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Perylene-Derived Single-Component Organic Nanoparticles with Tunable Emission: Efficient Anticancer Drug Carriers with Real-Time Monitoring of Drug Release
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
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2014 (English)In: ACS Nano, ISSN 1936-0851, E-ISSN 1936-086X, Vol. 8, no 6, 5939-5952 p.Article in journal (Refereed) Published
Abstract [en]

An organic nanoparticle-based drug delivery system with high drug loading efficacy (similar to 79 wt %) was developed using a perylene-derived photoremovable protecting group, namely, perylene-3,4,9,10-tetrayltetramethanol (Pe(OH)(4)). The anticancer drug chlorambucil was protected by coupling with Pe(OH)(4) to form photocaged nanoparticles (Pe(OH)(4)). The photorelease mechanism of chlorambucil from the Pe(Cbl)(4) conjugate was investigated experimentally by high-resolution mass spectrometry and theoretically by density functional theory calculations. The Pe(Cbl)(4) nanoparticles perform four important roles: (i) a nanocarrier for drug delivery, (ii) a phototrigger for drug release, (iii) a fluorescent chromophore for cell imaging, and (iv) a photoswitchable fluorophore for real-time monitoring of drug release. Tunable emission of the perylene-derived nanoparticles was demonstrated by comparing the emission properties of the Pe(OH)(4) and Pe(Cbl)(4) nanoparticles with perylene-3-ylmethanol. These nanoparticles were subsequently employed in cell imaging for investigating their intracellular localization. Furthermore, the in vivo toxicity of the Pe(OH)(4) nanoparticles was investigated using the mouse model. Histological tissue analysis of five major organs, i.e., heart, kidney, spleen, liver, and lung, indicates that the nanoparticles did not show any obvious damage to these major organs under the experimental conditions. The current research presents a successful example of integrating multiple functions into single-component organic nanoparticles for drug delivery.

Place, publisher, year, edition, pages
2014. Vol. 8, no 6, 5939-5952 p.
Keyword [en]
chlorambucil, drug delivery, organic nanoparticles, photoremovable protecting group, tunable emission
National Category
Other Chemistry Topics Biological Sciences
Identifiers
URN: urn:nbn:se:kth:diva-148306DOI: 10.1021/nn501073xISI: 000338089200058Scopus ID: 2-s2.0-84903455670OAI: oai:DiVA.org:kth-148306DiVA: diva2:736765
Funder
Carl Tryggers foundation
Note

QC 20140808

Available from: 2014-08-08 Created: 2014-08-05 Last updated: 2017-12-05Bibliographically approved

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Li, XinÅgren, Hans

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