Design of semisynthetic analogues and 3D-QSAR study of eunicellin-based diterpenoids as prostate cancer migration and invasion inhibitors
Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. Eunicellin-based diterpenoids are important bioactive marine natural products isolated from corals of alcyonaria species. The bioactivities of eunicellin diterpenes were correlated with their chemical str...
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| Veröffentlicht in: | European journal of medicinal chemistry 2011-04, Vol.46 (4), p.1122-1130 |
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| creator | Hassan, Hossam M. Elnagar, Ahmed Y. Khanfar, Mohammad A. Sallam, Asmaa A. Mohammed, Rabab Shaala, Lamiaa A. Youssef, Diaa T.A. Hifnawy, Mohamed S. El Sayed, Khalid A. |
| description | Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. Eunicellin-based diterpenoids are important bioactive marine natural products isolated from corals of alcyonaria species. The bioactivities of eunicellin diterpenes were correlated with their chemical structures. Recently eunicellin diterpenes from the Red Sea soft coral
Cladiella pachyclados showed significant anti-migratory and anti-invasive activities against prostate cancer in wound-healing and Cultrex
® invasion models. These results encouraged the semisynthetic and 3D-QSAR studies of this unique marine natural product class as possible hits for the control of metastatic prostate cancer. Ten new semisynthetic analogues of cladiellisin (
1) were prepared. These include C-6 carbamoylation and ∆
11−17 epoxidation. Carbamate analogues of
1 showed potent anti-migratory and anti-invasive activities against PC-3 cells. Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were performed using SYBYL 8.1 program package to create a valid 3D-QSAR model to guide future design of potent eunicellin diterpenes cancer migration inhibitors. Eunicellin-based diterpenes are potential marine natural hits appropriate for optimization as inhibitors of metastatic prostate cancer.
[Display omitted]
► Eunicellin diterpenes from marine soft coral showed significant anti-migratory and anti-invasive activities against prostate cancer. ► Ten new semisynthetic analogues of the natural product cladiellisin were prepared. ► C-6 carbamoylation and Δ
11−17 epoxidation. ► Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were conducted. |
| doi_str_mv | 10.1016/j.ejmech.2011.01.028 |
| format | Article |
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Cladiella pachyclados showed significant anti-migratory and anti-invasive activities against prostate cancer in wound-healing and Cultrex
® invasion models. These results encouraged the semisynthetic and 3D-QSAR studies of this unique marine natural product class as possible hits for the control of metastatic prostate cancer. Ten new semisynthetic analogues of cladiellisin (
1) were prepared. These include C-6 carbamoylation and ∆
11−17 epoxidation. Carbamate analogues of
1 showed potent anti-migratory and anti-invasive activities against PC-3 cells. Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were performed using SYBYL 8.1 program package to create a valid 3D-QSAR model to guide future design of potent eunicellin diterpenes cancer migration inhibitors. Eunicellin-based diterpenes are potential marine natural hits appropriate for optimization as inhibitors of metastatic prostate cancer.
[Display omitted]
► Eunicellin diterpenes from marine soft coral showed significant anti-migratory and anti-invasive activities against prostate cancer. ► Ten new semisynthetic analogues of the natural product cladiellisin were prepared. ► C-6 carbamoylation and Δ
11−17 epoxidation. ► Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were conducted.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2011.01.028</identifier><identifier>PMID: 21334794</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>3D-QSAR ; Anti-invasive ; Anti-migratory ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Cell Movement - drug effects ; Cladiellisin ; CoMFA ; CoMSIA ; Diterpenes - chemical synthesis ; Diterpenes - chemistry ; Diterpenes - pharmacology ; Drug Design ; Eunicellin diterpenoids ; General aspects ; General pharmacology ; Humans ; Inhibitory Concentration 50 ; Male ; Marine natural products ; Medical sciences ; Models, Molecular ; Molecular Conformation ; Neoplasm Invasiveness ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Prostate cancer ; Prostatic Neoplasms - pathology ; Quantitative Structure-Activity Relationship ; Urinary system</subject><ispartof>European journal of medicinal chemistry, 2011-04, Vol.46 (4), p.1122-1130</ispartof><rights>2011 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-d89e0ca50d046bb5597d4bd598f4107c39c6b68cc8d93fb4f3cad3de2b5ea3b53</citedby><cites>FETCH-LOGICAL-c391t-d89e0ca50d046bb5597d4bd598f4107c39c6b68cc8d93fb4f3cad3de2b5ea3b53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2011.01.028$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23969325$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21334794$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hassan, Hossam M.</creatorcontrib><creatorcontrib>Elnagar, Ahmed Y.</creatorcontrib><creatorcontrib>Khanfar, Mohammad A.</creatorcontrib><creatorcontrib>Sallam, Asmaa A.</creatorcontrib><creatorcontrib>Mohammed, Rabab</creatorcontrib><creatorcontrib>Shaala, Lamiaa A.</creatorcontrib><creatorcontrib>Youssef, Diaa T.A.</creatorcontrib><creatorcontrib>Hifnawy, Mohamed S.</creatorcontrib><creatorcontrib>El Sayed, Khalid A.</creatorcontrib><title>Design of semisynthetic analogues and 3D-QSAR study of eunicellin-based diterpenoids as prostate cancer migration and invasion inhibitors</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. Eunicellin-based diterpenoids are important bioactive marine natural products isolated from corals of alcyonaria species. The bioactivities of eunicellin diterpenes were correlated with their chemical structures. Recently eunicellin diterpenes from the Red Sea soft coral
Cladiella pachyclados showed significant anti-migratory and anti-invasive activities against prostate cancer in wound-healing and Cultrex
® invasion models. These results encouraged the semisynthetic and 3D-QSAR studies of this unique marine natural product class as possible hits for the control of metastatic prostate cancer. Ten new semisynthetic analogues of cladiellisin (
1) were prepared. These include C-6 carbamoylation and ∆
11−17 epoxidation. Carbamate analogues of
1 showed potent anti-migratory and anti-invasive activities against PC-3 cells. Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were performed using SYBYL 8.1 program package to create a valid 3D-QSAR model to guide future design of potent eunicellin diterpenes cancer migration inhibitors. Eunicellin-based diterpenes are potential marine natural hits appropriate for optimization as inhibitors of metastatic prostate cancer.
[Display omitted]
► Eunicellin diterpenes from marine soft coral showed significant anti-migratory and anti-invasive activities against prostate cancer. ► Ten new semisynthetic analogues of the natural product cladiellisin were prepared. ► C-6 carbamoylation and Δ
11−17 epoxidation. ► Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were conducted.</description><subject>3D-QSAR</subject><subject>Anti-invasive</subject><subject>Anti-migratory</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Movement - drug effects</subject><subject>Cladiellisin</subject><subject>CoMFA</subject><subject>CoMSIA</subject><subject>Diterpenes - chemical synthesis</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - pharmacology</subject><subject>Drug Design</subject><subject>Eunicellin diterpenoids</subject><subject>General aspects</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Male</subject><subject>Marine natural products</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Neoplasm Invasiveness</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Prostate cancer</subject><subject>Prostatic Neoplasms - pathology</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Urinary system</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kdtq3DAQhkVpaLZp36AU35ReeauD5cNNISRNWwiEnq6FDuPdWWx5K8mBfYS-deTutrkLDEiCb0bz_z8hbxhdM8rqD7s17Eaw2zWnjK1pLt4-IyvW1G0puKyekxXlXJSSi-qcvIxxRymVNaUvyDlnQlRNV63In2uIuPHF1BcRRowHn7aQ0Bba62HazBDzzRXiuvz24_J7EdPsDgsMs0cLw4C-NDqCKxwmCHvwE7rcEot9mGLSCQqrvYVQjLgJOuHk_85Df6_j8kC_RYNpCvEVOev1EOH16bwgv24-_bz6Ut7eff56dXlbWtGxVLq2A2q1pI5WtTFSdo2rjJNd21eMNhmytalba1vXid5UvbDaCQfcSNDCSHFB3h_n5g1_Z31JZdmLFO1hmqNqpeSUy6bJZHUkbdYSA_RqH3DU4aAYVUsGaqeOGaglA0Vz8Ta3vT19MJsR3P-mf6Zn4N0J0NHqoQ_ZIYyPnOjqLieYuY9HDrId9whBRYuQ3XQYwCblJnx6kwdVrKnh</recordid><startdate>20110401</startdate><enddate>20110401</enddate><creator>Hassan, Hossam M.</creator><creator>Elnagar, Ahmed Y.</creator><creator>Khanfar, Mohammad A.</creator><creator>Sallam, Asmaa A.</creator><creator>Mohammed, Rabab</creator><creator>Shaala, Lamiaa A.</creator><creator>Youssef, Diaa T.A.</creator><creator>Hifnawy, Mohamed S.</creator><creator>El Sayed, Khalid A.</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20110401</creationdate><title>Design of semisynthetic analogues and 3D-QSAR study of eunicellin-based diterpenoids as prostate cancer migration and invasion inhibitors</title><author>Hassan, Hossam M. ; Elnagar, Ahmed Y. ; Khanfar, Mohammad A. ; Sallam, Asmaa A. ; Mohammed, Rabab ; Shaala, Lamiaa A. ; Youssef, Diaa T.A. ; Hifnawy, Mohamed S. ; El Sayed, Khalid A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-d89e0ca50d046bb5597d4bd598f4107c39c6b68cc8d93fb4f3cad3de2b5ea3b53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>3D-QSAR</topic><topic>Anti-invasive</topic><topic>Anti-migratory</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Movement - drug effects</topic><topic>Cladiellisin</topic><topic>CoMFA</topic><topic>CoMSIA</topic><topic>Diterpenes - chemical synthesis</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - pharmacology</topic><topic>Drug Design</topic><topic>Eunicellin diterpenoids</topic><topic>General aspects</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Male</topic><topic>Marine natural products</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Neoplasm Invasiveness</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Prostate cancer</topic><topic>Prostatic Neoplasms - pathology</topic><topic>Quantitative Structure-Activity Relationship</topic><topic>Urinary system</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hassan, Hossam M.</creatorcontrib><creatorcontrib>Elnagar, Ahmed Y.</creatorcontrib><creatorcontrib>Khanfar, Mohammad A.</creatorcontrib><creatorcontrib>Sallam, Asmaa A.</creatorcontrib><creatorcontrib>Mohammed, Rabab</creatorcontrib><creatorcontrib>Shaala, Lamiaa A.</creatorcontrib><creatorcontrib>Youssef, Diaa T.A.</creatorcontrib><creatorcontrib>Hifnawy, Mohamed S.</creatorcontrib><creatorcontrib>El Sayed, Khalid A.</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hassan, Hossam M.</au><au>Elnagar, Ahmed Y.</au><au>Khanfar, Mohammad A.</au><au>Sallam, Asmaa A.</au><au>Mohammed, Rabab</au><au>Shaala, Lamiaa A.</au><au>Youssef, Diaa T.A.</au><au>Hifnawy, Mohamed S.</au><au>El Sayed, Khalid A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design of semisynthetic analogues and 3D-QSAR study of eunicellin-based diterpenoids as prostate cancer migration and invasion inhibitors</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2011-04-01</date><risdate>2011</risdate><volume>46</volume><issue>4</issue><spage>1122</spage><epage>1130</epage><pages>1122-1130</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. Eunicellin-based diterpenoids are important bioactive marine natural products isolated from corals of alcyonaria species. The bioactivities of eunicellin diterpenes were correlated with their chemical structures. Recently eunicellin diterpenes from the Red Sea soft coral
Cladiella pachyclados showed significant anti-migratory and anti-invasive activities against prostate cancer in wound-healing and Cultrex
® invasion models. These results encouraged the semisynthetic and 3D-QSAR studies of this unique marine natural product class as possible hits for the control of metastatic prostate cancer. Ten new semisynthetic analogues of cladiellisin (
1) were prepared. These include C-6 carbamoylation and ∆
11−17 epoxidation. Carbamate analogues of
1 showed potent anti-migratory and anti-invasive activities against PC-3 cells. Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were performed using SYBYL 8.1 program package to create a valid 3D-QSAR model to guide future design of potent eunicellin diterpenes cancer migration inhibitors. Eunicellin-based diterpenes are potential marine natural hits appropriate for optimization as inhibitors of metastatic prostate cancer.
[Display omitted]
► Eunicellin diterpenes from marine soft coral showed significant anti-migratory and anti-invasive activities against prostate cancer. ► Ten new semisynthetic analogues of the natural product cladiellisin were prepared. ► C-6 carbamoylation and Δ
11−17 epoxidation. ► Comparative Molecular Field Analysis (CoMFA) and Comparative Molecular Similarity Indices Analysis (CoMSIA) were conducted.</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>21334794</pmid><doi>10.1016/j.ejmech.2011.01.028</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | European journal of medicinal chemistry, 2011-04, Vol.46 (4), p.1122-1130 |
| issn | 0223-5234 1768-3254 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | 3D-QSAR Anti-invasive Anti-migratory Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line, Tumor Cell Movement - drug effects Cladiellisin CoMFA CoMSIA Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - pharmacology Drug Design Eunicellin diterpenoids General aspects General pharmacology Humans Inhibitory Concentration 50 Male Marine natural products Medical sciences Models, Molecular Molecular Conformation Neoplasm Invasiveness Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Prostate cancer Prostatic Neoplasms - pathology Quantitative Structure-Activity Relationship Urinary system |
| title | Design of semisynthetic analogues and 3D-QSAR study of eunicellin-based diterpenoids as prostate cancer migration and invasion inhibitors |
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