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Detection of hydrogen peroxide with chemiluminescent micelles.

Lee D, Erigala VR, Dasari M, Yu J, Dickson RM, Murthy N - Int J Nanomedicine (2008)

Bottom Line: In this communication, we present a new contrast agent for hydrogen peroxide, termed peroxalate micelles, which detect hydrogen peroxide through chemiluminescence, and have the physical/chemical properties needed for in vivo imaging applications.The peroxalate micelles can detect nanomolar concentrations of hydrogen peroxide (>50 nM) and thus have the sensitivity needed to detect physiological concentrations of hydrogen peroxide.We anticipate numerous applications of the peroxalate micelles for in vivo imaging of hydrogen peroxide, given their high sensitivity, small size, and biocompatible PEG corona.

View Article: PubMed Central - PubMed

Affiliation: The Wallace H. Coulter Department of Biomedical Engineering, Georgia Institute of Technology, Atlanta, GA 30332, USA.

ABSTRACT
The overproduction of hydrogen peroxide is implicated in the progress of numerous life-threatening diseases and there is a great need for the development of contrast agents that can detect hydrogen peroxide in vivo. In this communication, we present a new contrast agent for hydrogen peroxide, termed peroxalate micelles, which detect hydrogen peroxide through chemiluminescence, and have the physical/chemical properties needed for in vivo imaging applications. The peroxalate micelles are composed of amphiphilic peroxalate based copolymers and the fluorescent dye rubrene, they have a 'stealth' polyethylene glycol (PEG) corona to evade macrophage phagocytosis, and a diameter of 33 nm to enhance extravasation into permeable tissues. The peroxalate micelles can detect nanomolar concentrations of hydrogen peroxide (>50 nM) and thus have the sensitivity needed to detect physiological concentrations of hydrogen peroxide. We anticipate numerous applications of the peroxalate micelles for in vivo imaging of hydrogen peroxide, given their high sensitivity, small size, and biocompatible PEG corona.

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Synthesis of amphiphilic polynorbornene copolymer (3) by ROMP.
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f4-ijn-3-471: Synthesis of amphiphilic polynorbornene copolymer (3) by ROMP.

Mentions: A major challenge in developing contrast agents based on peroxalate chemiluminescence is a lack of synthetic techniques for generating polymeric peroxalate esters. The only current methodology for the synthesis of linear polymeric peroxalate esters is through the reaction of oxalyl chloride with diols. However, this polymerization method is not suitable for the development of amphiphilic block copolymers that have well-defined structures. In this study, ring opening metathesis polymerization (ROMP) was employed as a new route for the synthesis of amphiphilic peroxalate copolymers. A ROMP-based synthetic strategy was chosen because ROMP is an efficient and powerful method to synthesize amphiphilic copolymers which have a well-defined structure (Stubenrauch et al 2006; Feng et al 2002). In addition, peroxalate esters which are unstable in the presence of nucleophiles and water can tolerate ROMP reaction conditions (Scheme 1).


Detection of hydrogen peroxide with chemiluminescent micelles.

Lee D, Erigala VR, Dasari M, Yu J, Dickson RM, Murthy N - Int J Nanomedicine (2008)

Synthesis of amphiphilic polynorbornene copolymer (3) by ROMP.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2636589&req=5

f4-ijn-3-471: Synthesis of amphiphilic polynorbornene copolymer (3) by ROMP.
Mentions: A major challenge in developing contrast agents based on peroxalate chemiluminescence is a lack of synthetic techniques for generating polymeric peroxalate esters. The only current methodology for the synthesis of linear polymeric peroxalate esters is through the reaction of oxalyl chloride with diols. However, this polymerization method is not suitable for the development of amphiphilic block copolymers that have well-defined structures. In this study, ring opening metathesis polymerization (ROMP) was employed as a new route for the synthesis of amphiphilic peroxalate copolymers. A ROMP-based synthetic strategy was chosen because ROMP is an efficient and powerful method to synthesize amphiphilic copolymers which have a well-defined structure (Stubenrauch et al 2006; Feng et al 2002). In addition, peroxalate esters which are unstable in the presence of nucleophiles and water can tolerate ROMP reaction conditions (Scheme 1).

Bottom Line: In this communication, we present a new contrast agent for hydrogen peroxide, termed peroxalate micelles, which detect hydrogen peroxide through chemiluminescence, and have the physical/chemical properties needed for in vivo imaging applications.The peroxalate micelles can detect nanomolar concentrations of hydrogen peroxide (>50 nM) and thus have the sensitivity needed to detect physiological concentrations of hydrogen peroxide.We anticipate numerous applications of the peroxalate micelles for in vivo imaging of hydrogen peroxide, given their high sensitivity, small size, and biocompatible PEG corona.

View Article: PubMed Central - PubMed

Affiliation: The Wallace H. Coulter Department of Biomedical Engineering, Georgia Institute of Technology, Atlanta, GA 30332, USA.

ABSTRACT
The overproduction of hydrogen peroxide is implicated in the progress of numerous life-threatening diseases and there is a great need for the development of contrast agents that can detect hydrogen peroxide in vivo. In this communication, we present a new contrast agent for hydrogen peroxide, termed peroxalate micelles, which detect hydrogen peroxide through chemiluminescence, and have the physical/chemical properties needed for in vivo imaging applications. The peroxalate micelles are composed of amphiphilic peroxalate based copolymers and the fluorescent dye rubrene, they have a 'stealth' polyethylene glycol (PEG) corona to evade macrophage phagocytosis, and a diameter of 33 nm to enhance extravasation into permeable tissues. The peroxalate micelles can detect nanomolar concentrations of hydrogen peroxide (>50 nM) and thus have the sensitivity needed to detect physiological concentrations of hydrogen peroxide. We anticipate numerous applications of the peroxalate micelles for in vivo imaging of hydrogen peroxide, given their high sensitivity, small size, and biocompatible PEG corona.

Show MeSH
Related in: MedlinePlus