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The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells

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The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells. / Kaiser, Mathias; Chalapala, Sudharani; Gorzelanny, Christian; Perali, Ramu Sridhar; Goycoolea, Francisco Martin.

In: J PHARM SCI-US, Vol. 105, No. 2, 02.2016, p. 630-638.

Research output: SCORING: Contribution to journal › SCORING: Journal article › Research › peer-review

Harvard

Kaiser, M, Chalapala, S, Gorzelanny, C, Perali, RS & Goycoolea, FM 2016, 'The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells', J PHARM SCI-US, vol. 105, no. 2, pp. 630-638. https://doi.org/10.1016/j.xphs.2015.10.017

APA

Kaiser, M., Chalapala, S., Gorzelanny, C., Perali, R. S., & Goycoolea, F. M. (2016). The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells. J PHARM SCI-US, 105(2), 630-638. https://doi.org/10.1016/j.xphs.2015.10.017

Vancouver

Kaiser M, Chalapala S, Gorzelanny C, Perali RS, Goycoolea FM. The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells. J PHARM SCI-US. 2016 Feb;105(2):630-638. https://doi.org/10.1016/j.xphs.2015.10.017

Bibtex

@article{711ac0dd125a45d494dcd460eb566ef4,
title = "The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells",
abstract = "Capsaicin is known to interfere with tight junctions (TJs) of epithelial cells and therefore to enhance paracellular permeability of poorly absorbable drugs. However, due to its low water solubility, pungency, and cytotoxicity, its pharmacologic use is limited. In this study, we investigated the effect of capsaicin derivatives of synthetic (e.g., 10-hydroxy-N-(4-hydroxy-3-methoxybenzyl)decanamide, etc.) and natural (olvanil and dihydrocapsaicin) origin on Madin-Darby Canine Kidney-C7 cells. Impedance spectroscopy was used to determine the transepithelial electrical resistance and the capacitance. Permeability assays with fluorescein isothiocyanate-dextran were carried out to evaluate the impact on cell permeability. The results show that lipophilicity could play an important role for the interference with TJ and that the mechanism is independent from the ion channel TRPV-1 and hence on the flux of calcium into the cells. In summary, we synthesized 4 derivatives of capsaicin of lower lipophilicity and compared their properties with other well-known vanilloids. We show that these compounds are able to enhance the permeability of a hydrophilic macromolecule, by opening the TJ for a shorter time than capsaicin. This behavior is dependent on the lipophilicity of the molecule. Understanding of these phenomena may lead to better control of administration of therapeutic molecules.",
keywords = "Animals, Capsaicin, Cell Membrane Permeability, Cell Survival, Dogs, Madin Darby Canine Kidney Cells, Tight Junctions, Journal Article, Research Support, Non-U.S. Gov't",
author = "Mathias Kaiser and Sudharani Chalapala and Christian Gorzelanny and Perali, {Ramu Sridhar} and Goycoolea, {Francisco Martin}",
note = "Copyright {\textcopyright} 2016 American Pharmacists Association{\textregistered}. Published by Elsevier Inc. All rights reserved.",
year = "2016",
month = feb,
doi = "10.1016/j.xphs.2015.10.017",
language = "English",
volume = "105",
pages = "630--638",
journal = "J PHARM SCI-US",
issn = "0022-3549",
publisher = "John Wiley and Sons Inc.",
number = "2",

}

RIS

TY - JOUR

T1 - The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin-Darby Canine Kidney Cells

AU - Kaiser, Mathias

AU - Chalapala, Sudharani

AU - Gorzelanny, Christian

AU - Perali, Ramu Sridhar

AU - Goycoolea, Francisco Martin

N1 - Copyright © 2016 American Pharmacists Association®. Published by Elsevier Inc. All rights reserved.

PY - 2016/2

Y1 - 2016/2

N2 - Capsaicin is known to interfere with tight junctions (TJs) of epithelial cells and therefore to enhance paracellular permeability of poorly absorbable drugs. However, due to its low water solubility, pungency, and cytotoxicity, its pharmacologic use is limited. In this study, we investigated the effect of capsaicin derivatives of synthetic (e.g., 10-hydroxy-N-(4-hydroxy-3-methoxybenzyl)decanamide, etc.) and natural (olvanil and dihydrocapsaicin) origin on Madin-Darby Canine Kidney-C7 cells. Impedance spectroscopy was used to determine the transepithelial electrical resistance and the capacitance. Permeability assays with fluorescein isothiocyanate-dextran were carried out to evaluate the impact on cell permeability. The results show that lipophilicity could play an important role for the interference with TJ and that the mechanism is independent from the ion channel TRPV-1 and hence on the flux of calcium into the cells. In summary, we synthesized 4 derivatives of capsaicin of lower lipophilicity and compared their properties with other well-known vanilloids. We show that these compounds are able to enhance the permeability of a hydrophilic macromolecule, by opening the TJ for a shorter time than capsaicin. This behavior is dependent on the lipophilicity of the molecule. Understanding of these phenomena may lead to better control of administration of therapeutic molecules.

AB - Capsaicin is known to interfere with tight junctions (TJs) of epithelial cells and therefore to enhance paracellular permeability of poorly absorbable drugs. However, due to its low water solubility, pungency, and cytotoxicity, its pharmacologic use is limited. In this study, we investigated the effect of capsaicin derivatives of synthetic (e.g., 10-hydroxy-N-(4-hydroxy-3-methoxybenzyl)decanamide, etc.) and natural (olvanil and dihydrocapsaicin) origin on Madin-Darby Canine Kidney-C7 cells. Impedance spectroscopy was used to determine the transepithelial electrical resistance and the capacitance. Permeability assays with fluorescein isothiocyanate-dextran were carried out to evaluate the impact on cell permeability. The results show that lipophilicity could play an important role for the interference with TJ and that the mechanism is independent from the ion channel TRPV-1 and hence on the flux of calcium into the cells. In summary, we synthesized 4 derivatives of capsaicin of lower lipophilicity and compared their properties with other well-known vanilloids. We show that these compounds are able to enhance the permeability of a hydrophilic macromolecule, by opening the TJ for a shorter time than capsaicin. This behavior is dependent on the lipophilicity of the molecule. Understanding of these phenomena may lead to better control of administration of therapeutic molecules.

KW - Animals

KW - Capsaicin

KW - Cell Membrane Permeability

KW - Cell Survival

KW - Dogs

KW - Madin Darby Canine Kidney Cells

KW - Tight Junctions

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1016/j.xphs.2015.10.017

DO - 10.1016/j.xphs.2015.10.017

M3 - SCORING: Journal article

C2 - 26869424

VL - 105

SP - 630

EP - 638

JO - J PHARM SCI-US

JF - J PHARM SCI-US

SN - 0022-3549

IS - 2

ER -