A Unique Aliphatic Tertiary Amine Chromophore: Fluorescence, Polymer Structure, and Application in Cell Imaging

Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been...

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Published inJournal of the American Chemical Society Vol. 134; no. 51; pp. 20581 - 20584
Main Authors Sun, Miao, Hong, Chun-Yan, Pan, Cai-Yuan
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 26.12.2012
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Abstract Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been observed only in vapor phase. The objective of this study is how to retain the strong fluorescence of tertiary amines in polymers. Tertiary amines as branching units of the hyperbranched poly(amine-ester) (HypET) display relatively strong fluorescence (Φ = 0.11–0.43). The linear polymers with tertiary amines in the backbone or as the side group are only very weakly fluorescent. The tertiary amine of HypET is easily oxidized under ambient conditions, and red-shifting of fluorescence for the oxidized products has been observed. The galactopyranose-modified HypET exhibits low cytotoxicity and bright cell imaging. Thus, this study opens a new route of synthesizing fluorescent materials for cell imaging, biosensing, and drug delivery.
AbstractList Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been observed only in vapor phase. The objective of this study is how to retain the strong fluorescence of tertiary amines in polymers. Tertiary amines as branching units of the hyperbranched poly(amine-ester) (HypET) display relatively strong fluorescence (Φ = 0.11-0.43). The linear polymers with tertiary amines in the backbone or as the side group are only very weakly fluorescent. The tertiary amine of HypET is easily oxidized under ambient conditions, and red-shifting of fluorescence for the oxidized products has been observed. The galactopyranose-modified HypET exhibits low cytotoxicity and bright cell imaging. Thus, this study opens a new route of synthesizing fluorescent materials for cell imaging, biosensing, and drug delivery.
Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been observed only in vapor phase. The objective of this study is how to retain the strong fluorescence of tertiary amines in polymers. Tertiary amines as branching units of the hyperbranched poly(amine-ester) (HypET) display relatively strong fluorescence (Φ = 0.11-0.43). The linear polymers with tertiary amines in the backbone or as the side group are only very weakly fluorescent. The tertiary amine of HypET is easily oxidized under ambient conditions, and red-shifting of fluorescence for the oxidized products has been observed. The galactopyranose-modified HypET exhibits low cytotoxicity and bright cell imaging. Thus, this study opens a new route of synthesizing fluorescent materials for cell imaging, biosensing, and drug delivery.Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been observed only in vapor phase. The objective of this study is how to retain the strong fluorescence of tertiary amines in polymers. Tertiary amines as branching units of the hyperbranched poly(amine-ester) (HypET) display relatively strong fluorescence (Φ = 0.11-0.43). The linear polymers with tertiary amines in the backbone or as the side group are only very weakly fluorescent. The tertiary amine of HypET is easily oxidized under ambient conditions, and red-shifting of fluorescence for the oxidized products has been observed. The galactopyranose-modified HypET exhibits low cytotoxicity and bright cell imaging. Thus, this study opens a new route of synthesizing fluorescent materials for cell imaging, biosensing, and drug delivery.
Author Pan, Cai-Yuan
Sun, Miao
Hong, Chun-Yan
AuthorAffiliation University of Science and Technology of China
AuthorAffiliation_xml – name: University of Science and Technology of China
Author_xml – sequence: 1
  givenname: Miao
  surname: Sun
  fullname: Sun, Miao
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  surname: Hong
  fullname: Hong, Chun-Yan
– sequence: 3
  givenname: Cai-Yuan
  surname: Pan
  fullname: Pan, Cai-Yuan
  email: pcy@ustc.edu.cn
BackLink https://www.ncbi.nlm.nih.gov/pubmed/23215055$$D View this record in MEDLINE/PubMed
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Snippet Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for...
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SubjectTerms cytotoxicity
Dendrimers - analysis
drugs
Fluorescence
fluorescent dyes
Fluorescent Dyes - analysis
Hep G2 Cells
Humans
image analysis
Microscopy, Confocal
photoluminescence
Polyamines - analysis
Polyesters - analysis
polymers
tertiary amines
vapors
Title A Unique Aliphatic Tertiary Amine Chromophore: Fluorescence, Polymer Structure, and Application in Cell Imaging
URI http://dx.doi.org/10.1021/ja310236m
https://www.ncbi.nlm.nih.gov/pubmed/23215055
https://www.proquest.com/docview/1273604733
https://www.proquest.com/docview/2000392747
Volume 134
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