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An imidazole functionalized pentameric thiophene displays different staining patterns in normal and malignant cells
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, The Institute of Technology.
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, Faculty of Science & Engineering.
Linköping University, Department of Clinical and Experimental Medicine, Division of Cell Biology. Linköping University, Faculty of Medicine and Health Sciences.
Linköping University, Department of Physics, Chemistry and Biology, Chemistry. Linköping University, The Institute of Technology.
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2015 (English)In: Frontiers in Chemistry, E-ISSN 2296-2646, Vol. 3Article in journal (Refereed) Published
Abstract [en]

Molecular tools for fluorescent imaging of cells and their components are vital for understanding the function and activity of cells. Here, we report an imidazole functionalized pentameric oligothiophene, p-HTIm, that can be utilized for fluorescent imaging of cells. p-HTIm fluorescence in normal cells appeared in a peripheral punctate pattern partially co-localized with lysosomes, whereas a one-sided perinuclear Golgi associated localization of the dye was observed in malignant cells. The uptake of p-HTIm was temperature dependent and the intracellular target was reached within 1 h after staining. The ability of p-HTIm to stain cells was reduced when the imidazole side chain was chemically altered, verifying that specific imidazole side-chain functionalities are necessary for achieving the observed cellular staining. Our findings confirm that properly functionalized oligothiophenes can be utilized as fluorescent tools for vital staining of cells and that the selectivity towards distinct intracellular targets are highly dependent on the side-chain functionalities along the conjugated thiophene backbone.

Place, publisher, year, edition, pages
2015. Vol. 3
Keyword [en]
Oligothiophenes, fluorescence, cells, imaging, imidazole
National Category
Clinical Medicine Chemical Sciences Medical Biotechnology
Identifiers
URN: urn:nbn:se:liu:diva-121813DOI: 10.3389/fchem.2015.00058ISI: 000373364600001OAI: oai:DiVA.org:liu-121813DiVA: diva2:859483
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Vid tiden för disputation förelåg publikationen som manuskript

Funding agencies:  Swedish Foundation for Strategic Research; GeCONil [POIG.02.03.01-24-099/13]; ERC from the European Research Council

Available from: 2015-10-07 Created: 2015-10-07 Last updated: 2016-04-30Bibliographically approved
In thesis
1. Poly-and oligothiophenes: Optical probes for multimodal fluorescent assessment of biological processes
Open this publication in new window or tab >>Poly-and oligothiophenes: Optical probes for multimodal fluorescent assessment of biological processes
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

One interesting class of molecules in the research field of imaging biological processes is luminescent conjugated polythiophenes, LCPs. These fluorescent probes have a flexible backbone consisting of repetitive thiophene units. Due to this backbone, the probes possess unique abilities to give rise to different spectral signatures depending on their target and environment. LCPs are a polydispersed material meaning there is an uneven distribution of lengths of the probe. Recently, monodispersed chemically well-defined material denoted luminescent conjugated oligothiophenes, LCOs, with an exact number of repetitive units and distinct sidechain functionalities along the backbone has been developed. LCOs have the advantages of being smaller which leads to higher ability to cross the blood brain barrier. The synthesis of minor chemical alterations is also more simplified due to the well-defined materials.

During my doctoral studies I have used both LCPs and LCOs to study biological processes such as conformational variation of protein aggregates in prion diseases and cellular uptake in normal cells and cancer cells. The research has generally been based on the probes capability to emit light upon irradiation and the interaction with their targets has mainly been assessed through variations in fluorescence intensity, emission-and excitation profiles and fluorescence lifetime decay. These studies verified the utility of LCPs and LCOs for staining and discrimination of both prion strains and cell phenotypes. The results also demonstrated the pronounced influence minor chemical modifications have on the LCO´s staining capacity.

Place, publisher, year, edition, pages
Linköping: Linköping University Electronic Press, 2015. 54 p.
Series
Linköping Studies in Science and Technology. Dissertations, ISSN 0345-7524 ; 1693
National Category
Chemical Sciences Cell and Molecular Biology
Identifiers
urn:nbn:se:liu:diva-121815 (URN)10.3384/diss.diva-121815 (DOI)978-91-7685-986-5 (print) (ISBN)
Public defence
2015-11-06, Planck, Fysikhuset, Campus Valla, Linköping, 10:15 (Swedish)
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Supervisors
Available from: 2015-10-07 Created: 2015-10-07 Last updated: 2015-10-07Bibliographically approved

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Magnusson, KarinAppelqvist, HannaCieślar-Pobuda, ArturBäck, MarcusKågedal, BertilJonasson, JonLos, Marek J.Nilsson, Peter R.
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