Structural and thermodynamic characterization of doxycycline/β-cyclodextrin supramolecular complex and its bacterial membrane interactions
Doxycycline is a semi-synthetic antibiotic commonly used for the treatment of many aerobic and anaerobic bacteria. It inhibits the activity of matrix metalloproteinases (MMPs) and affects cell proliferation. In this study, the structural and thermodynamic parameters of free DOX and a DOX/βCD complex...
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| Veröffentlicht in: | Colloids and surfaces, B, Biointerfaces B, Biointerfaces, 2014-06, Vol.118, p.194-201 |
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| creator | Suárez, Diego F Consuegra, Jessika Trajano, Vivianne C Gontijo, Sávio M L Guimarães, Pedro P G Cortés, Maria E Denadai, Ângelo L Sinisterra, Rubén D |
| description | Doxycycline is a semi-synthetic antibiotic commonly used for the treatment of many aerobic and anaerobic bacteria. It inhibits the activity of matrix metalloproteinases (MMPs) and affects cell proliferation. In this study, the structural and thermodynamic parameters of free DOX and a DOX/βCD complex were investigated, as well as their interactions and effects on Staphylococcus aureus cells and cellular cytotoxicity. Complexation of DOX and βCD was confirmed to be an enthalpy- and entropy-driven process, and a low equilibrium constant was obtained. Treatment of S. aureus with higher concentrations of DOX or DOX/βCD resulted in an exponential decrease in S. aureus cell size, as well as a gradual neutralization of zeta potential. These thermodynamic profiles suggest that ion-pairing and hydrogen bonding interactions occur between DOX and the membrane of S. aureus. In addition, the adhesion of βCD to the cell membrane via hydrogen bonding is hypothesized to mediate a synergistic effect which accounts for the higher activity of DOX/βCD against S. aureus compared to pure DOX. Lower cytotoxicity and induction of osteoblast proliferation was also associated with DOX/βCD compared with free DOX. These promising findings demonstrate the potential for DOX/βCD to mediate antimicrobial activity at lower concentrations, and provides a strategy for the development of other antimicrobial formulations. |
| doi_str_mv | 10.1016/j.colsurfb.2014.01.028 |
| format | Article |
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It inhibits the activity of matrix metalloproteinases (MMPs) and affects cell proliferation. In this study, the structural and thermodynamic parameters of free DOX and a DOX/βCD complex were investigated, as well as their interactions and effects on Staphylococcus aureus cells and cellular cytotoxicity. Complexation of DOX and βCD was confirmed to be an enthalpy- and entropy-driven process, and a low equilibrium constant was obtained. Treatment of S. aureus with higher concentrations of DOX or DOX/βCD resulted in an exponential decrease in S. aureus cell size, as well as a gradual neutralization of zeta potential. These thermodynamic profiles suggest that ion-pairing and hydrogen bonding interactions occur between DOX and the membrane of S. aureus. In addition, the adhesion of βCD to the cell membrane via hydrogen bonding is hypothesized to mediate a synergistic effect which accounts for the higher activity of DOX/βCD against S. aureus compared to pure DOX. Lower cytotoxicity and induction of osteoblast proliferation was also associated with DOX/βCD compared with free DOX. These promising findings demonstrate the potential for DOX/βCD to mediate antimicrobial activity at lower concentrations, and provides a strategy for the development of other antimicrobial formulations.</description><identifier>ISSN: 0927-7765</identifier><identifier>EISSN: 1873-4367</identifier><identifier>DOI: 10.1016/j.colsurfb.2014.01.028</identifier><identifier>PMID: 24816509</identifier><language>eng</language><publisher>Netherlands</publisher><subject>Anaerobic treatment ; Animals ; Antiinfectives and antibacterials ; Bacteria ; beta-Cyclodextrins - chemistry ; beta-Cyclodextrins - pharmacology ; Calorimetry ; Cell Death - drug effects ; Cell Membrane - drug effects ; Cell Proliferation - drug effects ; Cellular ; Differential Thermal Analysis ; Doxycycline - chemistry ; Doxycycline - pharmacology ; Hydrodynamics ; Hydrogen bonding ; Light ; Magnetic Resonance Spectroscopy ; Matrix metalloproteinases ; Membranes ; Microbial Sensitivity Tests ; Osteoblasts - cytology ; Osteoblasts - drug effects ; Osteoblasts - metabolism ; Proton Magnetic Resonance Spectroscopy ; Rats, Wistar ; Scattering, Radiation ; Spectroscopy, Fourier Transform Infrared ; Staphylococcus aureus ; Staphylococcus aureus - cytology ; Staphylococcus aureus - drug effects ; Static Electricity ; Thermodynamics ; Thermogravimetry</subject><ispartof>Colloids and surfaces, B, Biointerfaces, 2014-06, Vol.118, p.194-201</ispartof><rights>Copyright © 2014. 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It inhibits the activity of matrix metalloproteinases (MMPs) and affects cell proliferation. In this study, the structural and thermodynamic parameters of free DOX and a DOX/βCD complex were investigated, as well as their interactions and effects on Staphylococcus aureus cells and cellular cytotoxicity. Complexation of DOX and βCD was confirmed to be an enthalpy- and entropy-driven process, and a low equilibrium constant was obtained. Treatment of S. aureus with higher concentrations of DOX or DOX/βCD resulted in an exponential decrease in S. aureus cell size, as well as a gradual neutralization of zeta potential. These thermodynamic profiles suggest that ion-pairing and hydrogen bonding interactions occur between DOX and the membrane of S. aureus. In addition, the adhesion of βCD to the cell membrane via hydrogen bonding is hypothesized to mediate a synergistic effect which accounts for the higher activity of DOX/βCD against S. aureus compared to pure DOX. Lower cytotoxicity and induction of osteoblast proliferation was also associated with DOX/βCD compared with free DOX. These promising findings demonstrate the potential for DOX/βCD to mediate antimicrobial activity at lower concentrations, and provides a strategy for the development of other antimicrobial formulations.</description><subject>Anaerobic treatment</subject><subject>Animals</subject><subject>Antiinfectives and antibacterials</subject><subject>Bacteria</subject><subject>beta-Cyclodextrins - chemistry</subject><subject>beta-Cyclodextrins - pharmacology</subject><subject>Calorimetry</subject><subject>Cell Death - drug effects</subject><subject>Cell Membrane - drug effects</subject><subject>Cell Proliferation - drug effects</subject><subject>Cellular</subject><subject>Differential Thermal Analysis</subject><subject>Doxycycline - chemistry</subject><subject>Doxycycline - pharmacology</subject><subject>Hydrodynamics</subject><subject>Hydrogen bonding</subject><subject>Light</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Matrix metalloproteinases</subject><subject>Membranes</subject><subject>Microbial Sensitivity Tests</subject><subject>Osteoblasts - cytology</subject><subject>Osteoblasts - drug effects</subject><subject>Osteoblasts - metabolism</subject><subject>Proton Magnetic Resonance Spectroscopy</subject><subject>Rats, Wistar</subject><subject>Scattering, Radiation</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - cytology</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Static Electricity</subject><subject>Thermodynamics</subject><subject>Thermogravimetry</subject><issn>0927-7765</issn><issn>1873-4367</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFu1DAQhi0Earelr1D5yCXp2E7s5IgqoEiVOABny7EnqldxvNiOtMsr8DY8SJ-pWbbl3NOMRv98M9JHyDWDmgGTN9vaxikvaRxqDqypgdXAuzdkwzolqkZI9ZZsoOeqUkq25-Qi5y0A8IapM3LOm47JFvoN-fO9pMWWJZmJmtnR8oApRHeYTfCW2geTjC2Y_G9TfJxpHKmL-4M92MnPePP4tzq20eG-JD_TvOySCXFCu0wmURvDbsL9P7AvmQ4n1noqYBiSmZH6eZ2s4xWe35N3o5kyXj3XS_Lz86cft3fV_bcvX28_3ldWKFWqkfe8bdF2gxg6HBEbdADCQC977kSHivUdIozIXD-AhHYQ1vLOAVrT2lZckg8n7i7FXwvmooPPFqdpfSguWTPZcM4UV-IVUa56JVTzCmrLpRKsYWyNylPUpphzwlHvkg8mHTQDfdSrt_pFrz7q1cD0qnddvH6-sQwB3f-1F5_iCYGVqTg</recordid><startdate>20140601</startdate><enddate>20140601</enddate><creator>Suárez, Diego F</creator><creator>Consuegra, Jessika</creator><creator>Trajano, Vivianne C</creator><creator>Gontijo, Sávio M L</creator><creator>Guimarães, Pedro P G</creator><creator>Cortés, Maria E</creator><creator>Denadai, Ângelo L</creator><creator>Sinisterra, Rubén D</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-3185-803X</orcidid></search><sort><creationdate>20140601</creationdate><title>Structural and thermodynamic characterization of doxycycline/β-cyclodextrin supramolecular complex and its bacterial membrane interactions</title><author>Suárez, Diego F ; Consuegra, Jessika ; Trajano, Vivianne C ; Gontijo, Sávio M L ; Guimarães, Pedro P G ; Cortés, Maria E ; Denadai, Ângelo L ; Sinisterra, Rubén D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c377t-f29255ec8b3b8efee4ed003a09692d38e7198ee0fe1d9b0605b3cc28d0eca5c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Anaerobic treatment</topic><topic>Animals</topic><topic>Antiinfectives and antibacterials</topic><topic>Bacteria</topic><topic>beta-Cyclodextrins - chemistry</topic><topic>beta-Cyclodextrins - pharmacology</topic><topic>Calorimetry</topic><topic>Cell Death - drug effects</topic><topic>Cell Membrane - drug effects</topic><topic>Cell Proliferation - drug effects</topic><topic>Cellular</topic><topic>Differential Thermal Analysis</topic><topic>Doxycycline - chemistry</topic><topic>Doxycycline - pharmacology</topic><topic>Hydrodynamics</topic><topic>Hydrogen bonding</topic><topic>Light</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Matrix metalloproteinases</topic><topic>Membranes</topic><topic>Microbial Sensitivity Tests</topic><topic>Osteoblasts - cytology</topic><topic>Osteoblasts - drug effects</topic><topic>Osteoblasts - metabolism</topic><topic>Proton Magnetic Resonance Spectroscopy</topic><topic>Rats, Wistar</topic><topic>Scattering, Radiation</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - cytology</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Static Electricity</topic><topic>Thermodynamics</topic><topic>Thermogravimetry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Suárez, Diego F</creatorcontrib><creatorcontrib>Consuegra, Jessika</creatorcontrib><creatorcontrib>Trajano, Vivianne C</creatorcontrib><creatorcontrib>Gontijo, Sávio M L</creatorcontrib><creatorcontrib>Guimarães, Pedro P G</creatorcontrib><creatorcontrib>Cortés, Maria E</creatorcontrib><creatorcontrib>Denadai, Ângelo L</creatorcontrib><creatorcontrib>Sinisterra, Rubén D</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Colloids and surfaces, B, Biointerfaces</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Suárez, Diego F</au><au>Consuegra, Jessika</au><au>Trajano, Vivianne C</au><au>Gontijo, Sávio M L</au><au>Guimarães, Pedro P G</au><au>Cortés, Maria E</au><au>Denadai, Ângelo L</au><au>Sinisterra, Rubén D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structural and thermodynamic characterization of doxycycline/β-cyclodextrin supramolecular complex and its bacterial membrane interactions</atitle><jtitle>Colloids and surfaces, B, Biointerfaces</jtitle><addtitle>Colloids Surf B Biointerfaces</addtitle><date>2014-06-01</date><risdate>2014</risdate><volume>118</volume><spage>194</spage><epage>201</epage><pages>194-201</pages><issn>0927-7765</issn><eissn>1873-4367</eissn><abstract>Doxycycline is a semi-synthetic antibiotic commonly used for the treatment of many aerobic and anaerobic bacteria. It inhibits the activity of matrix metalloproteinases (MMPs) and affects cell proliferation. In this study, the structural and thermodynamic parameters of free DOX and a DOX/βCD complex were investigated, as well as their interactions and effects on Staphylococcus aureus cells and cellular cytotoxicity. Complexation of DOX and βCD was confirmed to be an enthalpy- and entropy-driven process, and a low equilibrium constant was obtained. Treatment of S. aureus with higher concentrations of DOX or DOX/βCD resulted in an exponential decrease in S. aureus cell size, as well as a gradual neutralization of zeta potential. These thermodynamic profiles suggest that ion-pairing and hydrogen bonding interactions occur between DOX and the membrane of S. aureus. In addition, the adhesion of βCD to the cell membrane via hydrogen bonding is hypothesized to mediate a synergistic effect which accounts for the higher activity of DOX/βCD against S. aureus compared to pure DOX. Lower cytotoxicity and induction of osteoblast proliferation was also associated with DOX/βCD compared with free DOX. These promising findings demonstrate the potential for DOX/βCD to mediate antimicrobial activity at lower concentrations, and provides a strategy for the development of other antimicrobial formulations.</abstract><cop>Netherlands</cop><pmid>24816509</pmid><doi>10.1016/j.colsurfb.2014.01.028</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-3185-803X</orcidid></addata></record> |
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| subjects | Anaerobic treatment Animals Antiinfectives and antibacterials Bacteria beta-Cyclodextrins - chemistry beta-Cyclodextrins - pharmacology Calorimetry Cell Death - drug effects Cell Membrane - drug effects Cell Proliferation - drug effects Cellular Differential Thermal Analysis Doxycycline - chemistry Doxycycline - pharmacology Hydrodynamics Hydrogen bonding Light Magnetic Resonance Spectroscopy Matrix metalloproteinases Membranes Microbial Sensitivity Tests Osteoblasts - cytology Osteoblasts - drug effects Osteoblasts - metabolism Proton Magnetic Resonance Spectroscopy Rats, Wistar Scattering, Radiation Spectroscopy, Fourier Transform Infrared Staphylococcus aureus Staphylococcus aureus - cytology Staphylococcus aureus - drug effects Static Electricity Thermodynamics Thermogravimetry |
| title | Structural and thermodynamic characterization of doxycycline/β-cyclodextrin supramolecular complex and its bacterial membrane interactions |
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