Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers

Lamellar gel networks (LGNs) in personal care or pharmaceutical lotions and creams provide an opaque cream appearance and a creamy texture to these products. Within the LGNs, the lamellar gel (Lβ) phase composed of regularly spaced bilayers of surfactants and long-chain fatty alcohols is predominate...

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Main Authors: Chng, Choon-Peng, Gupta, Shikhar, Huang, Changjin
Other Authors: School of Mechanical and Aerospace Engineering
Format: Article
Language:English
Published: 2024
Subjects:
Gel
Online Access:https://hdl.handle.net/10356/180789
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1807892024-10-26T16:49:00Z Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers Chng, Choon-Peng Gupta, Shikhar Huang, Changjin School of Mechanical and Aerospace Engineering Engineering Bioactive compounds Gel Lamellar gel networks (LGNs) in personal care or pharmaceutical lotions and creams provide an opaque cream appearance and a creamy texture to these products. Within the LGNs, the lamellar gel (Lβ) phase composed of regularly spaced bilayers of surfactants and long-chain fatty alcohols is predominately responsible for the unique rheological properties of the LGNs. To extend the shelf life of LGN-containing products, bioactive compounds with antimicrobial properties are often incorporated into the formulation. However, how the protonation state of the bioactive compounds regulates their release from the Lβ-phase bilayers is currently unknown. Using molecular dynamics simulations, we found that the protonated (neutral) form of cinnamic acid, a common antimicrobial food additive, has a retention ratio higher than that of its deprotonated (charged) counterpart in the Lβ-phase bilayer. From free energy calculations, we determined that not only is the protonated molecule more stable in the hydrophobic interior of the bilayer but also the formation of hydrogen-bonded dimers significantly enhances its stability within the bilayer. Thus, the protonation state has a profound impact on bioavailability of the compounds. Our results also highlight the importance of considering possible oligomeric states of molecules when performing calculations to estimate the permeability of molecules within various bilayers. Agency for Science, Technology and Research (A*STAR) Submitted/Accepted version The work was financially supported by the Agency for Science Technology and Research (A*STAR) Biomedical Research Council Strategic Positioning Fund (SPF)-A*STAR-P&G Collaboration grants (APG2013/134 and H23HW10006). 2024-10-25T06:53:12Z 2024-10-25T06:53:12Z 2024 Journal Article Chng, C., Gupta, S. & Huang, C. (2024). Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers. Journal of Physical Chemistry B, 128(29), 7180-7187. https://dx.doi.org/10.1021/acs.jpcb.4c02442 1520-6106 https://hdl.handle.net/10356/180789 10.1021/acs.jpcb.4c02442 38993042 2-s2.0-85198543148 29 128 7180 7187 en APG2013/134 H23HW10006 Journal of Physical Chemistry B © 2024 American Chemical Society. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1021/acs.jpcb.4c02442. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Engineering
Bioactive compounds
Gel
spellingShingle Engineering
Bioactive compounds
Gel
Chng, Choon-Peng
Gupta, Shikhar
Huang, Changjin
Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
description Lamellar gel networks (LGNs) in personal care or pharmaceutical lotions and creams provide an opaque cream appearance and a creamy texture to these products. Within the LGNs, the lamellar gel (Lβ) phase composed of regularly spaced bilayers of surfactants and long-chain fatty alcohols is predominately responsible for the unique rheological properties of the LGNs. To extend the shelf life of LGN-containing products, bioactive compounds with antimicrobial properties are often incorporated into the formulation. However, how the protonation state of the bioactive compounds regulates their release from the Lβ-phase bilayers is currently unknown. Using molecular dynamics simulations, we found that the protonated (neutral) form of cinnamic acid, a common antimicrobial food additive, has a retention ratio higher than that of its deprotonated (charged) counterpart in the Lβ-phase bilayer. From free energy calculations, we determined that not only is the protonated molecule more stable in the hydrophobic interior of the bilayer but also the formation of hydrogen-bonded dimers significantly enhances its stability within the bilayer. Thus, the protonation state has a profound impact on bioavailability of the compounds. Our results also highlight the importance of considering possible oligomeric states of molecules when performing calculations to estimate the permeability of molecules within various bilayers.
author2 School of Mechanical and Aerospace Engineering
author_facet School of Mechanical and Aerospace Engineering
Chng, Choon-Peng
Gupta, Shikhar
Huang, Changjin
format Article
author Chng, Choon-Peng
Gupta, Shikhar
Huang, Changjin
author_sort Chng, Choon-Peng
title Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
title_short Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
title_full Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
title_fullStr Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
title_full_unstemmed Protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
title_sort protonation state of a bioactive compound regulates its release from lamellar gel-phase bilayers
publishDate 2024
url https://hdl.handle.net/10356/180789
_version_ 1814777727610257408