Solid-Phase synthesis of carboxyl-terminal N -substituted derivatives of oxytocin

1968 ◽  
Vol 87 (10) ◽  
pp. 1196-1200 ◽  
Author(s):  
H. C. Beyerman ◽  
H. Maassen van den Brink-Zimmermannová
Tetrahedron ◽  
1995 ◽  
Vol 51 (4) ◽  
pp. 1093-1106 ◽  
Author(s):  
Dewey G. McCafferty ◽  
Barney M. Bishop ◽  
Craig G. Wall ◽  
Solon G. Hughes ◽  
Sandra L. Mecklenberg ◽  
...  

1988 ◽  
Vol 53 (11) ◽  
pp. 2617-2626 ◽  
Author(s):  
Krzysztof Bankowski ◽  
Bernard Lammek ◽  
Marian Kruszynski ◽  
Maurice Manning ◽  
Janny Seto ◽  
...  

The solid phase synthesis of seven 2-O-methyl- and 2-O-ethyl-tyrosine substituted analogs of [8-arginine]vasopressin (AVP) with enhanced antidiuretic agonistic specificity is reported. These peptides are: [2-O-ethyltyrosine, 8-arginine]vasopressin (I), [2-O-methyltyrosine, 8-D-arginine]vasopressin (II), [2-O-ethyltyrosine, 8-D-arginine]vasopressin (III), [2-O-methyltyrosine, 4-valine, 8-arginine]vasopressin (IV), [2-O-ethyltyrosine, 4-valine, 8-arginine]vasopressin (V), [2-O-methyltyrosine, 4-valine, 8-D-arginine]vasopressin (VI), [2-O-ethyltyrosine, 4-valine, 8-D-arginine]vasopressin (VII). All analogs were tested for antidiuretic, antivasopressor and antioxytocic activities. Although all these new analogs are antidiuretic agonists they are antagonists of vasopressor responses to AVP, and of responses by the rat uterus to oxytocin. Thus, all seven new Tyr(Me) and Tyr(Et) containing analogs exhibit high antidiuretic specificity and have infinite antidiuretic/pressor (A/P) and antidiuretic/oxytocic (A/O) activity ratios. Some of these analogs e.g. Tyr(Me)DAVP, Tyr(Me)VAVP and Tyr(Me)VDAVP, which possess high antidiuretic activity with no pressor or oxytocic agonism, could be useful new pharmacological tools for characterizing receptors mediating specific responses to the neurohypophyseal hormones. They could also be potentially useful in the treatment of diabetes insipidus.


Author(s):  
Yoshiro Tatsu ◽  
Yasushi Shigeri ◽  
Shinji Sogabe ◽  
Noboru Yumoto ◽  
Susumu Yoshikawa

2001 ◽  
pp. 257-258
Author(s):  
Markéta Rinnová ◽  
Agnès Vidal ◽  
Adel Nefzi ◽  
Richard A. Houghten

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