Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH2Br) ([Phe(p-bromoacetamide)4]TIPP), a potent affinity label for δ opioid receptors

Vivek Kumar; Thomas F. Murray; Jane V. Aldrich

doi:10.1021/jm020290p

Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH₂Br) ([Phe(p-bromoacetamide)⁴]TIPP), a potent affinity label for δ opioid receptors

Vivek Kumar, Thomas F. Murray, Jane V. Aldrich

Research output: Contribution to journal › Article

9 Citations (Scopus)

Abstract

Derivatives of the δ opioid receptor selective peptide Tyr-Tic-Phe-Phe-OH (TIPP) containing a p-bromoacetamide moiety on the phenyl ring of Phe³ or Phe⁴ were prepared by solid phase synthesis. [Phe(p-NHCOCH₂Br)⁴]TIPP exhibited high affinity for cloned δ receptors (IC₅₀ = 5.4 nM), and incubation with only 2.5 nM resulted in 85% wash resistant inhibition of radioligand binding to δ receptors. Therefore, this peptide is a potent affinity label for further study of δ opioid receptors.

Original language	English
Pages (from-to)	3820-3823
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	45
Issue number	18
DOIs	https://doi.org/10.1021/jm020290p
State	Published - Aug 29 2002
Externally published	Yes

Fingerprint

phenylalanylphenylalanine

Affinity Labels

Tics

Solid-Phase Synthesis Techniques

Opioid Receptors

Peptides

Inhibitory Concentration 50

Derivatives

tyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl-phenylalanyl-4-bromoacetamidophenylalanine

All Science Journal Classification (ASJC) codes

Organic Chemistry

Cite this

Kumar, V., Murray, T. F., & Aldrich, J. V. (2002). Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH₂Br) ([Phe(p-bromoacetamide)⁴]TIPP), a potent affinity label for δ opioid receptors. Journal of Medicinal Chemistry, 45(18), 3820-3823. https://doi.org/10.1021/jm020290p

Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH₂Br) ([Phe(p-bromoacetamide)⁴]TIPP), a potent affinity label for δ opioid receptors. / Kumar, Vivek; Murray, Thomas F.; Aldrich, Jane V.

In: Journal of Medicinal Chemistry, Vol. 45, No. 18, 29.08.2002, p. 3820-3823.

Research output: Contribution to journal › Article

Kumar, V, Murray, TF & Aldrich, JV 2002, 'Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH₂Br) ([Phe(p-bromoacetamide)⁴]TIPP), a potent affinity label for δ opioid receptors', Journal of Medicinal Chemistry, vol. 45, no. 18, pp. 3820-3823. https://doi.org/10.1021/jm020290p

Kumar V, Murray TF, Aldrich JV. Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH₂Br) ([Phe(p-bromoacetamide)⁴]TIPP), a potent affinity label for δ opioid receptors. Journal of Medicinal Chemistry. 2002 Aug 29;45(18):3820-3823. https://doi.org/10.1021/jm020290p

Kumar, Vivek ; Murray, Thomas F. ; Aldrich, Jane V. / Solid phase synthesis and evaluation of Tyr-Tic-Phe-Phe(p-NHCOCH₂Br) ([Phe(p-bromoacetamide)⁴]TIPP), a potent affinity label for δ opioid receptors. In: Journal of Medicinal Chemistry. 2002 ; Vol. 45, No. 18. pp. 3820-3823.

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abstract = "Derivatives of the δ opioid receptor selective peptide Tyr-Tic-Phe-Phe-OH (TIPP) containing a p-bromoacetamide moiety on the phenyl ring of Phe3 or Phe4 were prepared by solid phase synthesis. [Phe(p-NHCOCH2Br)4]TIPP exhibited high affinity for cloned δ receptors (IC50 = 5.4 nM), and incubation with only 2.5 nM resulted in 85{\%} wash resistant inhibition of radioligand binding to δ receptors. Therefore, this peptide is a potent affinity label for further study of δ opioid receptors.",

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10.1021/jm020290p