Endomorphin-2 with a beta turn backbone constraint retains the potent mu-opioid receptor agonist properties: IF 4.898

Csaba Tömböly; Steven Ballet; Debby Feytens; Katalin E. Köver; Borics Attila; Sandor Lovas; Mahmoud Al-Khrasani; Furst Zsuzsanna; Géza Tóth; Sandor Benyhe; Dirk Tourwe

Endomorphin-2 with a beta turn backbone constraint retains the potent mu-opioid receptor agonist properties: IF 4.898

Csaba Tömböly, Steven Ballet, Debby Feytens, Katalin E. Köver, Borics Attila, Sandor Lovas, Mahmoud Al-Khrasani, Furst Zsuzsanna, Géza Tóth, Sandor Benyhe, Dirk Tourwe

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 and Tyr-(R/S)-Aba-Gly-Phe-NH2. The (R)-spiro analog was found to be a potent and selective ?-opioid agonist/partial agonist (Kiµ = 29.3 nM, IC50 = 50 nM, Ke = 0.57). NMR expts. and mol. modeling indicated that its backbone adopts mainly a ?-turn in aq. soln.

Original language	English
Pages (from-to)	173-177
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	51
Issue number	1
Publication status	Published - 2008

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title = "Endomorphin-2 with a beta turn backbone constraint retains the potent mu-opioid receptor agonist properties: IF 4.898",

abstract = "The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 and Tyr-(R/S)-Aba-Gly-Phe-NH2. The (R)-spiro analog was found to be a potent and selective ?-opioid agonist/partial agonist (Kiµ = 29.3 nM, IC50 = 50 nM, Ke = 0.57). NMR expts. and mol. modeling indicated that its backbone adopts mainly a ?-turn in aq. soln.",

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year = "2008",

language = "English",

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journal = "Journal of Medicinal Chemistry",

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T1 - Endomorphin-2 with a beta turn backbone constraint retains the potent mu-opioid receptor agonist properties

T2 - IF 4.898

AU - Tömböly, Csaba

AU - Ballet, Steven

AU - Feytens, Debby

AU - Köver, Katalin E.

AU - Attila, Borics

AU - Lovas, Sandor

AU - Al-Khrasani, Mahmoud

AU - Zsuzsanna, Furst

AU - Tóth, Géza

AU - Benyhe, Sandor

AU - Tourwe, Dirk

PY - 2008

Y1 - 2008

N2 - The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 and Tyr-(R/S)-Aba-Gly-Phe-NH2. The (R)-spiro analog was found to be a potent and selective ?-opioid agonist/partial agonist (Kiµ = 29.3 nM, IC50 = 50 nM, Ke = 0.57). NMR expts. and mol. modeling indicated that its backbone adopts mainly a ?-turn in aq. soln.

AB - The constitutional similarity with different secondary structure preference between the Aba-Gly and the spiro-Aba-Gly scaffolds were exploited to design the novel endomorphin-2 analogs Tyr-spiro-(R/S)-Aba-Gly-Phe-NH2 and Tyr-(R/S)-Aba-Gly-Phe-NH2. The (R)-spiro analog was found to be a potent and selective ?-opioid agonist/partial agonist (Kiµ = 29.3 nM, IC50 = 50 nM, Ke = 0.57). NMR expts. and mol. modeling indicated that its backbone adopts mainly a ?-turn in aq. soln.

KW - peptides

M3 - Article

SN - 0022-2623

VL - 51

SP - 173

EP - 177

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 1

ER -

Endomorphin-2 with a beta turn backbone constraint retains the potent mu-opioid receptor agonist properties: IF 4.898

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