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EnglishFL NBD-BAM PEG2k , bearing a nitrobenzoxadiazole (NBD) unit and an oleyl terminus conjugated via a poly(ethylene glycol) (PEG) spacer (M n = 2,000), was designed to fluorescently label cell membranes by docking its hydrophobic oleyl terminus. During laser scanning microscopy in a minimal essential medium (MEM), human hepatocellular carcinoma Hep3B cells labeled with FL NBD-BAM PEG2k appeared to undergo optoporation at their plasma membrane. We confirmed this unprecedented possibility by a series of cellular uptake experiments using negatively charged and therefore membrane-impermeable quantum dots (QDs; D h = 4.7 nm). Detailed studies indicated that the photoexcited NBD unit can generate singlet oxygen ( 1 O 2 ), which oxidizes the constituent phospholipids to transiently deteriorate the cell membrane. Reference membrane modifiers FL NBD-Oleyl and FL NBD-BAM PEG8k having shorter or longer hydrophilic spacers between the NBD and oleyl units showed a little or substantially no optoporation. For understanding these results, one must consider the following contradictory factors: (1) The photosensitized 1 O 2 generation efficiently occurs only when the NBD unit is in aqueous media, and (2) the lifetime of 1 O 2 in aqueous media is very short (3.0-3.5 μs). As supported experimentally and computationally, the hydrophilic spacer length of FL NBD-BAM PEG2k is optimal for compromising these factors. Further to note, the optoporation using FL NBD-BAM PEG2k is not accompanied by cytotoxicity.
Nitrobenzoxadiazole-Appended Cell Membrane Modifiers for Efficient Optoporation with Noncoherent Light / Otake, S.; Okuro, K.; Bochicchio, D.; Pavan, G. M.; Aida, T.. - In: BIOCONJUGATE CHEMISTRY. - ISSN 1043-1802. - 29:6(2018), pp. 2068-2073.
| Titolo: | Nitrobenzoxadiazole-Appended Cell Membrane Modifiers for Efficient Optoporation with Noncoherent Light |
| Autori: | |
| Data di pubblicazione: | 2018 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.bioconjchem.8b00270 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
File in questo prodotto:
| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| Otake_Preprint-author.pdf | 2. Post-print / Author's Accepted Manuscript | Non Pubblico - Accesso privato/ristretto | Administrator Richiedi una copia | |
| acs.bioconjchem.8b00270.pdf | 2a Post-print versione editoriale / Version of Record | Non Pubblico - Accesso privato/ristretto | Administrator Richiedi una copia | |
| bc8b00270_si_001.pdf | Supporting information (pdf) | Altro materiale allegato | Non Pubblico - Accesso privato/ristretto | Administrator Richiedi una copia |
http://hdl.handle.net/11583/2813816
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