journal, October 1994

Alteration in Apolipoprotein A-I 22-Mer Repeat Order Results in a Decrease in Lecithin:Cholesterol Acyltransferase Reactivity journal, March 1997

Metabolism of apolipoproteins AI and AII in subjects carrying similar apoAI mutations, apoAI Milano and apoAI Paris journal, February 2000

ATP-Binding Cassette Transporter A1 (ABCA1) in Macrophages: A Dual Function in Inflammation and Lipid Metabolism? journal, January 1999

Apolipoprotein A-I Milano and Apolipoprotein A-I Paris Exhibit an Antioxidant Activity Distinct from That of Wild-Type Apolipoprotein A-I † journal, February 2002

Cysteine Substitutions in Apolipoprotein A-I Primary Structure Modulate Paraoxonase Activity † journal, February 2001

ATP-Binding Cassette Transporter 1 Participates in LDL Oxidation by Artery Wall Cells journal, November 2002

Cardiovascular Status of Carriers of the Apolipoprotein A-I Milano Mutant: The Limone sul Garda Study journal, April 2001

A-Imilano apoprotein. Isolation and characterization of a cysteine-containing variant of the A-I apoprotein from human high density lipoproteins. journal, November 1980

A-IMilano apoprotein. Decreased high density lipoprotein cholesterol levels with significant lipoprotein modifications and without clinical atherosclerosis in an Italian family. journal, November 1980

Apolipoprotein-mediated Plasma Membrane Microsolubilization: ROLE OF LIPID AFFINITY AND MEMBRANE PENETRATION IN THE EFFLUX OF CELLULAR CHOLESTEROL AND PHOSPHOLIPID journal, January 1999

Studies of Synthetic Peptides of Human Apolipoprotein A-I Containing Tandem Amphipathic α-Helixes ^†
journal, July 1998

High-density lipoprotein cholesterol and coronary artery disease: Survey of the evidence
journal, September 1990

Thiol-bearing synthetic peptides retain the antioxidant activity of apolipoproteinA-IMilano
journal, September 2002

The replacement of arginine by cysteine at residue 151 in Apolipoprotein A-I produces a phenotype similar to that of Apolipoprotein A-I Milano
journal, January 1997

The Hydrophobic Face Orientation of Apolipoprotein A-I Amphipathic Helix Domain 143–164 Regulates Lecithin:Cholesterol Acyltransferase Activation
journal, May 1998

High-density lipoprotein, low-density lipoprotein and coronary artery disease
journal, September 1990

Aromatic Residue Position on the Nonpolar Face of Class A Amphipathic Helical Peptides Determines Biological Activity
journal, April 2004

Synthetic amphipathic helical peptides that mimic apolipoprotein A-I in clearing cellular cholesterol.
journal, October 1994

Only the Two End Helixes of Eight Tandem Amphipathic Helical Domains of Human Apo A-I Have Significant Lipid Affinity: Implications for HDL Assembly
journal, February 1996

Thematic review series: The Pathogenesis of Atherosclerosis The oxidation hypothesis of atherogenesis: the role of oxidized phospholipids and HDL
journal, April 2004

Effects of Recombinant Apolipoprotein A-I _Milano on Aortic Atherosclerosis in Apolipoprotein E–Deficient Mice
journal, March 1998

High-Dose Recombinant Apolipoprotein A-I _Milano Mobilizes Tissue Cholesterol and Rapidly Reduces Plaque Lipid and Macrophage Content in Apolipoprotein E–Deficient Mice: Potential Implications for Acute Plaque Stabilization
journal, June 2001

Recombinant apolipoprotein A-I Milano reduces intimal thickening after balloon injury in hypercholesterolemic rabbits.
journal, October 1994

Alteration in Apolipoprotein A-I 22-Mer Repeat Order Results in a Decrease in Lecithin:Cholesterol Acyltransferase Reactivity
journal, March 1997

Metabolism of apolipoproteins AI and AII in subjects carrying similar apoAI mutations, apoAI Milano and apoAI Paris
journal, February 2000

ATP-Binding Cassette Transporter A1 (ABCA1) in Macrophages: A Dual Function in Inflammation and Lipid Metabolism?
journal, January 1999

Apolipoprotein A-I _Milano and Apolipoprotein A-I _Paris Exhibit an Antioxidant Activity Distinct from That of Wild-Type Apolipoprotein A-I ^†
journal, February 2002

Cysteine Substitutions in Apolipoprotein A-I Primary Structure Modulate Paraoxonase Activity ^†
journal, February 2001

ATP-Binding Cassette Transporter 1 Participates in LDL Oxidation by Artery Wall Cells
journal, November 2002

Cardiovascular Status of Carriers of the Apolipoprotein A-I _Milano Mutant: The Limone sul Garda Study
journal, April 2001

A-Imilano apoprotein. Isolation and characterization of a cysteine-containing variant of the A-I apoprotein from human high density lipoproteins.
journal, November 1980

A-IMilano apoprotein. Decreased high density lipoprotein cholesterol levels with significant lipoprotein modifications and without clinical atherosclerosis in an Italian family.
journal, November 1980

Apolipoprotein-mediated Plasma Membrane Microsolubilization: ROLE OF LIPID AFFINITY AND MEMBRANE PENETRATION IN THE EFFLUX OF CELLULAR CHOLESTEROL AND PHOSPHOLIPID
journal, January 1999