Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface
Cell membrane models are useful for obtaining molecular-level information on the interaction of biologically active molecules whose activity is believed to depend also on their effects on the membrane. Cytarabine was conjugated with fatty acids to improve the drug lipophilicity and the interaction w...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-09-01
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| Series: | Membranes |
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| Online Access: | https://www.mdpi.com/2077-0375/12/10/937 |
| _version_ | 1797471587668066304 |
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| author | Jhon Fernando Berrio Escobar Cristiano Giordani Stefano Russo Francesco Castelli Maria Grazia Sarpietro |
| author_facet | Jhon Fernando Berrio Escobar Cristiano Giordani Stefano Russo Francesco Castelli Maria Grazia Sarpietro |
| author_sort | Jhon Fernando Berrio Escobar |
| collection | DOAJ |
| description | Cell membrane models are useful for obtaining molecular-level information on the interaction of biologically active molecules whose activity is believed to depend also on their effects on the membrane. Cytarabine was conjugated with fatty acids to improve the drug lipophilicity and the interaction with the biomembrane model. Cytarabine was conjugated with fatty acids of different lengths to form the trimyristoyl cytarabine and the tristearoyl cytarabine derivatives. Their interaction with biomembrane models constituted by dimyristoylphosphatidylcholine (DMPC) monolayers was studied by employing the Langmuir–Blodgett technique. DMPC/cytarabine, DMPC/trimyristoyl cytarabine and DMPC/tristearoyl cytarabine mixed monolayers at increasing molar fractions of the compound were prepared and placed on the subphase. The mean molecular area/surface pressure isotherms were recorded at 37 °C. Between the molecules of DMPC and those of cytarabine or prodrugs, repulsive forces act. However, these forces are very weak between DMPC and cytarabine and stronger between DMPC and the cytarabine derivatives, thus avoiding the expulsion of the compounds at higher surface pressure and modifying the stability of the mixed monolayer. The fatty acid moieties could then modulate the affinity of cytarabine for biomembranes. |
| first_indexed | 2024-03-09T19:50:13Z |
| format | Article |
| id | doaj.art-81cc1af3436f44e195b75e1e0294ccae |
| institution | Directory Open Access Journal |
| issn | 2077-0375 |
| language | English |
| last_indexed | 2024-03-09T19:50:13Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Membranes |
| spelling | doaj.art-81cc1af3436f44e195b75e1e0294ccae2023-11-24T01:13:00ZengMDPI AGMembranes2077-03752022-09-01121093710.3390/membranes12100937Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water InterfaceJhon Fernando Berrio Escobar0Cristiano Giordani1Stefano Russo2Francesco Castelli3Maria Grazia Sarpietro4Grupo Productos Naturales Marinos, Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Calle 70 No. 52-21, Medellín 050010, ColombiaGrupo Productos Naturales Marinos, Facultad de Ciencias Farmacéuticas y Alimentarias, Universidad de Antioquia, Calle 70 No. 52-21, Medellín 050010, ColombiaDipartimento di Scienze del Farmaco e della Salute, Università degli Studi di Catania, Viale A. Doria 6, 95125 Catania, ItalyDipartimento di Scienze del Farmaco e della Salute, Università degli Studi di Catania, Viale A. Doria 6, 95125 Catania, ItalyDipartimento di Scienze del Farmaco e della Salute, Università degli Studi di Catania, Viale A. Doria 6, 95125 Catania, ItalyCell membrane models are useful for obtaining molecular-level information on the interaction of biologically active molecules whose activity is believed to depend also on their effects on the membrane. Cytarabine was conjugated with fatty acids to improve the drug lipophilicity and the interaction with the biomembrane model. Cytarabine was conjugated with fatty acids of different lengths to form the trimyristoyl cytarabine and the tristearoyl cytarabine derivatives. Their interaction with biomembrane models constituted by dimyristoylphosphatidylcholine (DMPC) monolayers was studied by employing the Langmuir–Blodgett technique. DMPC/cytarabine, DMPC/trimyristoyl cytarabine and DMPC/tristearoyl cytarabine mixed monolayers at increasing molar fractions of the compound were prepared and placed on the subphase. The mean molecular area/surface pressure isotherms were recorded at 37 °C. Between the molecules of DMPC and those of cytarabine or prodrugs, repulsive forces act. However, these forces are very weak between DMPC and cytarabine and stronger between DMPC and the cytarabine derivatives, thus avoiding the expulsion of the compounds at higher surface pressure and modifying the stability of the mixed monolayer. The fatty acid moieties could then modulate the affinity of cytarabine for biomembranes.https://www.mdpi.com/2077-0375/12/10/937cytarabinecytarabine derivativesDMPCLangmuir–Blodgettbiomembrane models |
| spellingShingle | Jhon Fernando Berrio Escobar Cristiano Giordani Stefano Russo Francesco Castelli Maria Grazia Sarpietro Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface Membranes cytarabine cytarabine derivatives DMPC Langmuir–Blodgett biomembrane models |
| title | Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface |
| title_full | Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface |
| title_fullStr | Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface |
| title_full_unstemmed | Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface |
| title_short | Interaction of Lipophilic Cytarabine Derivatives with Biomembrane Model at the Air/Water Interface |
| title_sort | interaction of lipophilic cytarabine derivatives with biomembrane model at the air water interface |
| topic | cytarabine cytarabine derivatives DMPC Langmuir–Blodgett biomembrane models |
| url | https://www.mdpi.com/2077-0375/12/10/937 |
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