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Low Molecular Mass Inhibitors of Bovine beta-Trypsin Containing Binding Loop Fragment of CMTI-III. Synthesis and Evaluation of Inhibitory Activity

100%

Frąszczak P. , Lis K. , Jaśkiewicz A. , Miecznikowska H. , Rolka K. , Kupryszewski G.

tom Vol. 75, nr 12

1863-1868

Three peptides with sequences related to the binding loop of Cucurbita maxima trypsin inhibitor III were obtained: [G3,GIO]CMTI-HI (1-10) (1), [A1,G3,A9,G10]MTlII (1-10) (2) and c(K-A-A-P-R-I-L-M-K-Y-A-E) (3). All peptides were synthesized by the solid-phase methodusing the Fmoc/Bu t procedure. Peptide 1 revealed a relatively high inhibitory activity (association equilibrium constant with bovine beta-trypsin Ka = 4 x 10 9 [M -1]). Significantly lower activity (Ka = 3.6x l O4 [M -1) was obtained for peptide 3. Peptide 2 appeared to be inactive.

Oxytocin analogues with amide groups substituted by tetrazole groups in position 4, 5 or 9

60%

Manturewicz M. , Grzonka Z. , Borovickova L. , Slaninova J.

tom 54

nr 4

805-811

Eleven oxytocin analogues substituted in position 4, 5 or 9 by tetrazole analogues of amino acids were prepared using solid-phase peptide synthesis method and tested for rat uterotonic in vitro and pressor activities, as well as for their affinity to human oxytocin receptor. The tetrazolic group has been used as a bioisosteric substitution of carboxylic, ester or amide groups in structure–activity relationship studies of biologically active compounds. Replacement of the amide groups of Gln 4 and Asn 5 in oxytocin by tetrazole analogues of aspartic, glutamic and α-aminoadipic acids containing the tetrazole moiety in the side chains leads to analogues with decreased biological activities. Oxytocin analogues in which the glycine amide residue in position 9 was substituted by tetrazole analogues of glycine had diminished activities as well. The analysis of differences in rat uterotonic activity and in the affinity to human oxytocin receptors of analogues containing either an acidic 5-substituted tetrazolic group or a neutral 1,5- or 2,5-tetrazole nucleus makes it possible to draw some new conclusions concerning the role of the amide group of amino acids in positions 4, 5 and 9 of oxytocin for its activity. The data suggest that the interaction of the side chain of Gln 4 with the oxytocin receptor is influenced mainly by electronic effects and the hydrogen bonding capacity of the amide group. Steric effects of the side chain are minor. Substitution of Asn 5 by its tetrazole derivative gave an analogue of very low activity. The result suggests that in the interaction between the amide group of Asn 5 and the binding sites of oxytocic receptor hydrogen bonds are of less importance than the spatial requirements for this group