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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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Peroxalate micelles: a new contrast agent for the detection of hydrogen peroxide. The copolymer (3) forms the scaffold of the peroxalate micelles and contains peroxalate esters and hydrophilic PEG chains. The peroxalate micelles (4) are formed by self-assembly of 3 with fluorescent dyes in aqueous solutions. Hydrogen peroxide diffuses into the micelles and reacts with its peroxalate esters, generating a high energy dioxetanedione intermediate which then chemically excites encapsulated dyes (5), leading to photon emission and the detection of hydrogen peroxide (6).
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f1-ijn-3-471: Peroxalate micelles: a new contrast agent for the detection of hydrogen peroxide. The copolymer (3) forms the scaffold of the peroxalate micelles and contains peroxalate esters and hydrophilic PEG chains. The peroxalate micelles (4) are formed by self-assembly of 3 with fluorescent dyes in aqueous solutions. Hydrogen peroxide diffuses into the micelles and reacts with its peroxalate esters, generating a high energy dioxetanedione intermediate which then chemically excites encapsulated dyes (5), leading to photon emission and the detection of hydrogen peroxide (6).

Mentions: Peroxalate chemiluminescence is a three component reaction between hydrogen peroxide, a peroxalate ester, and a fluorescent dye and has great potential for hydrogen peroxide imaging because of its high sensitivity and excellent specificity (Stevani et al 2000; Arnous et al 2002; Matsumoto 2004). However, the application of peroxalate chemiluminescence for in vivo imaging of hydrogen peroxide is challenging because it requires sequestering fluorescent dyes and peroxalate esters within close proximity in vivo. Peroxalate micelles are designed to sequester peroxalate esters and fluorescent dyes in their core, enabling the three component peroxalate chemiluminescent reaction to occur in response to hydrogen peroxide. The peroxalate micelles (Figure 1) are composed of the amphiphilic polynorbornene copolymer 3 and rubrene, which was chosen as a fluorescent dye because of its high fluorescence quantum efficiency (Stevani et al 2000).


Detection of hydrogen peroxide with chemiluminescent micelles.

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

Peroxalate micelles: a new contrast agent for the detection of hydrogen peroxide. The copolymer (3) forms the scaffold of the peroxalate micelles and contains peroxalate esters and hydrophilic PEG chains. The peroxalate micelles (4) are formed by self-assembly of 3 with fluorescent dyes in aqueous solutions. Hydrogen peroxide diffuses into the micelles and reacts with its peroxalate esters, generating a high energy dioxetanedione intermediate which then chemically excites encapsulated dyes (5), leading to photon emission and the detection of hydrogen peroxide (6).
© Copyright Policy
Related In: Results  -  Collection

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

f1-ijn-3-471: Peroxalate micelles: a new contrast agent for the detection of hydrogen peroxide. The copolymer (3) forms the scaffold of the peroxalate micelles and contains peroxalate esters and hydrophilic PEG chains. The peroxalate micelles (4) are formed by self-assembly of 3 with fluorescent dyes in aqueous solutions. Hydrogen peroxide diffuses into the micelles and reacts with its peroxalate esters, generating a high energy dioxetanedione intermediate which then chemically excites encapsulated dyes (5), leading to photon emission and the detection of hydrogen peroxide (6).
Mentions: Peroxalate chemiluminescence is a three component reaction between hydrogen peroxide, a peroxalate ester, and a fluorescent dye and has great potential for hydrogen peroxide imaging because of its high sensitivity and excellent specificity (Stevani et al 2000; Arnous et al 2002; Matsumoto 2004). However, the application of peroxalate chemiluminescence for in vivo imaging of hydrogen peroxide is challenging because it requires sequestering fluorescent dyes and peroxalate esters within close proximity in vivo. Peroxalate micelles are designed to sequester peroxalate esters and fluorescent dyes in their core, enabling the three component peroxalate chemiluminescent reaction to occur in response to hydrogen peroxide. The peroxalate micelles (Figure 1) are composed of the amphiphilic polynorbornene copolymer 3 and rubrene, which was chosen as a fluorescent dye because of its high fluorescence quantum efficiency (Stevani et al 2000).

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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Related in: MedlinePlus