Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata
Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C ( 1) and chalcone derivatives ( 2– 6) from the methanol extract of Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2006-03, Vol.14 (6), p.1710-1714 |
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| creator | Cheenpracha, Sarot Karalai, Chatchanok Ponglimanont, Chanita Subhadhirasakul, Sanan Tewtrakul, Supinya |
| description | Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas others exhibited mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity.
Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas other compounds exhibited only mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity. As regards active constituents contained in
B. pandurata rhizomes, hydroxypanduratin A (
3) and panduratin A (
2) are active principles against HIV-1 PR. |
| doi_str_mv | 10.1016/j.bmc.2005.10.019 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67648682</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089605009892</els_id><sourcerecordid>17078617</sourcerecordid><originalsourceid>FETCH-LOGICAL-c478t-837d55daae9fd775cb1dc9ba7c5a67a009ca228bf8d9fa441fdf63dac5f981ae3</originalsourceid><addsrcrecordid>eNqFkMtKBDEQRYMoOj4-wI30Rnc9Jv3IA1cq4wMEN-o2VCcVyTDdGZPuAf_ebmbAna6KKs4tLoeQc0bnjDJ-vZw3rZkXlNbjPqdM7ZEZq3iVl6Vi-2RGFZc5lYofkeOUlpTSolLskBwxXvCyUHJGFrdd7_On54-cZesYeoSEGZjeb3z_nQWXmdCuw9DZlLkY2uwuYMKuwfjpIVtDZ4cIPZySAwerhGe7eULeHxZv90_5y-vj8_3tS24qIftclsLWtQVA5awQtWmYNaoBYWrgAihVBopCNk5a5aCqmLOOlxZM7ZRkgOUJudr-Hat-DZh63fpkcLWCDsOQNBe8klwW_4JMUCE5EyPItqCJIaWITq-jbyF-a0b1JFkv9ShZT5Kn0yh5zFzsng9Ni_Y3sbM6Apc7AJKBlYvQGZ9-OVFLToup5c2Ww9HZxmPUyXjsDFof0fTaBv9HjR8gfZog</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17078617</pqid></control><display><type>article</type><title>Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Cheenpracha, Sarot ; Karalai, Chatchanok ; Ponglimanont, Chanita ; Subhadhirasakul, Sanan ; Tewtrakul, Supinya</creator><creatorcontrib>Cheenpracha, Sarot ; Karalai, Chatchanok ; Ponglimanont, Chanita ; Subhadhirasakul, Sanan ; Tewtrakul, Supinya</creatorcontrib><description>Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas others exhibited mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity.
Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas other compounds exhibited only mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity. As regards active constituents contained in
B. pandurata rhizomes, hydroxypanduratin A (
3) and panduratin A (
2) are active principles against HIV-1 PR.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2005.10.019</identifier><identifier>PMID: 16263298</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Biological and medical sciences ; Boesenbergia pandurata ; Chalcones - chemistry ; Chalcones - isolation & purification ; Chalcones - pharmacology ; Cyclohexenyl chalcone derivatives ; Drug Evaluation, Preclinical ; General pharmacology ; HIV Protease - chemistry ; HIV Protease - drug effects ; HIV Protease Inhibitors - chemistry ; HIV Protease Inhibitors - isolation & purification ; HIV Protease Inhibitors - pharmacology ; HIV-1 - enzymology ; HIV-1 protease ; Human immunodeficiency virus 1 ; Medical sciences ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plant Extracts - chemistry ; Plant Roots - chemistry ; Plants, Medicinal ; Structure-Activity Relationship ; Zingiberaceae - chemistry</subject><ispartof>Bioorganic & medicinal chemistry, 2006-03, Vol.14 (6), p.1710-1714</ispartof><rights>2005 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c478t-837d55daae9fd775cb1dc9ba7c5a67a009ca228bf8d9fa441fdf63dac5f981ae3</citedby><cites>FETCH-LOGICAL-c478t-837d55daae9fd775cb1dc9ba7c5a67a009ca228bf8d9fa441fdf63dac5f981ae3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2005.10.019$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17586022$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16263298$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cheenpracha, Sarot</creatorcontrib><creatorcontrib>Karalai, Chatchanok</creatorcontrib><creatorcontrib>Ponglimanont, Chanita</creatorcontrib><creatorcontrib>Subhadhirasakul, Sanan</creatorcontrib><creatorcontrib>Tewtrakul, Supinya</creatorcontrib><title>Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas others exhibited mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity.
Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas other compounds exhibited only mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity. As regards active constituents contained in
B. pandurata rhizomes, hydroxypanduratin A (
3) and panduratin A (
2) are active principles against HIV-1 PR.</description><subject>Biological and medical sciences</subject><subject>Boesenbergia pandurata</subject><subject>Chalcones - chemistry</subject><subject>Chalcones - isolation & purification</subject><subject>Chalcones - pharmacology</subject><subject>Cyclohexenyl chalcone derivatives</subject><subject>Drug Evaluation, Preclinical</subject><subject>General pharmacology</subject><subject>HIV Protease - chemistry</subject><subject>HIV Protease - drug effects</subject><subject>HIV Protease Inhibitors - chemistry</subject><subject>HIV Protease Inhibitors - isolation & purification</subject><subject>HIV Protease Inhibitors - pharmacology</subject><subject>HIV-1 - enzymology</subject><subject>HIV-1 protease</subject><subject>Human immunodeficiency virus 1</subject><subject>Medical sciences</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Roots - chemistry</subject><subject>Plants, Medicinal</subject><subject>Structure-Activity Relationship</subject><subject>Zingiberaceae - chemistry</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMtKBDEQRYMoOj4-wI30Rnc9Jv3IA1cq4wMEN-o2VCcVyTDdGZPuAf_ebmbAna6KKs4tLoeQc0bnjDJ-vZw3rZkXlNbjPqdM7ZEZq3iVl6Vi-2RGFZc5lYofkeOUlpTSolLskBwxXvCyUHJGFrdd7_On54-cZesYeoSEGZjeb3z_nQWXmdCuw9DZlLkY2uwuYMKuwfjpIVtDZ4cIPZySAwerhGe7eULeHxZv90_5y-vj8_3tS24qIftclsLWtQVA5awQtWmYNaoBYWrgAihVBopCNk5a5aCqmLOOlxZM7ZRkgOUJudr-Hat-DZh63fpkcLWCDsOQNBe8klwW_4JMUCE5EyPItqCJIaWITq-jbyF-a0b1JFkv9ShZT5Kn0yh5zFzsng9Ni_Y3sbM6Apc7AJKBlYvQGZ9-OVFLToup5c2Ww9HZxmPUyXjsDFof0fTaBv9HjR8gfZog</recordid><startdate>20060315</startdate><enddate>20060315</enddate><creator>Cheenpracha, Sarot</creator><creator>Karalai, Chatchanok</creator><creator>Ponglimanont, Chanita</creator><creator>Subhadhirasakul, Sanan</creator><creator>Tewtrakul, Supinya</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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>7QO</scope><scope>7U9</scope><scope>8FD</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20060315</creationdate><title>Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata</title><author>Cheenpracha, Sarot ; Karalai, Chatchanok ; Ponglimanont, Chanita ; Subhadhirasakul, Sanan ; Tewtrakul, Supinya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c478t-837d55daae9fd775cb1dc9ba7c5a67a009ca228bf8d9fa441fdf63dac5f981ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Biological and medical sciences</topic><topic>Boesenbergia pandurata</topic><topic>Chalcones - chemistry</topic><topic>Chalcones - isolation & purification</topic><topic>Chalcones - pharmacology</topic><topic>Cyclohexenyl chalcone derivatives</topic><topic>Drug Evaluation, Preclinical</topic><topic>General pharmacology</topic><topic>HIV Protease - chemistry</topic><topic>HIV Protease - drug effects</topic><topic>HIV Protease Inhibitors - chemistry</topic><topic>HIV Protease Inhibitors - isolation & purification</topic><topic>HIV Protease Inhibitors - pharmacology</topic><topic>HIV-1 - enzymology</topic><topic>HIV-1 protease</topic><topic>Human immunodeficiency virus 1</topic><topic>Medical sciences</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Roots - chemistry</topic><topic>Plants, Medicinal</topic><topic>Structure-Activity Relationship</topic><topic>Zingiberaceae - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cheenpracha, Sarot</creatorcontrib><creatorcontrib>Karalai, Chatchanok</creatorcontrib><creatorcontrib>Ponglimanont, Chanita</creatorcontrib><creatorcontrib>Subhadhirasakul, Sanan</creatorcontrib><creatorcontrib>Tewtrakul, Supinya</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cheenpracha, Sarot</au><au>Karalai, Chatchanok</au><au>Ponglimanont, Chanita</au><au>Subhadhirasakul, Sanan</au><au>Tewtrakul, Supinya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2006-03-15</date><risdate>2006</risdate><volume>14</volume><issue>6</issue><spage>1710</spage><epage>1714</epage><pages>1710-1714</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas others exhibited mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity.
Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (
1) and chalcone derivatives (
2–
6) from the methanol extract of
Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (
2), hydroxypanduratin A (
3), helichrysetin (
4), 2′,4′,6′-trihydroxyhydrochalcone (
5), and uvangoletin (
6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that
3 possessed the most potent anti-HIV-1 PR activity with an IC
50 value of 5.6
μM, followed by
2 (IC
50
=
18.7
μM), whereas other compounds exhibited only mild activity. Structure–activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4‴ reduced activity; and (4) introduction of double bond at C1′ and C6′ of chalcone gave higher activity. As regards active constituents contained in
B. pandurata rhizomes, hydroxypanduratin A (
3) and panduratin A (
2) are active principles against HIV-1 PR.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16263298</pmid><doi>10.1016/j.bmc.2005.10.019</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry, 2006-03, Vol.14 (6), p.1710-1714 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Biological and medical sciences Boesenbergia pandurata Chalcones - chemistry Chalcones - isolation & purification Chalcones - pharmacology Cyclohexenyl chalcone derivatives Drug Evaluation, Preclinical General pharmacology HIV Protease - chemistry HIV Protease - drug effects HIV Protease Inhibitors - chemistry HIV Protease Inhibitors - isolation & purification HIV Protease Inhibitors - pharmacology HIV-1 - enzymology HIV-1 protease Human immunodeficiency virus 1 Medical sciences Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plant Extracts - chemistry Plant Roots - chemistry Plants, Medicinal Structure-Activity Relationship Zingiberaceae - chemistry |
| title | Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata |
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