Antiamnesic properties of analogs and mimetics of the tripeptide human urocortin 3

G. Telegdy, Anita Kármen Kovács, Kinga Rákosi, Márta Zarándi, G. Tóth

Research output: Contribution to journalArticle

Abstract

Amnesia is a deficit in memory caused by brain damage, disease, or trauma. Until now, there are no successful medications on the drug market available to treat amnesia. Short analogs and mimetics of human urocortin 3 (Ucn 3) tripeptide were synthetized and tested for their action against amnesia induced by eletroconvulsion in mice. Among the 16 investigated derivatives of Ucn 3 tripeptide, eight compounds displayed antiamnesic effect. Our results proved that the configuration of chiral center of glutamine does not affect the antiamnesic properties. Alkyl amide or isoleucyl amide at the C-terminus may lead to antiamnesic compounds. As concerned the N-terminus, acetyl, Boc, and alkyl ureido moieties were found among the active analogs, but the free amino function at the N-terminus usually led to an inactive derivatives. These observations may lead to the design and synthesis of small peptidomimetics and amino acid derivatives as antiamnesic drug candidates, although the elucidation of the mechanism of the action requires further investigations.

Original languageEnglish
Pages (from-to)2261-2266
Number of pages6
JournalAmino Acids
Volume48
Issue number9
DOIs
Publication statusPublished - Sep 1 2016

Fingerprint

Amnesia
Derivatives
Amides
Urocortins
Peptidomimetics
Memory Disorders
Brain Diseases
Glutamine
Pharmaceutical Preparations
Brain
Data storage equipment
Amino Acids
human UCN3 protein

Keywords

  • Antiamnesic effect
  • Passive avoidance learning
  • Peptidomimetics
  • Urocortin 3 fragments

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Antiamnesic properties of analogs and mimetics of the tripeptide human urocortin 3. / Telegdy, G.; Kovács, Anita Kármen; Rákosi, Kinga; Zarándi, Márta; Tóth, G.

In: Amino Acids, Vol. 48, No. 9, 01.09.2016, p. 2261-2266.

Research output: Contribution to journalArticle

Telegdy, G. ; Kovács, Anita Kármen ; Rákosi, Kinga ; Zarándi, Márta ; Tóth, G. / Antiamnesic properties of analogs and mimetics of the tripeptide human urocortin 3. In: Amino Acids. 2016 ; Vol. 48, No. 9. pp. 2261-2266.
@article{f94283a6d31c4f75b4de19e6fe8ff985,
title = "Antiamnesic properties of analogs and mimetics of the tripeptide human urocortin 3",
abstract = "Amnesia is a deficit in memory caused by brain damage, disease, or trauma. Until now, there are no successful medications on the drug market available to treat amnesia. Short analogs and mimetics of human urocortin 3 (Ucn 3) tripeptide were synthetized and tested for their action against amnesia induced by eletroconvulsion in mice. Among the 16 investigated derivatives of Ucn 3 tripeptide, eight compounds displayed antiamnesic effect. Our results proved that the configuration of chiral center of glutamine does not affect the antiamnesic properties. Alkyl amide or isoleucyl amide at the C-terminus may lead to antiamnesic compounds. As concerned the N-terminus, acetyl, Boc, and alkyl ureido moieties were found among the active analogs, but the free amino function at the N-terminus usually led to an inactive derivatives. These observations may lead to the design and synthesis of small peptidomimetics and amino acid derivatives as antiamnesic drug candidates, although the elucidation of the mechanism of the action requires further investigations.",
keywords = "Antiamnesic effect, Passive avoidance learning, Peptidomimetics, Urocortin 3 fragments",
author = "G. Telegdy and Kov{\'a}cs, {Anita K{\'a}rmen} and Kinga R{\'a}kosi and M{\'a}rta Zar{\'a}ndi and G. T{\'o}th",
year = "2016",
month = "9",
day = "1",
doi = "10.1007/s00726-016-2268-2",
language = "English",
volume = "48",
pages = "2261--2266",
journal = "Amino Acids",
issn = "0939-4451",
publisher = "Springer Wien",
number = "9",

}

TY - JOUR

T1 - Antiamnesic properties of analogs and mimetics of the tripeptide human urocortin 3

AU - Telegdy, G.

AU - Kovács, Anita Kármen

AU - Rákosi, Kinga

AU - Zarándi, Márta

AU - Tóth, G.

PY - 2016/9/1

Y1 - 2016/9/1

N2 - Amnesia is a deficit in memory caused by brain damage, disease, or trauma. Until now, there are no successful medications on the drug market available to treat amnesia. Short analogs and mimetics of human urocortin 3 (Ucn 3) tripeptide were synthetized and tested for their action against amnesia induced by eletroconvulsion in mice. Among the 16 investigated derivatives of Ucn 3 tripeptide, eight compounds displayed antiamnesic effect. Our results proved that the configuration of chiral center of glutamine does not affect the antiamnesic properties. Alkyl amide or isoleucyl amide at the C-terminus may lead to antiamnesic compounds. As concerned the N-terminus, acetyl, Boc, and alkyl ureido moieties were found among the active analogs, but the free amino function at the N-terminus usually led to an inactive derivatives. These observations may lead to the design and synthesis of small peptidomimetics and amino acid derivatives as antiamnesic drug candidates, although the elucidation of the mechanism of the action requires further investigations.

AB - Amnesia is a deficit in memory caused by brain damage, disease, or trauma. Until now, there are no successful medications on the drug market available to treat amnesia. Short analogs and mimetics of human urocortin 3 (Ucn 3) tripeptide were synthetized and tested for their action against amnesia induced by eletroconvulsion in mice. Among the 16 investigated derivatives of Ucn 3 tripeptide, eight compounds displayed antiamnesic effect. Our results proved that the configuration of chiral center of glutamine does not affect the antiamnesic properties. Alkyl amide or isoleucyl amide at the C-terminus may lead to antiamnesic compounds. As concerned the N-terminus, acetyl, Boc, and alkyl ureido moieties were found among the active analogs, but the free amino function at the N-terminus usually led to an inactive derivatives. These observations may lead to the design and synthesis of small peptidomimetics and amino acid derivatives as antiamnesic drug candidates, although the elucidation of the mechanism of the action requires further investigations.

KW - Antiamnesic effect

KW - Passive avoidance learning

KW - Peptidomimetics

KW - Urocortin 3 fragments

UR - http://www.scopus.com/inward/record.url?scp=84983035416&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84983035416&partnerID=8YFLogxK

U2 - 10.1007/s00726-016-2268-2

DO - 10.1007/s00726-016-2268-2

M3 - Article

C2 - 27262310

AN - SCOPUS:84983035416

VL - 48

SP - 2261

EP - 2266

JO - Amino Acids

JF - Amino Acids

SN - 0939-4451

IS - 9

ER -