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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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 |
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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 |
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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. |
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School of Mechanical and Aerospace Engineering |
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School of Mechanical and Aerospace Engineering Chng, Choon-Peng Gupta, Shikhar Huang, Changjin |
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Article |
author |
Chng, Choon-Peng Gupta, Shikhar Huang, Changjin |
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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 |
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2024 |
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https://hdl.handle.net/10356/180789 |
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