New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers
Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromi...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Mollica, Adriano [verfasserIn] Pinnen, Francesco [verfasserIn] Feliciani, Federica [verfasserIn] Stefanucci, Azzurra [verfasserIn] Lucente, Gino [verfasserIn] Davis, Peg [verfasserIn] Porreca, Frank [verfasserIn] Ma, Shou-Wu [verfasserIn] Lai, Josephine [verfasserIn] Hruby, Victor J. [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2010 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: Amino acids - Wien [u.a.] : Springer, 1991, 40(2010), 5 vom: 06. Okt., Seite 1503-1511 |
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| Übergeordnetes Werk: |
volume:40 ; year:2010 ; number:5 ; day:06 ; month:10 ; pages:1503-1511 |
| Links: |
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| DOI / URN: |
10.1007/s00726-010-0760-7 |
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| Katalog-ID: |
SPR007625715 |
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| 100 | 1 | |a Mollica, Adriano |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers |
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| 520 | |a Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. | ||
| 650 | 4 | |a Activity |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Biphalin |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Dimeric peptide ligands |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Opioid peptides |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Synthesis |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Pinnen, Francesco |e verfasserin |4 aut | |
| 700 | 1 | |a Feliciani, Federica |e verfasserin |4 aut | |
| 700 | 1 | |a Stefanucci, Azzurra |e verfasserin |4 aut | |
| 700 | 1 | |a Lucente, Gino |e verfasserin |4 aut | |
| 700 | 1 | |a Davis, Peg |e verfasserin |4 aut | |
| 700 | 1 | |a Porreca, Frank |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Shou-Wu |e verfasserin |4 aut | |
| 700 | 1 | |a Lai, Josephine |e verfasserin |4 aut | |
| 700 | 1 | |a Hruby, Victor J. |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Amino acids |d Wien [u.a.] : Springer, 1991 |g 40(2010), 5 vom: 06. Okt., Seite 1503-1511 |w (DE-627)271596570 |w (DE-600)1480643-5 |x 1438-2199 |7 nnns |
| 773 | 1 | 8 | |g volume:40 |g year:2010 |g number:5 |g day:06 |g month:10 |g pages:1503-1511 |
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10.1007/s00726-010-0760-7 doi (DE-627)SPR007625715 (SPR)s00726-010-0760-7-e DE-627 ger DE-627 rakwb eng 540 ASE 35.76 bkl Mollica, Adriano verfasserin aut New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. Activity (dpeaa)DE-He213 Biphalin (dpeaa)DE-He213 Dimeric peptide ligands (dpeaa)DE-He213 Opioid peptides (dpeaa)DE-He213 Synthesis (dpeaa)DE-He213 Pinnen, Francesco verfasserin aut Feliciani, Federica verfasserin aut Stefanucci, Azzurra verfasserin aut Lucente, Gino verfasserin aut Davis, Peg verfasserin aut Porreca, Frank verfasserin aut Ma, Shou-Wu verfasserin aut Lai, Josephine verfasserin aut Hruby, Victor J. verfasserin aut Enthalten in Amino acids Wien [u.a.] : Springer, 1991 40(2010), 5 vom: 06. Okt., Seite 1503-1511 (DE-627)271596570 (DE-600)1480643-5 1438-2199 nnns volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 https://dx.doi.org/10.1007/s00726-010-0760-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.76 ASE AR 40 2010 5 06 10 1503-1511 |
| spelling |
10.1007/s00726-010-0760-7 doi (DE-627)SPR007625715 (SPR)s00726-010-0760-7-e DE-627 ger DE-627 rakwb eng 540 ASE 35.76 bkl Mollica, Adriano verfasserin aut New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. Activity (dpeaa)DE-He213 Biphalin (dpeaa)DE-He213 Dimeric peptide ligands (dpeaa)DE-He213 Opioid peptides (dpeaa)DE-He213 Synthesis (dpeaa)DE-He213 Pinnen, Francesco verfasserin aut Feliciani, Federica verfasserin aut Stefanucci, Azzurra verfasserin aut Lucente, Gino verfasserin aut Davis, Peg verfasserin aut Porreca, Frank verfasserin aut Ma, Shou-Wu verfasserin aut Lai, Josephine verfasserin aut Hruby, Victor J. verfasserin aut Enthalten in Amino acids Wien [u.a.] : Springer, 1991 40(2010), 5 vom: 06. Okt., Seite 1503-1511 (DE-627)271596570 (DE-600)1480643-5 1438-2199 nnns volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 https://dx.doi.org/10.1007/s00726-010-0760-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.76 ASE AR 40 2010 5 06 10 1503-1511 |
| allfields_unstemmed |
10.1007/s00726-010-0760-7 doi (DE-627)SPR007625715 (SPR)s00726-010-0760-7-e DE-627 ger DE-627 rakwb eng 540 ASE 35.76 bkl Mollica, Adriano verfasserin aut New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. Activity (dpeaa)DE-He213 Biphalin (dpeaa)DE-He213 Dimeric peptide ligands (dpeaa)DE-He213 Opioid peptides (dpeaa)DE-He213 Synthesis (dpeaa)DE-He213 Pinnen, Francesco verfasserin aut Feliciani, Federica verfasserin aut Stefanucci, Azzurra verfasserin aut Lucente, Gino verfasserin aut Davis, Peg verfasserin aut Porreca, Frank verfasserin aut Ma, Shou-Wu verfasserin aut Lai, Josephine verfasserin aut Hruby, Victor J. verfasserin aut Enthalten in Amino acids Wien [u.a.] : Springer, 1991 40(2010), 5 vom: 06. Okt., Seite 1503-1511 (DE-627)271596570 (DE-600)1480643-5 1438-2199 nnns volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 https://dx.doi.org/10.1007/s00726-010-0760-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.76 ASE AR 40 2010 5 06 10 1503-1511 |
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10.1007/s00726-010-0760-7 doi (DE-627)SPR007625715 (SPR)s00726-010-0760-7-e DE-627 ger DE-627 rakwb eng 540 ASE 35.76 bkl Mollica, Adriano verfasserin aut New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. Activity (dpeaa)DE-He213 Biphalin (dpeaa)DE-He213 Dimeric peptide ligands (dpeaa)DE-He213 Opioid peptides (dpeaa)DE-He213 Synthesis (dpeaa)DE-He213 Pinnen, Francesco verfasserin aut Feliciani, Federica verfasserin aut Stefanucci, Azzurra verfasserin aut Lucente, Gino verfasserin aut Davis, Peg verfasserin aut Porreca, Frank verfasserin aut Ma, Shou-Wu verfasserin aut Lai, Josephine verfasserin aut Hruby, Victor J. verfasserin aut Enthalten in Amino acids Wien [u.a.] : Springer, 1991 40(2010), 5 vom: 06. Okt., Seite 1503-1511 (DE-627)271596570 (DE-600)1480643-5 1438-2199 nnns volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 https://dx.doi.org/10.1007/s00726-010-0760-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.76 ASE AR 40 2010 5 06 10 1503-1511 |
| allfieldsSound |
10.1007/s00726-010-0760-7 doi (DE-627)SPR007625715 (SPR)s00726-010-0760-7-e DE-627 ger DE-627 rakwb eng 540 ASE 35.76 bkl Mollica, Adriano verfasserin aut New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers 2010 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. Activity (dpeaa)DE-He213 Biphalin (dpeaa)DE-He213 Dimeric peptide ligands (dpeaa)DE-He213 Opioid peptides (dpeaa)DE-He213 Synthesis (dpeaa)DE-He213 Pinnen, Francesco verfasserin aut Feliciani, Federica verfasserin aut Stefanucci, Azzurra verfasserin aut Lucente, Gino verfasserin aut Davis, Peg verfasserin aut Porreca, Frank verfasserin aut Ma, Shou-Wu verfasserin aut Lai, Josephine verfasserin aut Hruby, Victor J. verfasserin aut Enthalten in Amino acids Wien [u.a.] : Springer, 1991 40(2010), 5 vom: 06. Okt., Seite 1503-1511 (DE-627)271596570 (DE-600)1480643-5 1438-2199 nnns volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 https://dx.doi.org/10.1007/s00726-010-0760-7 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_267 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 35.76 ASE AR 40 2010 5 06 10 1503-1511 |
| language |
English |
| source |
Enthalten in Amino acids 40(2010), 5 vom: 06. Okt., Seite 1503-1511 volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 |
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Enthalten in Amino acids 40(2010), 5 vom: 06. Okt., Seite 1503-1511 volume:40 year:2010 number:5 day:06 month:10 pages:1503-1511 |
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findex.gbv.de |
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Activity Biphalin Dimeric peptide ligands Opioid peptides Synthesis |
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Amino acids |
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Mollica, Adriano @@aut@@ Pinnen, Francesco @@aut@@ Feliciani, Federica @@aut@@ Stefanucci, Azzurra @@aut@@ Lucente, Gino @@aut@@ Davis, Peg @@aut@@ Porreca, Frank @@aut@@ Ma, Shou-Wu @@aut@@ Lai, Josephine @@aut@@ Hruby, Victor J. @@aut@@ |
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2010-10-06T00:00:00Z |
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SPR007625715 |
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The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. 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Mollica, Adriano |
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Mollica, Adriano ddc 540 bkl 35.76 misc Activity misc Biphalin misc Dimeric peptide ligands misc Opioid peptides misc Synthesis New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers |
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540 ASE 35.76 bkl New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers Activity (dpeaa)DE-He213 Biphalin (dpeaa)DE-He213 Dimeric peptide ligands (dpeaa)DE-He213 Opioid peptides (dpeaa)DE-He213 Synthesis (dpeaa)DE-He213 |
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New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers |
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Mollica, Adriano Pinnen, Francesco Feliciani, Federica Stefanucci, Azzurra Lucente, Gino Davis, Peg Porreca, Frank Ma, Shou-Wu Lai, Josephine Hruby, Victor J. |
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Mollica, Adriano |
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new potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers |
| title_auth |
New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers |
| abstract |
Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. |
| abstractGer |
Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. |
| abstract_unstemmed |
Abstract We report the synthesis and the biological evaluation of two new analogues of the potent dimeric opioid peptide biphalin. The performed modification is based on the replacement of two key structural elements of the native biphalin, namely: the hydrazine bridge which joins the two palindromic moieties and the phenylalanine residues at the 4,4′ positions of the backbone. The new analogues 9 and 10 contain 1,2-phenylenediamine and piperazine, respectively, in place of the hydrazidic linker and p-fluoro-l-phenylalanine residues at 4 and 4′ positions. Binding values are: %$ K_{\text{i}}^{\mu } = 0.51\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 12.8\,{\text{nM}} %$ for compound 9, %$ K_{\text{i}}^{\mu } = 0.09\,{\text{nM}} %$ and %$ K_{\text{i}}^{\delta } = 0.11\,{\text{nM}} %$ for analogue 10. |
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New potent biphalin analogues containing p-fluoro-l-phenylalanine at the 4,4′ positions and non-hydrazine linkers |
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Pinnen, Francesco Feliciani, Federica Stefanucci, Azzurra Lucente, Gino Davis, Peg Porreca, Frank Ma, Shou-Wu Lai, Josephine Hruby, Victor J. |
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Pinnen, Francesco Feliciani, Federica Stefanucci, Azzurra Lucente, Gino Davis, Peg Porreca, Frank Ma, Shou-Wu Lai, Josephine Hruby, Victor J. |
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| score |
7.4017696 |