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. 2024 Jul 15;40(30):15749-15757.
doi: 10.1021/acs.langmuir.4c01575. Online ahead of print.

Surface Chemistry of Cytosporone-B Incorporated in Models for Microbial Biomembranes as Langmuir Monolayers

Guilherme Nuñez Jaroque  1 , Augusto Leonardo Dos Santos  1 , Patricia Sartorelli  1 , Luciano Caseli  1
Affiliations

Surface Chemistry of Cytosporone-B Incorporated in Models for Microbial Biomembranes as Langmuir Monolayers

Guilherme Nuñez Jaroque et al. Langmuir. .

Abstract

Cytosporone-B, a polyketide renowned for its antimicrobial properties, was integrated into Langmuir monolayers composed of dipalmitoylphosphoethanolamine (DPPE) and dioleoylphosphoethanolamine (DOPE) lipids, effectively emulating microbial cytoplasmic membranes. This compound exhibited an expansive influence on DPPE monolayers while inducing condensation in DOPE monolayers. This led to a notable reduction in the compressibility modulus for both lipids, with a more pronounced effect observed for DPPE. The heightened destabilization observed in DOPE monolayers subjected to biologically relevant pressures was particularly noteworthy, as evidenced by surface pressure-time curves at constant area. In-depth analysis using infrared spectroscopy at the air-water interface unveiled alterations in the alkyl chains of the lipids induced by cytosporone-B. This was further corroborated by surface potential measurements, indicating a heightened tilt in the acyl chains upon drug incorporation. Notably, these observed effects did not indicate an aggregating process induced by the drug. Overall, the distinctive impact of cytosporone-B on each lipid underscores the importance of understanding the nuanced effects of microbial drugs on membranes, whether in condensed or fluid states.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Chemical structures of DPPE, DOPE, and Csn-B.
Figure 2
Figure 2
Surface pressure–area (A and C) and surface compressional modulus–surface pressure (B and D) isotherms for DPPE (A and B) and DOPE (C and D) monolayers, alone or with Csn-B. The area per molecule is related only to the lipid.
Figure 3
Figure 3
Surface pressure–time isotherms for DPPE (A) and DOPE (B) monolayers, alone or with Csn-B previously compressed to 30 mN/m at a constant area.
Figure 4
Figure 4
Surface potential–area isotherms for DPPE (A) and DOPE (B) monolayers, alone or with Csn-B.
Figure 5
Figure 5
PM-IRRAS spectra for DPPE (A and B) and DOPE (C and D) monolayers, alone or with Csn-B at the surface pressure of 30 mN/m.
See this image and copyright information in PMC

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