Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions
Residues of pharmaceutical antibiotics are found in the environment, whose fate and effects are governed by sorption. Thus, the extent and mechanisms of the soil sorption of p-aminobenzoic acid and five sulfonamide antibiotics (sulfanilamide, sulfadimidine, sulfadiazine, sulfadimethoxine, and sulfap...
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| Veröffentlicht in: | Journal of environmental quality 2004-07, Vol.33 (4), p.1331-1342 |
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| description | Residues of pharmaceutical antibiotics are found in the environment, whose fate and effects are governed by sorption. Thus, the extent and mechanisms of the soil sorption of p-aminobenzoic acid and five sulfonamide antibiotics (sulfanilamide, sulfadimidine, sulfadiazine, sulfadimethoxine, and sulfapyridine) were investigated using topsoils of fertilized and unfertilized Chernozem and their organic-mineral particle-size fractions. Freundlich adsorption coefficients (Kf) ranged from 0.5 to 6.5. Adsorption increased with aromaticity and electronegativity of functional groups attached to the sulfonyl-phenylamine core. Adsorption to soil and particle-size fractions increased in the sequence: coarse silt < whole soil < medium silt < sand < clay < fine silt and was influenced by pH. Sorption nonlinearity (1/n < = 0.76) indicated specific interactions with functional groups of soil organic matter (SOM). Phenolic and carboxylic groups, N-heterocyclic compounds, and lignin decomposition products were tentatively assigned as preferred binding sites using statistical analysis of pyrolysis¡mass spectra and adsorption coefficients. Adsorption of sulfonamides to mineral soil colloids was weaker and resulted in a stronger desorption from clay-size fractions. Moreover, steric accessibility of organic¡mineral complexes in clay-size fractions was significantly reduced. With a quantitative structure¡property relationship (QSPR) model, combining the organic carbon concentration, the sulfonamides' chromatographic capacity factor (k'), and nondissociated species concentration (CFa), distribution coefficients (Kd) were estimated with a cross-validated regression coefficient Q2 = 0.71. Modeling and molecular mechanics calculations of antibiotic-SOM complexes showed preferred site-specific sorption via hydrogen bonds and van der Waals interactions. Distinct chemical structural properties, such as aromaticity and van der Waals volumes, correlated with the sorption data. |
| doi_str_mv | 10.2134/jeq2004.1331 |
| format | Article |
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Thus, the extent and mechanisms of the soil sorption of p-aminobenzoic acid and five sulfonamide antibiotics (sulfanilamide, sulfadimidine, sulfadiazine, sulfadimethoxine, and sulfapyridine) were investigated using topsoils of fertilized and unfertilized Chernozem and their organic-mineral particle-size fractions. Freundlich adsorption coefficients (Kf) ranged from 0.5 to 6.5. Adsorption increased with aromaticity and electronegativity of functional groups attached to the sulfonyl-phenylamine core. Adsorption to soil and particle-size fractions increased in the sequence: coarse silt < whole soil < medium silt < sand < clay < fine silt and was influenced by pH. Sorption nonlinearity (1/n < = 0.76) indicated specific interactions with functional groups of soil organic matter (SOM). Phenolic and carboxylic groups, N-heterocyclic compounds, and lignin decomposition products were tentatively assigned as preferred binding sites using statistical analysis of pyrolysis¡mass spectra and adsorption coefficients. Adsorption of sulfonamides to mineral soil colloids was weaker and resulted in a stronger desorption from clay-size fractions. Moreover, steric accessibility of organic¡mineral complexes in clay-size fractions was significantly reduced. With a quantitative structure¡property relationship (QSPR) model, combining the organic carbon concentration, the sulfonamides' chromatographic capacity factor (k'), and nondissociated species concentration (CFa), distribution coefficients (Kd) were estimated with a cross-validated regression coefficient Q2 = 0.71. Modeling and molecular mechanics calculations of antibiotic-SOM complexes showed preferred site-specific sorption via hydrogen bonds and van der Waals interactions. Distinct chemical structural properties, such as aromaticity and van der Waals volumes, correlated with the sorption data.]]></description><identifier>ISSN: 0047-2425</identifier><identifier>EISSN: 1537-2537</identifier><identifier>DOI: 10.2134/jeq2004.1331</identifier><identifier>PMID: 15254115</identifier><identifier>CODEN: JEVQAA</identifier><language>eng</language><publisher>Madison: American Society of Agronomy, Crop Science Society of America, Soil Science Society</publisher><subject>Adsorption ; Agronomy. Soil science and plant productions ; aminobenzoic acids ; Anti-Infective Agents - analysis ; Anti-Infective Agents - chemistry ; antibiotic residues ; Antibiotics ; Applied sciences ; binding sites ; Biological and medical sciences ; chemical structure ; Clay ; Comparative studies ; Earth sciences ; Earth, ocean, space ; Engineering and environment geology. Geothermics ; Environmental impact ; Environmental Monitoring ; Exact sciences and technology ; fertilizer application ; Fertilizers ; Fundamental and applied biological sciences. Psychology ; Hapludolls ; high performance liquid chromatography ; loess soils ; Mass spectra ; mass spectrometry ; mathematical models ; Models, Theoretical ; Organic carbon ; Organic matter ; p-aminobenzoic acid ; Particle Size ; Phenols ; Pollution ; Pollution, environment geology ; Pyrolysis ; Silt ; Soil adsorption ; soil chemical properties ; Soil organic matter ; soil physical properties ; Soil Pollutants - analysis ; soil pollution ; soil stabilization ; soil texture ; Soils ; Sorption ; Statistical analysis ; sulfadiazine ; sulfadimethazine ; sulfadimethoxine ; sulfanilamide ; sulfapyridine ; Sulfide compounds ; sulfonamides ; Sulfonamides - analysis ; Sulfonamides - chemistry ; Topsoil</subject><ispartof>Journal of environmental quality, 2004-07, Vol.33 (4), p.1331-1342</ispartof><rights>ASA, CSSA, SSSA</rights><rights>2004 INIST-CNRS</rights><rights>Copyright American Society of Agronomy Jul/Aug 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a6641-32fd445865db717c4bb7640772cc4fd5c65508a1f9f0f251b0318592f32393df3</citedby><cites>FETCH-LOGICAL-a6641-32fd445865db717c4bb7640772cc4fd5c65508a1f9f0f251b0318592f32393df3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.2134%2Fjeq2004.1331$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.2134%2Fjeq2004.1331$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15962403$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15254115$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thiele-Bruhn, S</creatorcontrib><creatorcontrib>Seibicke, T</creatorcontrib><creatorcontrib>Schulten, H.R</creatorcontrib><creatorcontrib>Leinweber, P</creatorcontrib><title>Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions</title><title>Journal of environmental quality</title><addtitle>J Environ Qual</addtitle><description><![CDATA[Residues of pharmaceutical antibiotics are found in the environment, whose fate and effects are governed by sorption. Thus, the extent and mechanisms of the soil sorption of p-aminobenzoic acid and five sulfonamide antibiotics (sulfanilamide, sulfadimidine, sulfadiazine, sulfadimethoxine, and sulfapyridine) were investigated using topsoils of fertilized and unfertilized Chernozem and their organic-mineral particle-size fractions. Freundlich adsorption coefficients (Kf) ranged from 0.5 to 6.5. Adsorption increased with aromaticity and electronegativity of functional groups attached to the sulfonyl-phenylamine core. Adsorption to soil and particle-size fractions increased in the sequence: coarse silt < whole soil < medium silt < sand < clay < fine silt and was influenced by pH. Sorption nonlinearity (1/n < = 0.76) indicated specific interactions with functional groups of soil organic matter (SOM). Phenolic and carboxylic groups, N-heterocyclic compounds, and lignin decomposition products were tentatively assigned as preferred binding sites using statistical analysis of pyrolysis¡mass spectra and adsorption coefficients. Adsorption of sulfonamides to mineral soil colloids was weaker and resulted in a stronger desorption from clay-size fractions. Moreover, steric accessibility of organic¡mineral complexes in clay-size fractions was significantly reduced. With a quantitative structure¡property relationship (QSPR) model, combining the organic carbon concentration, the sulfonamides' chromatographic capacity factor (k'), and nondissociated species concentration (CFa), distribution coefficients (Kd) were estimated with a cross-validated regression coefficient Q2 = 0.71. Modeling and molecular mechanics calculations of antibiotic-SOM complexes showed preferred site-specific sorption via hydrogen bonds and van der Waals interactions. Distinct chemical structural properties, such as aromaticity and van der Waals volumes, correlated with the sorption data.]]></description><subject>Adsorption</subject><subject>Agronomy. Soil science and plant productions</subject><subject>aminobenzoic acids</subject><subject>Anti-Infective Agents - analysis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>antibiotic residues</subject><subject>Antibiotics</subject><subject>Applied sciences</subject><subject>binding sites</subject><subject>Biological and medical sciences</subject><subject>chemical structure</subject><subject>Clay</subject><subject>Comparative studies</subject><subject>Earth sciences</subject><subject>Earth, ocean, space</subject><subject>Engineering and environment geology. Geothermics</subject><subject>Environmental impact</subject><subject>Environmental Monitoring</subject><subject>Exact sciences and technology</subject><subject>fertilizer application</subject><subject>Fertilizers</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hapludolls</subject><subject>high performance liquid chromatography</subject><subject>loess soils</subject><subject>Mass spectra</subject><subject>mass spectrometry</subject><subject>mathematical models</subject><subject>Models, Theoretical</subject><subject>Organic carbon</subject><subject>Organic matter</subject><subject>p-aminobenzoic acid</subject><subject>Particle Size</subject><subject>Phenols</subject><subject>Pollution</subject><subject>Pollution, environment geology</subject><subject>Pyrolysis</subject><subject>Silt</subject><subject>Soil adsorption</subject><subject>soil chemical properties</subject><subject>Soil organic matter</subject><subject>soil physical properties</subject><subject>Soil Pollutants - analysis</subject><subject>soil pollution</subject><subject>soil stabilization</subject><subject>soil texture</subject><subject>Soils</subject><subject>Sorption</subject><subject>Statistical analysis</subject><subject>sulfadiazine</subject><subject>sulfadimethazine</subject><subject>sulfadimethoxine</subject><subject>sulfanilamide</subject><subject>sulfapyridine</subject><subject>Sulfide compounds</subject><subject>sulfonamides</subject><subject>Sulfonamides - analysis</subject><subject>Sulfonamides - chemistry</subject><subject>Topsoil</subject><issn>0047-2425</issn><issn>1537-2537</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>8G5</sourceid><sourceid>BEC</sourceid><sourceid>BENPR</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNqFkUtv1DAUhS0EokNhxxoiJFiR4utHHC9RVV6qhFDpElmOY1OPknhqT1SVX8-NJhKIBbPw6_rz8dU5hDwHesaAi3dbf8soFWfAOTwgG5Bc1Qynh2SDZdwLJk_Ik1K2lAKjqnlMTkAyKQDkhvy4Snm3j2mqUqjKPIQ02TH2vtrd2Dxa5-d9dHao7LSPXUx4KBXCdzdp8FVJcSh41Vc7m_Fq8HWJv3wVsnWLZnlKHgU7FP9sXU_J9YeL7-ef6suvHz-fv7-sbdMIqDkLvRCybWTfKVBOdJ1qBFWKOSdCL10jJW0tBB1oYBI6yqGVmgXOuOZ94KfkzUF3l9Pt7MvejLE4Pwx28mkuhjfoiFb8KMgAUFG3R0FooFVa0uOgUBTNFgi--gfcpjlPaIsBbE2DYgyhtwfI5VRK9sHschxtvjdAzRK3WeM2S9yIv1g15270_R94zReB1ytgC8aIwUwulr843TBBF1_0gbuLg7__76fmy8U3tgwsrE28PLwNNhn7M6P-9RWjwCnVgnHa8t8Mr8sI</recordid><startdate>200407</startdate><enddate>200407</enddate><creator>Thiele-Bruhn, S</creator><creator>Seibicke, T</creator><creator>Schulten, H.R</creator><creator>Leinweber, P</creator><general>American Society of Agronomy, Crop Science Society of America, Soil Science Society</general><general>Crop Science Society of America</general><general>American Society of Agronomy</general><scope>FBQ</scope><scope>IQODW</scope><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>3V.</scope><scope>7ST</scope><scope>7T7</scope><scope>7TG</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8AF</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KL.</scope><scope>L6V</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>M2P</scope><scope>M7S</scope><scope>MBDVC</scope><scope>P64</scope><scope>PATMY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>Q9U</scope><scope>S0X</scope><scope>SOI</scope><scope>7TV</scope><scope>KR7</scope></search><sort><creationdate>200407</creationdate><title>Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions</title><author>Thiele-Bruhn, S ; Seibicke, T ; Schulten, H.R ; Leinweber, P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a6641-32fd445865db717c4bb7640772cc4fd5c65508a1f9f0f251b0318592f32393df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Adsorption</topic><topic>Agronomy. Soil science and plant productions</topic><topic>aminobenzoic acids</topic><topic>Anti-Infective Agents - analysis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>antibiotic residues</topic><topic>Antibiotics</topic><topic>Applied sciences</topic><topic>binding sites</topic><topic>Biological and medical sciences</topic><topic>chemical structure</topic><topic>Clay</topic><topic>Comparative studies</topic><topic>Earth sciences</topic><topic>Earth, ocean, space</topic><topic>Engineering and environment geology. Geothermics</topic><topic>Environmental impact</topic><topic>Environmental Monitoring</topic><topic>Exact sciences and technology</topic><topic>fertilizer application</topic><topic>Fertilizers</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hapludolls</topic><topic>high performance liquid chromatography</topic><topic>loess soils</topic><topic>Mass spectra</topic><topic>mass spectrometry</topic><topic>mathematical models</topic><topic>Models, Theoretical</topic><topic>Organic carbon</topic><topic>Organic matter</topic><topic>p-aminobenzoic acid</topic><topic>Particle Size</topic><topic>Phenols</topic><topic>Pollution</topic><topic>Pollution, environment geology</topic><topic>Pyrolysis</topic><topic>Silt</topic><topic>Soil adsorption</topic><topic>soil chemical properties</topic><topic>Soil organic matter</topic><topic>soil physical properties</topic><topic>Soil Pollutants - analysis</topic><topic>soil pollution</topic><topic>soil stabilization</topic><topic>soil texture</topic><topic>Soils</topic><topic>Sorption</topic><topic>Statistical analysis</topic><topic>sulfadiazine</topic><topic>sulfadimethazine</topic><topic>sulfadimethoxine</topic><topic>sulfanilamide</topic><topic>sulfapyridine</topic><topic>Sulfide compounds</topic><topic>sulfonamides</topic><topic>Sulfonamides - 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Thus, the extent and mechanisms of the soil sorption of p-aminobenzoic acid and five sulfonamide antibiotics (sulfanilamide, sulfadimidine, sulfadiazine, sulfadimethoxine, and sulfapyridine) were investigated using topsoils of fertilized and unfertilized Chernozem and their organic-mineral particle-size fractions. Freundlich adsorption coefficients (Kf) ranged from 0.5 to 6.5. Adsorption increased with aromaticity and electronegativity of functional groups attached to the sulfonyl-phenylamine core. Adsorption to soil and particle-size fractions increased in the sequence: coarse silt < whole soil < medium silt < sand < clay < fine silt and was influenced by pH. Sorption nonlinearity (1/n < = 0.76) indicated specific interactions with functional groups of soil organic matter (SOM). Phenolic and carboxylic groups, N-heterocyclic compounds, and lignin decomposition products were tentatively assigned as preferred binding sites using statistical analysis of pyrolysis¡mass spectra and adsorption coefficients. Adsorption of sulfonamides to mineral soil colloids was weaker and resulted in a stronger desorption from clay-size fractions. Moreover, steric accessibility of organic¡mineral complexes in clay-size fractions was significantly reduced. With a quantitative structure¡property relationship (QSPR) model, combining the organic carbon concentration, the sulfonamides' chromatographic capacity factor (k'), and nondissociated species concentration (CFa), distribution coefficients (Kd) were estimated with a cross-validated regression coefficient Q2 = 0.71. Modeling and molecular mechanics calculations of antibiotic-SOM complexes showed preferred site-specific sorption via hydrogen bonds and van der Waals interactions. Distinct chemical structural properties, such as aromaticity and van der Waals volumes, correlated with the sorption data.]]></abstract><cop>Madison</cop><pub>American Society of Agronomy, Crop Science Society of America, Soil Science Society</pub><pmid>15254115</pmid><doi>10.2134/jeq2004.1331</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0047-2425 |
| ispartof | Journal of environmental quality, 2004-07, Vol.33 (4), p.1331-1342 |
| issn | 0047-2425 1537-2537 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_36253973 |
| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Adsorption Agronomy. Soil science and plant productions aminobenzoic acids Anti-Infective Agents - analysis Anti-Infective Agents - chemistry antibiotic residues Antibiotics Applied sciences binding sites Biological and medical sciences chemical structure Clay Comparative studies Earth sciences Earth, ocean, space Engineering and environment geology. Geothermics Environmental impact Environmental Monitoring Exact sciences and technology fertilizer application Fertilizers Fundamental and applied biological sciences. Psychology Hapludolls high performance liquid chromatography loess soils Mass spectra mass spectrometry mathematical models Models, Theoretical Organic carbon Organic matter p-aminobenzoic acid Particle Size Phenols Pollution Pollution, environment geology Pyrolysis Silt Soil adsorption soil chemical properties Soil organic matter soil physical properties Soil Pollutants - analysis soil pollution soil stabilization soil texture Soils Sorption Statistical analysis sulfadiazine sulfadimethazine sulfadimethoxine sulfanilamide sulfapyridine Sulfide compounds sulfonamides Sulfonamides - analysis Sulfonamides - chemistry Topsoil |
| title | Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T21%3A12%3A30IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sorption%20of%20sulfonamide%20pharmaceutical%20antibiotics%20on%20whole%20soils%20and%20particle-size%20fractions&rft.jtitle=Journal%20of%20environmental%20quality&rft.au=Thiele-Bruhn,%20S&rft.date=2004-07&rft.volume=33&rft.issue=4&rft.spage=1331&rft.epage=1342&rft.pages=1331-1342&rft.issn=0047-2425&rft.eissn=1537-2537&rft.coden=JEVQAA&rft_id=info:doi/10.2134/jeq2004.1331&rft_dat=%3Cproquest_cross%3E14702544%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=197391722&rft_id=info:pmid/15254115&rfr_iscdi=true |