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Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells

This study reports targetable micelles developed after covalent functionalization of α-tocopheryl polyethylene glycol succinate (TPGS) with amino phenylboronic acid (APBA). Nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic results showed successful attachment of APBA to the hydrophili...

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Autores principales: Tiwari, Sanjay, Sarolia, Jayant, Kansara, Vrushti, Chudasama, Nishith A., Prasad, Kamalesh, Ray, Debes, Aswal, Vinod K, Bahadur, Pratap
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7600591/
https://www.ncbi.nlm.nih.gov/pubmed/33019616
http://dx.doi.org/10.3390/polym12102258
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author Tiwari, Sanjay
Sarolia, Jayant
Kansara, Vrushti
Chudasama, Nishith A.
Prasad, Kamalesh
Ray, Debes
Aswal, Vinod K
Bahadur, Pratap
author_facet Tiwari, Sanjay
Sarolia, Jayant
Kansara, Vrushti
Chudasama, Nishith A.
Prasad, Kamalesh
Ray, Debes
Aswal, Vinod K
Bahadur, Pratap
author_sort Tiwari, Sanjay
collection PubMed
description This study reports targetable micelles developed after covalent functionalization of α-tocopheryl polyethylene glycol succinate (TPGS) with amino phenylboronic acid (APBA). Nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic results showed successful attachment of APBA to the hydrophilic segment of TPGS. Dynamic light scattering and small-angle neutron scattering studies revealed that the conjugate self-assembled in water to produce spherical core-shell micelles (14–20 nm) which remained stable against temperature (ca. 25–45 °C) and pH changes. The micelles could solubilize a high payload of paclitaxel (PLX) without exhibiting changes in the average size. However, at the saturation solubility, drug molecules migrated from the core to the shell region and engaged with APBA groups via π–π stacking interaction. Confocal microscopy and cell sorting analyses verified the effective translocation ability of TPGS-APBA micelles in sialic acid (SA) expressing MDA-MB-453 cells. At equivalent PLX dose, TPGS-APBA micelles showed about a twofold improvement in apoptotic death among the cells exposed for 2 h. Our findings indicate that the attachment of APBA can be a potential strategy for improving the intra-cellular localization of carriers among cancer cells expressing SA residues.
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spelling pubmed-76005912020-11-01 Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells Tiwari, Sanjay Sarolia, Jayant Kansara, Vrushti Chudasama, Nishith A. Prasad, Kamalesh Ray, Debes Aswal, Vinod K Bahadur, Pratap Polymers (Basel) Article This study reports targetable micelles developed after covalent functionalization of α-tocopheryl polyethylene glycol succinate (TPGS) with amino phenylboronic acid (APBA). Nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic results showed successful attachment of APBA to the hydrophilic segment of TPGS. Dynamic light scattering and small-angle neutron scattering studies revealed that the conjugate self-assembled in water to produce spherical core-shell micelles (14–20 nm) which remained stable against temperature (ca. 25–45 °C) and pH changes. The micelles could solubilize a high payload of paclitaxel (PLX) without exhibiting changes in the average size. However, at the saturation solubility, drug molecules migrated from the core to the shell region and engaged with APBA groups via π–π stacking interaction. Confocal microscopy and cell sorting analyses verified the effective translocation ability of TPGS-APBA micelles in sialic acid (SA) expressing MDA-MB-453 cells. At equivalent PLX dose, TPGS-APBA micelles showed about a twofold improvement in apoptotic death among the cells exposed for 2 h. Our findings indicate that the attachment of APBA can be a potential strategy for improving the intra-cellular localization of carriers among cancer cells expressing SA residues. MDPI 2020-10-01 /pmc/articles/PMC7600591/ /pubmed/33019616 http://dx.doi.org/10.3390/polym12102258 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tiwari, Sanjay
Sarolia, Jayant
Kansara, Vrushti
Chudasama, Nishith A.
Prasad, Kamalesh
Ray, Debes
Aswal, Vinod K
Bahadur, Pratap
Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
title Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
title_full Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
title_fullStr Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
title_full_unstemmed Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
title_short Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
title_sort synthesis, colloidal characterization and targetability of phenylboronic acid functionalized α-tocopheryl polyethylene glycol succinate in cancer cells
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7600591/
https://www.ncbi.nlm.nih.gov/pubmed/33019616
http://dx.doi.org/10.3390/polym12102258
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