Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities

Padma Nair; Takashi Yamamoto; Tally M. Largent-Milnes; Scott Cowell; Vinod Kulkarni; Sharif Moye; Edita Navratilova; Peg Davis; Shou Wu Ma; Todd W. Vanderah; Josephine Lai; Frank Porreca; Victor J Hruby

doi:10.1016/j.bmcl.2013.06.065

Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities

Padma Nair
, Takashi Yamamoto
, Tally M. Largent-Milnes
, Scott Cowell
, Vinod Kulkarni
, Sharif Moye
, Edita Navratilova
, Peg Davis
, Shou Wu Ma
, Todd W. Vanderah
, Josephine Lai
, Frank Porreca
, Victor J Hruby

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

12 Scopus citations

Abstract

The optimization and truncation of our lead peptide-derived ligand TY005 possessing eight amino-acid residues was performed. Among the synthesized derivatives, NP30 (Tyr¹-DAla²-Gly³-Phe ⁴-Gly⁵-Trp⁶-O-[3′,5′-Bzl(CF ₃)₂]) showed balanced and potent opioid agonist as well as substance P antagonist activities in isolated tissue-based assays, together with significant antinociceptive and antiallodynic activities in vivo.

Original language	English (US)
Pages (from-to)	4975-4978
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	17
DOIs	https://doi.org/10.1016/j.bmcl.2013.06.065
State	Published - Sep 1 2013

Keywords

Bifunctional compounds
NMR structure
Neutokinin-1 receptor antagonists
Opioid receptor agonists
Truncation of peptide sequence

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2013.06.065

Cite this

Nair, P., Yamamoto, T., Largent-Milnes, T. M., Cowell, S., Kulkarni, V., Moye, S., Navratilova, E., Davis, P., Ma, S. W., Vanderah, T. W., Lai, J., Porreca, F., & Hruby, V. J. (2013). Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities. Bioorganic and Medicinal Chemistry Letters, 23(17), 4975-4978. https://doi.org/10.1016/j.bmcl.2013.06.065

Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities. / Nair, Padma; Yamamoto, Takashi; Largent-Milnes, Tally M. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 17, 01.09.2013, p. 4975-4978.

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

Nair, P, Yamamoto, T, Largent-Milnes, TM, Cowell, S, Kulkarni, V, Moye, S, Navratilova, E, Davis, P, Ma, SW, Vanderah, TW, Lai, J, Porreca, F & Hruby, VJ 2013, 'Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities', Bioorganic and Medicinal Chemistry Letters, vol. 23, no. 17, pp. 4975-4978. https://doi.org/10.1016/j.bmcl.2013.06.065

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title = "Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities",

abstract = "The optimization and truncation of our lead peptide-derived ligand TY005 possessing eight amino-acid residues was performed. Among the synthesized derivatives, NP30 (Tyr1-DAla2-Gly3-Phe 4-Gly5-Trp6-O-[3′,5′-Bzl(CF 3)2]) showed balanced and potent opioid agonist as well as substance P antagonist activities in isolated tissue-based assays, together with significant antinociceptive and antiallodynic activities in vivo.",

keywords = "Bifunctional compounds, NMR structure, Neutokinin-1 receptor antagonists, Opioid receptor agonists, Truncation of peptide sequence",

author = "Padma Nair and Takashi Yamamoto and Largent-Milnes, \{Tally M.\} and Scott Cowell and Vinod Kulkarni and Sharif Moye and Edita Navratilova and Peg Davis and Ma, \{Shou Wu\} and Vanderah, \{Todd W.\} and Josephine Lai and Frank Porreca and Hruby, \{Victor J\}",

note = "Funding Information: The work was supported by Grants from the USDHS, National Institute on Drug Abuse , DA-13449 and DA-06284 . We thank Dr. Yeon Sun Lee and Dr. Eva Varga for scientific discussion, and Ms. Magdalena Kaczmarska for culturing cells.",

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doi = "10.1016/j.bmcl.2013.06.065",

language = "English (US)",

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AU - Nair, Padma

AU - Yamamoto, Takashi

AU - Largent-Milnes, Tally M.

AU - Cowell, Scott

AU - Kulkarni, Vinod

AU - Moye, Sharif

AU - Navratilova, Edita

AU - Davis, Peg

AU - Ma, Shou Wu

AU - Vanderah, Todd W.

AU - Lai, Josephine

AU - Porreca, Frank

AU - Hruby, Victor J

N1 - Funding Information: The work was supported by Grants from the USDHS, National Institute on Drug Abuse , DA-13449 and DA-06284 . We thank Dr. Yeon Sun Lee and Dr. Eva Varga for scientific discussion, and Ms. Magdalena Kaczmarska for culturing cells.

PY - 2013/9/1

Y1 - 2013/9/1

N2 - The optimization and truncation of our lead peptide-derived ligand TY005 possessing eight amino-acid residues was performed. Among the synthesized derivatives, NP30 (Tyr1-DAla2-Gly3-Phe 4-Gly5-Trp6-O-[3′,5′-Bzl(CF 3)2]) showed balanced and potent opioid agonist as well as substance P antagonist activities in isolated tissue-based assays, together with significant antinociceptive and antiallodynic activities in vivo.

AB - The optimization and truncation of our lead peptide-derived ligand TY005 possessing eight amino-acid residues was performed. Among the synthesized derivatives, NP30 (Tyr1-DAla2-Gly3-Phe 4-Gly5-Trp6-O-[3′,5′-Bzl(CF 3)2]) showed balanced and potent opioid agonist as well as substance P antagonist activities in isolated tissue-based assays, together with significant antinociceptive and antiallodynic activities in vivo.

KW - Bifunctional compounds

KW - NMR structure

KW - Neutokinin-1 receptor antagonists

KW - Opioid receptor agonists

KW - Truncation of peptide sequence

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JO - Bioorganic and Medicinal Chemistry Letters

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Truncation of the peptide sequence in bifunctional ligands with mu and delta opioid receptor agonist and neurokinin 1 receptor antagonist activities

Abstract

Keywords

ASJC Scopus subject areas

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