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Chemistry. 2013 Aug 26;19(35):11672-5. doi: 10.1002/chem.201300494. Epub 2013 Jul 12.

Fluorescent hydroxylamine derived from the fragmentation of PAMAM dendrimers for intracellular hypochlorite recognition.

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1
Center for Nanomedicine Research, National Health Research Institutes, 35 Keyan Road Zhunan, 35053 Miaoli, Taiwan.

Abstract

Herein, a promising sensing approach based on the structure fragmentation of poly(amidoamine) (PAMAM) dendrimers for the selective detection of intracellular hypochlorite (OCl(-)) is reported. PAMAM dendrimers were easily disrupted by a cascade of oxidations in the tertiary amines of the dendritic core to produce an unsaturated hydroxylamine with blue fluorescence. Specially, the novel fluorophore was only sensitive to OCl(-), one of reactive oxygen species (ROS), resulting in an irreversible fluorescence turn-off. The fluorescent hydroxylamine was selectively oxidised by OCl(-) to form a labile oxoammonium cation that underwent further degradation. Without using any troublesomely synthetic steps, the novel sensing platform based on the fragmentation of PAMAM dendrimers, can be applied to detect OCl(-) in macrophage cells. The results suggest that the sensing approach may be useful for the detection of intracellular OCl(-) with minimal interference from biological matrixes.

KEYWORDS:

dendrimers; fluorescence; hydroxylamine; hypochlorite; structure fragmentation

PMID:
23853105
DOI:
10.1002/chem.201300494
[Indexed for MEDLINE]
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