Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells
Summary: Second harmonic generation (SHG)-based probes are useful for nonlinear optical imaging of biological structures, such as the plasma membrane. Several amphiphilic porphyrin-based dyes with high SHG coefficients have been synthesized with different hydrophilic head groups, and their cellular...
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| Format: | Article |
| Language: | English |
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Elsevier
2018-06-01
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| Series: | iScience |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004218300701 |
| _version_ | 1818188160658571264 |
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| author | Anjul Khadria Jan Fleischhauer Igor Boczarow James D. Wilkinson Michael M. Kohl Harry L. Anderson |
| author_facet | Anjul Khadria Jan Fleischhauer Igor Boczarow James D. Wilkinson Michael M. Kohl Harry L. Anderson |
| author_sort | Anjul Khadria |
| collection | DOAJ |
| description | Summary: Second harmonic generation (SHG)-based probes are useful for nonlinear optical imaging of biological structures, such as the plasma membrane. Several amphiphilic porphyrin-based dyes with high SHG coefficients have been synthesized with different hydrophilic head groups, and their cellular targeting has been studied. The probes with cationic head groups localize better at the plasma membrane than the neutral probes with zwitterionic or non-charged ethylene glycol-based head groups. Porphyrin dyes with only dications as hydrophilic head groups localize inside HEK293T cells to give SHG, whereas tricationic dyes localize robustly at the plasma membrane of cells, including neurons, in vitro and ex vivo. The copper(II) complex of the tricationic dye with negligible fluorescence quantum yield works as an SHG-only dye. The free-base tricationic dye has been demonstrated for two-photon fluorescence and SHG-based multimodal imaging. This study demonstrates the importance of a balance between the hydrophobicity and hydrophilicity of amphiphilic dyes for effective plasma membrane localization. : Chemistry; Organic Synthesis; Imaging Methods in Chemistry; Nonlinear Optics Subject Areas: Chemistry, Organic Synthesis, Imaging Methods in Chemistry, Nonlinear Optics |
| first_indexed | 2024-12-11T23:22:31Z |
| format | Article |
| id | doaj.art-a4e910c349e041398f37b14f5e1f047e |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-12-11T23:22:31Z |
| publishDate | 2018-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-a4e910c349e041398f37b14f5e1f047e2022-12-22T00:46:17ZengElsevieriScience2589-00422018-06-014153163Porphyrin Dyes for Nonlinear Optical Imaging of Live CellsAnjul Khadria0Jan Fleischhauer1Igor Boczarow2James D. Wilkinson3Michael M. Kohl4Harry L. Anderson5Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UKDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UKDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UKDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UKDepartment of Physiology, Anatomy and Genetics, University of Oxford, Oxford OX1 3PT, UKDepartment of Chemistry, Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, UK; Corresponding authorSummary: Second harmonic generation (SHG)-based probes are useful for nonlinear optical imaging of biological structures, such as the plasma membrane. Several amphiphilic porphyrin-based dyes with high SHG coefficients have been synthesized with different hydrophilic head groups, and their cellular targeting has been studied. The probes with cationic head groups localize better at the plasma membrane than the neutral probes with zwitterionic or non-charged ethylene glycol-based head groups. Porphyrin dyes with only dications as hydrophilic head groups localize inside HEK293T cells to give SHG, whereas tricationic dyes localize robustly at the plasma membrane of cells, including neurons, in vitro and ex vivo. The copper(II) complex of the tricationic dye with negligible fluorescence quantum yield works as an SHG-only dye. The free-base tricationic dye has been demonstrated for two-photon fluorescence and SHG-based multimodal imaging. This study demonstrates the importance of a balance between the hydrophobicity and hydrophilicity of amphiphilic dyes for effective plasma membrane localization. : Chemistry; Organic Synthesis; Imaging Methods in Chemistry; Nonlinear Optics Subject Areas: Chemistry, Organic Synthesis, Imaging Methods in Chemistry, Nonlinear Opticshttp://www.sciencedirect.com/science/article/pii/S2589004218300701 |
| spellingShingle | Anjul Khadria Jan Fleischhauer Igor Boczarow James D. Wilkinson Michael M. Kohl Harry L. Anderson Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells iScience |
| title | Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells |
| title_full | Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells |
| title_fullStr | Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells |
| title_full_unstemmed | Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells |
| title_short | Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells |
| title_sort | porphyrin dyes for nonlinear optical imaging of live cells |
| url | http://www.sciencedirect.com/science/article/pii/S2589004218300701 |
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