Wyniki wyszukiwania

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

100%

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

Acta Biochimica Polonica

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2007

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tom 54

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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

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The pineal and oxytocin synthesis

84%

Bojanowska E., Juszczak M., Guzek J. W., Dabrowski R.

Journal of Physiology and Pharmacology

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1999

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tom 50

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nr 1

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Glucagon-like peptide-1 [7-36] amide and the release of neurohypophysial hormones: in vivo and in vitro studies

84%

Bojanowska E., Stempniak B., Juszczak M.

Journal of Physiology and Pharmacology. Supplement

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2001

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tom 52

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nr 2

4

Thyrotropin-releasing hormone affects the oxytocin, vasopressin and prolactin release in female rats during midlactation: relation to suckling

67%

Ciosek J., Guzek J. W.

Journal of Physiology and Pharmacology

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1998

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tom 49

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nr 1

5

The influence of vasopressin or oxytocin on thyroid-stimulating hormone and thyroid hormones' concentrations in blood plasma of euthyroid rats

67%

Ciosek J., Stempniak B.

Journal of Physiology and Pharmacology

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1997

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tom 48

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nr 4

6

Control of neurohypophysial hormone secretion, blood osmolality and volume in pregnancy

59%

Brunton P. J., Arunachalam S., Russell J. A.

Journal of Physiology and Pharmacology. Supplement

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2008

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tom 59

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nr 8

Ograniczanie wyników

3 Journal of Physiology and Pharmacology

2 Journal of Physiology and Pharmacology. Supplement

1 Acta Biochimica Polonica

2 Bojanowska E.

2 Ciosek J.

2 Guzek J. W.

2 Juszczak M.

2 Stempniak B.

1 Arunachalam S.

1 Borovickova L.

1 Brunton P. J.

1 Dabrowski R.

1 Grzonka Z.

1 Manturewicz M.

1 Russell J. A.

1 Slaninova J.

1 2008

1 2007

1 2001

1 1999

1 1998

1 1997

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

The pineal and oxytocin synthesis

Glucagon-like peptide-1 [7-36] amide and the release of neurohypophysial hormones: in vivo and in vitro studies

Thyrotropin-releasing hormone affects the oxytocin, vasopressin and prolactin release in female rats during midlactation: relation to suckling

The influence of vasopressin or oxytocin on thyroid-stimulating hormone and thyroid hormones' concentrations in blood plasma of euthyroid rats

Control of neurohypophysial hormone secretion, blood osmolality and volume in pregnancy