Synthesis of BDNF-mimetic dimeric dipeptide GSB-106, a potential neuroprotector drug
The BDNF-mimetic dimeric dipeptide bis -( N -monosuccinyl-L-seryl-L-lysine) hexamethylenediamide (GSB-106) based on the structure of beta-turn loop 4 (BDNF-Asp 93 -Ser 94 -Lys 95 -Lys 96 -) was synthesized. GSB-106 showed neuroprotective activity in vitro at concentrations 10 –6 -10 –8 M and antidep...
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| Veröffentlicht in: | Pharmaceutical chemistry journal 2013-04, Vol.47 (1), p.20-27 |
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| creator | Tarasyuk, A. V. Pomogaibo, S. V. Kurilov, D. V. Gudasheva, T. A. |
| description | The BDNF-mimetic dimeric dipeptide
bis
-(
N
-monosuccinyl-L-seryl-L-lysine) hexamethylenediamide (GSB-106) based on the structure of beta-turn loop 4 (BDNF-Asp
93
-Ser
94
-Lys
95
-Lys
96
-) was synthesized. GSB-106 showed neuroprotective activity
in vitro
at concentrations 10
–6
-10
–8
M and antidepressant activity
in vivo
in rats at i.p. injected doses of 0.1-1 mg/kg. The target peptide GSB-106 was obtained using three schemes in order to select the optimum synthetic pathway. The first scheme was based on the strategy of Boc/Z protecting groups using the method of pentafluorophenyl esters. The second scheme also used the Boc/Z strategy and the
N
-hydroxysuccinimide ester method. The third scheme used the Z/Boc strategy and the azide method. These three methods for synthesizing GSB-106 were compared with respect to yield and optical purity. The optimum result was obtained by using the third scheme that involved Z/Boc protecting groups and the azide method of peptide bond formation. |
| doi_str_mv | 10.1007/s11094-013-0888-3 |
| format | Article |
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bis
-(
N
-monosuccinyl-L-seryl-L-lysine) hexamethylenediamide (GSB-106) based on the structure of beta-turn loop 4 (BDNF-Asp
93
-Ser
94
-Lys
95
-Lys
96
-) was synthesized. GSB-106 showed neuroprotective activity
in vitro
at concentrations 10
–6
-10
–8
M and antidepressant activity
in vivo
in rats at i.p. injected doses of 0.1-1 mg/kg. The target peptide GSB-106 was obtained using three schemes in order to select the optimum synthetic pathway. The first scheme was based on the strategy of Boc/Z protecting groups using the method of pentafluorophenyl esters. The second scheme also used the Boc/Z strategy and the
N
-hydroxysuccinimide ester method. The third scheme used the Z/Boc strategy and the azide method. These three methods for synthesizing GSB-106 were compared with respect to yield and optical purity. The optimum result was obtained by using the third scheme that involved Z/Boc protecting groups and the azide method of peptide bond formation.</description><identifier>ISSN: 0091-150X</identifier><identifier>EISSN: 1573-9031</identifier><identifier>DOI: 10.1007/s11094-013-0888-3</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Amino acids ; Antidepressants ; Esters ; Medicine ; Organic Chemistry ; Peptides ; Pharmacology/Toxicology ; Pharmacy</subject><ispartof>Pharmaceutical chemistry journal, 2013-04, Vol.47 (1), p.20-27</ispartof><rights>Springer Science+Business Media New York 2013</rights><rights>COPYRIGHT 2013 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c355t-546d92113b2ed3b57c040192c0845add40e181c8ec6990753b0af05746e8de183</citedby><cites>FETCH-LOGICAL-c355t-546d92113b2ed3b57c040192c0845add40e181c8ec6990753b0af05746e8de183</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11094-013-0888-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11094-013-0888-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27922,27923,41486,42555,51317</link.rule.ids></links><search><creatorcontrib>Tarasyuk, A. V.</creatorcontrib><creatorcontrib>Pomogaibo, S. V.</creatorcontrib><creatorcontrib>Kurilov, D. V.</creatorcontrib><creatorcontrib>Gudasheva, T. A.</creatorcontrib><title>Synthesis of BDNF-mimetic dimeric dipeptide GSB-106, a potential neuroprotector drug</title><title>Pharmaceutical chemistry journal</title><addtitle>Pharm Chem J</addtitle><description>The BDNF-mimetic dimeric dipeptide
bis
-(
N
-monosuccinyl-L-seryl-L-lysine) hexamethylenediamide (GSB-106) based on the structure of beta-turn loop 4 (BDNF-Asp
93
-Ser
94
-Lys
95
-Lys
96
-) was synthesized. GSB-106 showed neuroprotective activity
in vitro
at concentrations 10
–6
-10
–8
M and antidepressant activity
in vivo
in rats at i.p. injected doses of 0.1-1 mg/kg. The target peptide GSB-106 was obtained using three schemes in order to select the optimum synthetic pathway. The first scheme was based on the strategy of Boc/Z protecting groups using the method of pentafluorophenyl esters. The second scheme also used the Boc/Z strategy and the
N
-hydroxysuccinimide ester method. The third scheme used the Z/Boc strategy and the azide method. These three methods for synthesizing GSB-106 were compared with respect to yield and optical purity. The optimum result was obtained by using the third scheme that involved Z/Boc protecting groups and the azide method of peptide bond formation.</description><subject>Amino acids</subject><subject>Antidepressants</subject><subject>Esters</subject><subject>Medicine</subject><subject>Organic Chemistry</subject><subject>Peptides</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><issn>0091-150X</issn><issn>1573-9031</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kE9LAzEQxYMoWKsfwNuCV1NnNpv9c2yrrULRQyt4C2mSrSndzZJsD_32ptaLIDKHx8y838A8Qm4RRghQPAREqDIKyCiUZUnZGRkgLxitgOE5GQBUSJHDxyW5CmELECmWDshqeWj7TxNsSFydTB5fZ7SxjemtSnRU_62d6XqrTTJfTihCfp_IpHO9aXsrd0lr9t51Pvaqdz7Rfr-5Jhe13AVz86ND8j57Wk2f6eJt_jIdL6hinPeUZ7muUkS2To1ma14oyACrVEGZcal1BgZLVKVReVVBwdkaZA28yHJT6rhiQ3J3uruROyNsW7veS9XYoMSYsbzMsjTNo2v0hyuWNo1VrjW1jfNfAJ4A5V0I3tSi87aR_iAQxDFtcUpbxLTFMW3BIpOemBC97cZ4sXV738bv_4G-AGFMf2c</recordid><startdate>20130401</startdate><enddate>20130401</enddate><creator>Tarasyuk, A. V.</creator><creator>Pomogaibo, S. V.</creator><creator>Kurilov, D. V.</creator><creator>Gudasheva, T. A.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130401</creationdate><title>Synthesis of BDNF-mimetic dimeric dipeptide GSB-106, a potential neuroprotector drug</title><author>Tarasyuk, A. V. ; Pomogaibo, S. V. ; Kurilov, D. V. ; Gudasheva, T. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-546d92113b2ed3b57c040192c0845add40e181c8ec6990753b0af05746e8de183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Amino acids</topic><topic>Antidepressants</topic><topic>Esters</topic><topic>Medicine</topic><topic>Organic Chemistry</topic><topic>Peptides</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tarasyuk, A. V.</creatorcontrib><creatorcontrib>Pomogaibo, S. V.</creatorcontrib><creatorcontrib>Kurilov, D. V.</creatorcontrib><creatorcontrib>Gudasheva, T. A.</creatorcontrib><collection>CrossRef</collection><jtitle>Pharmaceutical chemistry journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tarasyuk, A. V.</au><au>Pomogaibo, S. V.</au><au>Kurilov, D. V.</au><au>Gudasheva, T. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of BDNF-mimetic dimeric dipeptide GSB-106, a potential neuroprotector drug</atitle><jtitle>Pharmaceutical chemistry journal</jtitle><stitle>Pharm Chem J</stitle><date>2013-04-01</date><risdate>2013</risdate><volume>47</volume><issue>1</issue><spage>20</spage><epage>27</epage><pages>20-27</pages><issn>0091-150X</issn><eissn>1573-9031</eissn><abstract>The BDNF-mimetic dimeric dipeptide
bis
-(
N
-monosuccinyl-L-seryl-L-lysine) hexamethylenediamide (GSB-106) based on the structure of beta-turn loop 4 (BDNF-Asp
93
-Ser
94
-Lys
95
-Lys
96
-) was synthesized. GSB-106 showed neuroprotective activity
in vitro
at concentrations 10
–6
-10
–8
M and antidepressant activity
in vivo
in rats at i.p. injected doses of 0.1-1 mg/kg. The target peptide GSB-106 was obtained using three schemes in order to select the optimum synthetic pathway. The first scheme was based on the strategy of Boc/Z protecting groups using the method of pentafluorophenyl esters. The second scheme also used the Boc/Z strategy and the
N
-hydroxysuccinimide ester method. The third scheme used the Z/Boc strategy and the azide method. These three methods for synthesizing GSB-106 were compared with respect to yield and optical purity. The optimum result was obtained by using the third scheme that involved Z/Boc protecting groups and the azide method of peptide bond formation.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s11094-013-0888-3</doi><tpages>8</tpages></addata></record> |
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| ispartof | Pharmaceutical chemistry journal, 2013-04, Vol.47 (1), p.20-27 |
| issn | 0091-150X 1573-9031 |
| language | eng |
| recordid | cdi_gale_infotracmisc_A336844226 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | Amino acids Antidepressants Esters Medicine Organic Chemistry Peptides Pharmacology/Toxicology Pharmacy |
| title | Synthesis of BDNF-mimetic dimeric dipeptide GSB-106, a potential neuroprotector drug |
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