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Article

Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments

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“Petru Poni” Institute of Macromolecular Chemistry, Romanian Academy, Grigore Ghica Voda Alley 41 A, 700487 Iasi, Romania
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Alexandru Ioan Cuza University of Iasi, Chemistry Department, 11 Carol I, 700506 Iasi, Romania
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Institute of Molecular Biology and Genetics, NASU, 150 Zabolotnogo St., 03143 Kyiv, Ukraine
4
Scientific Services Company Otava Ltd., 150 Zabolotnogo St., 03143 Kyiv, Ukraine
*
Author to whom correspondence should be addressed.
Academic Editors: Estrella Núñez Delicado and José Antonio Gabaldón Hernández
Molecules 2020, 25(19), 4397; https://doi.org/10.3390/molecules25194397
Received: 7 August 2020 / Revised: 18 September 2020 / Accepted: 21 September 2020 / Published: 24 September 2020
(This article belongs to the Special Issue Cyclodextrins: Recent Advances in Chemistry and Applications)
We have designed and synthesized a series of novel, supramolecular, long-lived fluorescent probes based on the host-guest inclusion complexes formation between fluorescent indolizinyl-pyridinium salts and β-cyclodextrin. Fluorescence and electrospray ionisation mass spectrometry experiments, supported by theoretical molecular docking studies, were utilized in the monitoring of the inclusion complexes formation, evidencing the appearance of corresponding 1:1 and 1:2 species. Additionally, the influence of the guest molecule over the aggregation processes of the cyclodextrin inclusion complexes was investigated by transmission electron microscopy. The absence of cytotoxicity, cellular permeability, long-lived intracellular fluorescence, and in time specific accumulation within acidic organelles identified the investigated supramolecular entities as remarkable candidates for intracellular fluorescence probes. Co-staining experiments using specific organelle markers revealed the fact that, after a 24-h incubation period, the inclusion complexes accumulate predominantly in lysosomes rather than in mitochondria. This study opens new possibilities for a broad range of fluorescent dyes with solubility and high toxicity issues, able to form inclusion complexes with β-cyclodextrin, to be tested as intracellular fluorescence probes. View Full-Text
Keywords: fluorescent indolizines; cyclodextrin inclusion complex; molecular docking; in vitro experiments; organelle markers fluorescent indolizines; cyclodextrin inclusion complex; molecular docking; in vitro experiments; organelle markers
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MDPI and ACS Style

Sardaru, M.-C.; Carp, O.; Ursu, E.-L.; Craciun, A.-M.; Cojocaru, C.; Silion, M.; Kovalska, V.; Mangalagiu, I.; Danac, R.; Rotaru, A. Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments. Molecules 2020, 25, 4397. https://doi.org/10.3390/molecules25194397

AMA Style

Sardaru M-C, Carp O, Ursu E-L, Craciun A-M, Cojocaru C, Silion M, Kovalska V, Mangalagiu I, Danac R, Rotaru A. Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments. Molecules. 2020; 25(19):4397. https://doi.org/10.3390/molecules25194397

Chicago/Turabian Style

Sardaru, Monica-Cornelia, Oana Carp, Elena-Laura Ursu, Anda-Mihaela Craciun, Corneliu Cojocaru, Mihaela Silion, Vladyslava Kovalska, Ionel Mangalagiu, Ramona Danac, and Alexandru Rotaru. 2020. "Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments" Molecules 25, no. 19: 4397. https://doi.org/10.3390/molecules25194397

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