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Issue 14, 2012
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7-Amino coumarin based fluorescent phototriggers coupled with nano/bio-conjugated bonds: Synthesis, labeling and photorelease

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Abstract

By several synthetic pathways, we designed and synthesized a new series of unsymmetrical substituted 7-amino coumarin-based phototriggers with various nano/bio-conjugated bonds. The photophysical properties of most of the substituted coumarin-based phototriggers, except for compound P9 with maleimide group, showed no significant change compared with that of 7-(diethylamino)-4-(hydroxylmethyl) coumarin (DEACM-OH, the reported symmetric substituted 7-amine coumarin based phototrigger). Four compounds (P2, P4, P9, 14) were successfully conjugated with typical carriers such as mesoporous silica nanoparticles, biocompatible polymer PEG and common protein BSA, respectively. The efficient photorelease of ibuprofen (IBU) in the model cargo delivery system of MD4 confirmed that our designed phototriggers could serve well as a photo-cage for bioactive molecules and the release can be regulated precisely by manipulating the external irradiation conditions. All the results hinted at the superiority of using these coumarin functional compounds for photo-regulated release in biotechnology and biomedical areas.

Graphical abstract: 7-Amino coumarin based fluorescent phototriggers coupled with nano/bio-conjugated bonds: Synthesis, labeling and photorelease

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Publication details

The article was received on 18 Jan 2012, accepted on 10 Feb 2012 and first published on 13 Feb 2012


Article type: Paper
DOI: 10.1039/C2JM30357D
J. Mater. Chem., 2012,22, 6680-6688

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    7-Amino coumarin based fluorescent phototriggers coupled with nano/bio-conjugated bonds: Synthesis, labeling and photorelease

    Q. Lin, C. Bao, G. Fan, S. Cheng, H. Liu, Z. Liu and L. Zhu, J. Mater. Chem., 2012, 22, 6680
    DOI: 10.1039/C2JM30357D

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