Synthesis and receptor binding of oxytocin analogs containing conformationally restricted amino acids

@article{Bakos2004SynthesisAR,
  title={Synthesis and receptor binding of oxytocin analogs containing conformationally restricted amino acids},
  author={Krisztina Bakos and Judit Havass and Ferenc F{\"u}l{\"o}p and Lajos Gera and John M Stewart and George Falkay and G{\'a}bor K. T{\'o}th},
  journal={Letters in Peptide Science},
  year={2004},
  volume={8},
  pages={35-40}
}
We report the solid-phase synthesis and receptor-binding properties of eleven oxytocin analogs (Mpa-Xxx-Ile-Gln-Asn-Cys-Sar-Arg-Gly-NH2) containing non-coded amino acids in position 2: D-α- and L-α-(2-indanyl)glycine, R,S-6-methoxy-2-aminotetralin-2-carboxylic acid, D- and L-pentafluorophenylalanine, D,L-2,4-dimethylphenylalanine, D,L-2,4,6-trimethylphenylalanine, R,R- and S,S-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acid and R- and S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid… 
3 Citations
Forcefield_NCAA: Ab Initio Charge Parameters to Aid in the Discovery and Design of Therapeutic Proteins and Peptides with Unnatural Amino Acids and Their Application to Complement Inhibitors of the Compstatin Family
We describe the development and testing of ab initio derived, AMBER ff03 compatible charge parameters for a large library of 147 noncanonical amino acids including β- and N-methylated amino acids for
Synthesis of functionalised phenylalanines using rhodium catalysis in water
The efficient synthesis of substituted phenylalanine-type amino acids using a rhodium-catalysed, conjugate addition of arylboronic acids is described. The reactions are run in water and use a low

References

SHOWING 1-10 OF 29 REFERENCES
Synthesis of oxytocin antagonists containing conformationally constrained amino acids in position 2.
Design and synthesis of potent in vivo antagonists of oxytocin.
TLDR
Compounds 3 and 5 are the two most potent in vivo antagonists of oxytocin reported to date and have very low antidiuretic activities.
Design and synthesis of highly selective in vitro and in vivo uterine receptor antagonists of oxytocin: comparisons with Atosiban.
TLDR
The solid phase synthesis and some pharmacological properties of seven position two analogues of one of the authors' lead oxytocin antagonists, des-9-glycinamide, appear to be as or more potent and much more selective than the closely related OT antagonist 1-deamino.
[1-Deaminopenicillamine,4-threonine]oxytocin, a potent inhibitor of oxytocin.
TLDR
The substitution of threonine for glutamine in the antagonist [1-deaminopenicilliamine]oxytocin has effected a twofold increase in inhibitory potency, one of the most potent inhibitors of oxytocin known to date.
Synthesis and some pharmacological properties of oxytocin and vasopressin analogues with sarcosine or N-methyl-L-alanine in position 7.
TLDR
Eight analogues of oxytocin and arginine-vasopressin were synthesized, in which the proline residue in position 7 was replaced by either sarcosine or N-methylalanine, finding all of the analogues to be potent in either antidiuretic or uterine activity and also selective in action.
Deltorphin II analogues with 6-hydroxy-2-aminotetralin-2-carboxylic acid in position 1.
TLDR
Two approaches to the design of very active and highly selective delta opioid peptides were used to obtain new deltorphin analogues with altered hydrophobic and stereoelectronic properties, demonstrating a high selectivity toward delta receptors.
Potent and selective antagonists of the antidiuretic responses to arginine-vasopressin based on modifications of [1-(beta-mercapto-beta,beta-pentamethylenepropionic acid),2-D-isoleucine,4- valine]arginine-vasopressin at position 4.
TLDR
13 new analogues of the antidiuretic antagonist are synthesized in which the valine residue at position 4 has been replaced by the L-amino acids Abu, Ile, Thr, Ala, Ser, Nva, Gln, Leu, Lys, Cha, Asn, Orn, and Phe.
An exploration of the effects of L‐ and D‐tetrahydroisoquinoline‐3‐carboxylic acid substitutions at positions 2,3 and 7 in cyclic and linear antagonists of vasopressin and oxytocin and at position 3 in arginine vasopressin
  • M. Manning, L. Cheng, W. Y. Chan
  • Biology, Chemistry
    Journal of peptide science : an official publication of the European Peptide Society
  • 1995
TLDR
L‐ and D‐Tic2 substitutions led to drastic losses of anti‐V2/anti‐V1a and anti‐oxytocic potencies in peptides 2, 4, 8 and 11 and the solid‐phase synthesis of peptide 10 together with the following Tic‐substituted peptides is reported.
Properties of [3H]1-desamino-8-D-arginine vasopressin as a radioligand for vasopressin V2-receptors in rat kidney.
TLDR
In vitro autoradiography of [3H]DDAVP binding to rat kidney sections showed a very dense localization of displaceable binding over inner and outer medulla, with a much lower density in cortex, consistent with the known major localization of V2-receptors on renal collecting tubules.
In vitro degradation of some arginine-vasopressin analogs by homogenates of rat kidney, liver and serum.
TLDR
The most surprising result observed during the incubation of AVP and its analogs with rat serum was the relatively high enzymatic stability of the parent hormone compared with the modified analogs.
...
...