Cellular Uptake of a Fluorescent Calix[4]arene Derivative

Lalor, Ruth; Baillie-Johnson, Hugo; Redshaw, Carl; Matthews, Susan E.; Müeller, Anja

doi:10.1021/ja0782596

Cited by 88 publications

(105 citation statements)

References 22 publications

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“…Interestingly, apparent localization of 1 in the cytosol is consistent with the previously reported localization of calixarenes in Chinese Hamster Ovary (CHO) cells. [43] In the absence of 1 (Figure 3c, A-D), no fluorescence was observed in the nanohoop channel confirming that the signal was not due to cellular auto fluorescence. Additionally, no significant changes in cell morphology were observed through the differential interference contrast (DIC) channel after incubation with 1, confirming a low cytotoxicity of the nanohoop at this concentration.…”

Section: Introductionmentioning

confidence: 70%

Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

White¹,

Yu²,

Kawashima³

et al. 2018

Preprint

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Abstract:The design and optimization of fluorescent molecules has driven the ability to interrogate complex biological events in real time. Notably, most advances in bioimaging fluorophores are based on optimization of core structures that have been known for over a century. Recently, new synthetic methods have resulted in an explosion of non-planar conjugated macrocyclic molecules with unique optical properties yet to be harnessed in a biological context. Herein we report the synthesis of the first aqueous-soluble carbon nanohoop (i.e. a macrocyclic slice of a carbon nanotube prepared via organic synthesis) and demonstrate its bioimaging capabilities in live cells. This work establishes the nanohoops as an exciting new class of macrocyclic fluorophores poised for further development as novel bioimaging tools.

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Section: Introductionmentioning

confidence: 70%

Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

White¹,

Yu²,

Kawashima³

et al. 2018

Preprint

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“…We recently demonstrated that fluorescently labeled calix [4]arene have the potential to track progress of the macrocycle in cells, as an NBD labeled cationic derivative was readily and speedily taken up into cells and provided a very stable, nontoxic read-out system to investigate cellular localization (20). The absorbance and emission spectra for the NBDCalAm showed that it can easily be visualized using a GFP filter (20). …”

mentioning

confidence: 99%

Stable and sensitive probes for lysosomes: Cell‐penetrating fluorescent calix[4]arenes accumulate in acidic vesicles

et al. 2010

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The uptake of a fluorescently labeled cationic calix [4] (NBDCalAm) in live, nonfixed cells has been investigated. The compound is taken into the cells rapidly and shows distinct endosomal distribution after 2 hours. This distribution pattern shows colocalization with lysosomal staining. The uptake is not altered by inhibition of clathrin or caveolae dependent pathways nor by depletion of the cellular ATP-pool. Immediately after uptake the probe is localized in the Golgi and brefeldin A treatment prevents transport to lysosomes. Pulse chase experiments with bafilomycin A1, monensin, and sodium azide showed that accumulation and retention of the probe in lysosomes is primarily driven by the activity of vacuolar ATPases. The NBD labeled calix[4]arene provides a very stable and sensitive marker for lysosomes, and has a considerable advantage over some commercially available lysosomal markers in so far that the fluorescent signal is stable even when the cells are incubated in dye-free medium after staining. ' 2010 International Society for Advancement of Cytometry Key termslysosome; calixarene; cell-penetration; immunofluorescence CALIXARENES (1) are a family of readily synthesized and functionalized macrocycles which have found applications in a number of research areas. In particular the ability of derivatives to complex anions (2,3) and cations (4,5) has been exploited for the development of sensors. Recently, interest has focused on the use of calixarene derivatives in biological systems be it as drugs, drug delivery systems, or imaging agents. In the design of drug molecules, particular attention has been paid to calixarenes as antimicrobials (6-8), as vaccines (9) and as anticancer agents (10). In the field of drug delivery, agents for nucleic acids based on single calixarenes (11-13) have shown promise and we have recently shown that larger arrays of cationic calix[4]arene, so-called multicalixarenes, are able to transfect DNA effectively (14). In addition a number of studies have combined the ability of calixarene derivatives to complex cations with their low toxicity in the development of noncovalently labeled protein MRI imaging agents (15,16).While the nontoxic (17) and non-immunogenicity (18,19) status of calixarenes has been established, less information is available on how calixarenes are processed within cells and their cellular fate, both of which are important features which must be characterized before such derivatives are taken further for clinical development. We recently demonstrated that fluorescently labeled calix [4]arene have the potential to track progress of the macrocycle in cells, as an NBD labeled cationic derivative was readily and speedily taken up into cells and provided a very stable, nontoxic read-out system to investigate cellular localization (20). The absorbance and emission spectra for the NBDCalAm showed that it can easily be visualized using a GFP filter (20).

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“…В останні роки все більша увага з боку біохіміків, молекулярних та клітинних біологів приділяється таким малотоксичним супрамо-лекулярним сполукам, як циклічні олігомери фенолів -каліксарени [50][51][52][53][54]. Так, зазначені сполуки (принаймні деякі з них) демонструють мембранотропну дію, добре проникають крізь ПМ, а також слугують ефекторами (інгібіторами та активаторами) ензиматичних, рецепторних та транспортних мембранозв'язаних протеїнів, пригнічують адгезію клітин, виявляють анти-тромботичну дію, гальмують процеси пухлин-ного росту тощо [53][54][55][56][57].…”

Section: +unclassified

Mg(2+),ATP-dependent plasma membrane calcium pump of smooth muscle cells. ІІ. Regulation of activity

Veklich¹

2015

Ukr.Biochem.J.

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Cellular Uptake of a Fluorescent Calix[4]arene Derivative

Cited by 88 publications

References 22 publications

Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

Stable and sensitive probes for lysosomes: Cell‐penetrating fluorescent calix[4]arenes accumulate in acidic vesicles

Mg(2+),ATP-dependent plasma membrane calcium pump of smooth muscle cells. ІІ. Regulation of activity

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