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Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor
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| Zeitschriftentitel: | Biopolymers |
|---|---|
| Personen und Körperschaften: | , , , , , , , , |
| In: | Biopolymers, 33, 1993, 6, S. 915-926 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Tallon, M. Ron, D. Halle, D. Amodeo, P. Saviano, G. Temussi, P. A. Selinger, Z. Naider, F. Chorev, M. Tallon, M. Ron, D. Halle, D. Amodeo, P. Saviano, G. Temussi, P. A. Selinger, Z. Naider, F. Chorev, M. |
|---|---|
| author |
Tallon, M. Ron, D. Halle, D. Amodeo, P. Saviano, G. Temussi, P. A. Selinger, Z. Naider, F. Chorev, M. |
| spellingShingle |
Tallon, M. Ron, D. Halle, D. Amodeo, P. Saviano, G. Temussi, P. A. Selinger, Z. Naider, F. Chorev, M. Biopolymers Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor Organic Chemistry Biomaterials Biochemistry General Medicine Biophysics |
| author_sort |
tallon, m. |
| spelling |
Tallon, M. Ron, D. Halle, D. Amodeo, P. Saviano, G. Temussi, P. A. Selinger, Z. Naider, F. Chorev, M. 0006-3525 1097-0282 Wiley Organic Chemistry Biomaterials Biochemistry General Medicine Biophysics http://dx.doi.org/10.1002/bip.360330607 <jats:title>Abstract</jats:title><jats:p>A highly potent and selective agonist to the tachykinin NK‐3 receptor, [pGlu<jats:sup>6</jats:sup>, N‐MePhe<jats:sup>8</jats:sup>, Aib<jats:sup>9</jats:sup>] substance P (6–11) (<jats:bold>I</jats:bold>), was synthesized via the solid phase method. The ED<jats:sub>50</jats:sub> of <jats:bold>I</jats:bold> was 4n <jats:italic>M</jats:italic> in the guinea pig ileum in the absence of atropine (NK‐1 + NK‐3 receptors) and this agonist was 5000‐fold less potent in the presence of atropine (NK‐1 receptor). The analogue was virtually inactive in the rat vas deferens (NK‐2 receptor). A detailed analysis of the solution conformation of this analogue in DMSO‐d<jats:sub>6</jats:sub> and in a DMSO‐d<jats:sub>6</jats:sub> H<jats:sub>2</jats:sub>O cryornixture was carried out by a combination of <jats:sup>1</jats:sup>H‐nmr 2D techniques (DQF‐COSY, TOCSY, NOESY and ROESY) and model building based on empirical energy calculations. Peptide <jats:bold>I</jats:bold> exists as a mixture of isomers containing <jats:italic>cis</jats:italic> and <jats:italic>trans</jats:italic> Phe‐N‐MePhe peptide bonds. The main isomer, containing a <jats:italic>cis</jats:italic> Phe‐N‐MePhe peptide bond, shows a preferred folded conformation characterized by a type VI β‐turn with Phe and N‐MePhe in the <jats:italic>i</jats:italic> + 1 and <jats:italic>i</jats:italic> + 2 positions. The turn is followed by a helical segment extending to the C‐terminal. This conformation is compared to previously reported conformations of other selective tachykinin agonists and may be a promising lead for the design of novel NK‐3 agonists with additional conformational constraints. © 1993 John Wiley & Sons, Inc.</jats:p> Synthesis, biological activity, and conformational analysis of [pGlu<sup>6</sup>, N‐MePhe<sup>8</sup>, Aib<sup>9</sup>] substance P (6–11): A selective agonist for the NK‐3 receptor Biopolymers |
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10.1002/bip.360330607 |
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Online |
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Chemie und Pharmazie Biologie Technik Physik |
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Wiley, 1993 |
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1993 |
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| title |
Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_unstemmed |
Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_full |
Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_fullStr |
Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_full_unstemmed |
Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_short |
Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_sort |
synthesis, biological activity, and conformational analysis of [pglu<sup>6</sup>, n‐mephe<sup>8</sup>, aib<sup>9</sup>] substance p (6–11): a selective agonist for the nk‐3 receptor |
| topic |
Organic Chemistry Biomaterials Biochemistry General Medicine Biophysics |
| url |
http://dx.doi.org/10.1002/bip.360330607 |
| publishDate |
1993 |
| physical |
915-926 |
| description |
<jats:title>Abstract</jats:title><jats:p>A highly potent and selective agonist to the tachykinin NK‐3 receptor, [pGlu<jats:sup>6</jats:sup>, N‐MePhe<jats:sup>8</jats:sup>, Aib<jats:sup>9</jats:sup>] substance P (6–11) (<jats:bold>I</jats:bold>), was synthesized via the solid phase method. The ED<jats:sub>50</jats:sub> of <jats:bold>I</jats:bold> was 4n <jats:italic>M</jats:italic> in the guinea pig ileum in the absence of atropine (NK‐1 + NK‐3 receptors) and this agonist was 5000‐fold less potent in the presence of atropine (NK‐1 receptor). The analogue was virtually inactive in the rat vas deferens (NK‐2 receptor). A detailed analysis of the solution conformation of this analogue in DMSO‐d<jats:sub>6</jats:sub> and in a DMSO‐d<jats:sub>6</jats:sub> H<jats:sub>2</jats:sub>O cryornixture was carried out by a combination of <jats:sup>1</jats:sup>H‐nmr 2D techniques (DQF‐COSY, TOCSY, NOESY and ROESY) and model building based on empirical energy calculations. Peptide <jats:bold>I</jats:bold> exists as a mixture of isomers containing <jats:italic>cis</jats:italic> and <jats:italic>trans</jats:italic> Phe‐N‐MePhe peptide bonds. The main isomer, containing a <jats:italic>cis</jats:italic> Phe‐N‐MePhe peptide bond, shows a preferred folded conformation characterized by a type VI β‐turn with Phe and N‐MePhe in the <jats:italic>i</jats:italic> + 1 and <jats:italic>i</jats:italic> + 2 positions. The turn is followed by a helical segment extending to the C‐terminal. This conformation is compared to previously reported conformations of other selective tachykinin agonists and may be a promising lead for the design of novel NK‐3 agonists with additional conformational constraints. © 1993 John Wiley & Sons, Inc.</jats:p> |
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| author | Tallon, M., Ron, D., Halle, D., Amodeo, P., Saviano, G., Temussi, P. A., Selinger, Z., Naider, F., Chorev, M. |
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| description | <jats:title>Abstract</jats:title><jats:p>A highly potent and selective agonist to the tachykinin NK‐3 receptor, [pGlu<jats:sup>6</jats:sup>, N‐MePhe<jats:sup>8</jats:sup>, Aib<jats:sup>9</jats:sup>] substance P (6–11) (<jats:bold>I</jats:bold>), was synthesized via the solid phase method. The ED<jats:sub>50</jats:sub> of <jats:bold>I</jats:bold> was 4n <jats:italic>M</jats:italic> in the guinea pig ileum in the absence of atropine (NK‐1 + NK‐3 receptors) and this agonist was 5000‐fold less potent in the presence of atropine (NK‐1 receptor). The analogue was virtually inactive in the rat vas deferens (NK‐2 receptor). A detailed analysis of the solution conformation of this analogue in DMSO‐d<jats:sub>6</jats:sub> and in a DMSO‐d<jats:sub>6</jats:sub> H<jats:sub>2</jats:sub>O cryornixture was carried out by a combination of <jats:sup>1</jats:sup>H‐nmr 2D techniques (DQF‐COSY, TOCSY, NOESY and ROESY) and model building based on empirical energy calculations. Peptide <jats:bold>I</jats:bold> exists as a mixture of isomers containing <jats:italic>cis</jats:italic> and <jats:italic>trans</jats:italic> Phe‐N‐MePhe peptide bonds. The main isomer, containing a <jats:italic>cis</jats:italic> Phe‐N‐MePhe peptide bond, shows a preferred folded conformation characterized by a type VI β‐turn with Phe and N‐MePhe in the <jats:italic>i</jats:italic> + 1 and <jats:italic>i</jats:italic> + 2 positions. The turn is followed by a helical segment extending to the C‐terminal. This conformation is compared to previously reported conformations of other selective tachykinin agonists and may be a promising lead for the design of novel NK‐3 agonists with additional conformational constraints. © 1993 John Wiley & Sons, Inc.</jats:p> |
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| imprint | Wiley, 1993 |
| imprint_str_mv | Wiley, 1993 |
| institution | DE-Pl11, DE-Rs1, DE-14, DE-105, DE-Ch1, DE-L229, DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Zi4, DE-Gla1, DE-15 |
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| spelling | Tallon, M. Ron, D. Halle, D. Amodeo, P. Saviano, G. Temussi, P. A. Selinger, Z. Naider, F. Chorev, M. 0006-3525 1097-0282 Wiley Organic Chemistry Biomaterials Biochemistry General Medicine Biophysics http://dx.doi.org/10.1002/bip.360330607 <jats:title>Abstract</jats:title><jats:p>A highly potent and selective agonist to the tachykinin NK‐3 receptor, [pGlu<jats:sup>6</jats:sup>, N‐MePhe<jats:sup>8</jats:sup>, Aib<jats:sup>9</jats:sup>] substance P (6–11) (<jats:bold>I</jats:bold>), was synthesized via the solid phase method. The ED<jats:sub>50</jats:sub> of <jats:bold>I</jats:bold> was 4n <jats:italic>M</jats:italic> in the guinea pig ileum in the absence of atropine (NK‐1 + NK‐3 receptors) and this agonist was 5000‐fold less potent in the presence of atropine (NK‐1 receptor). The analogue was virtually inactive in the rat vas deferens (NK‐2 receptor). A detailed analysis of the solution conformation of this analogue in DMSO‐d<jats:sub>6</jats:sub> and in a DMSO‐d<jats:sub>6</jats:sub> H<jats:sub>2</jats:sub>O cryornixture was carried out by a combination of <jats:sup>1</jats:sup>H‐nmr 2D techniques (DQF‐COSY, TOCSY, NOESY and ROESY) and model building based on empirical energy calculations. Peptide <jats:bold>I</jats:bold> exists as a mixture of isomers containing <jats:italic>cis</jats:italic> and <jats:italic>trans</jats:italic> Phe‐N‐MePhe peptide bonds. The main isomer, containing a <jats:italic>cis</jats:italic> Phe‐N‐MePhe peptide bond, shows a preferred folded conformation characterized by a type VI β‐turn with Phe and N‐MePhe in the <jats:italic>i</jats:italic> + 1 and <jats:italic>i</jats:italic> + 2 positions. The turn is followed by a helical segment extending to the C‐terminal. This conformation is compared to previously reported conformations of other selective tachykinin agonists and may be a promising lead for the design of novel NK‐3 agonists with additional conformational constraints. © 1993 John Wiley & Sons, Inc.</jats:p> Synthesis, biological activity, and conformational analysis of [pGlu<sup>6</sup>, N‐MePhe<sup>8</sup>, Aib<sup>9</sup>] substance P (6–11): A selective agonist for the NK‐3 receptor Biopolymers |
| spellingShingle | Tallon, M., Ron, D., Halle, D., Amodeo, P., Saviano, G., Temussi, P. A., Selinger, Z., Naider, F., Chorev, M., Biopolymers, Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor, Organic Chemistry, Biomaterials, Biochemistry, General Medicine, Biophysics |
| title | Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_full | Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_fullStr | Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_full_unstemmed | Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_short | Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| title_sort | synthesis, biological activity, and conformational analysis of [pglu<sup>6</sup>, n‐mephe<sup>8</sup>, aib<sup>9</sup>] substance p (6–11): a selective agonist for the nk‐3 receptor |
| title_unstemmed | Synthesis, biological activity, and conformational analysis of [pGlu6, N‐MePhe8, Aib9] substance P (6–11): A selective agonist for the NK‐3 receptor |
| topic | Organic Chemistry, Biomaterials, Biochemistry, General Medicine, Biophysics |
| url | http://dx.doi.org/10.1002/bip.360330607 |