TY - JOUR
T1 - Crystal structure of biphalin sulfate
T2 - A multireceptor opioid peptide
AU - Flippen-Anderson, J. L.
AU - Deschamps, J. R.
AU - George, C.
AU - Hruby, V. J.
AU - Misicka, A.
AU - Lipkowski, A. W.
PY - 2002
Y1 - 2002
N2 - Biphalin is a dimeric opioid peptide, composed of two tetrapeptides connected 'tail-to-tail', that exhibits a high affinity for all three opioid receptor types (i.e. μ, δ and κ). This study presents the X-ray crystal structure of biphalin sulfate and compares it to other opioids that interact with the same biological targets. Both halves of the molecule have a folded backbone conformation but differ significantly from one another. Residues 1-4 in biphalin, which compare well with the δ selective opioid peptide DADLE, fold into a random coil. Residues 5-8, which can be fit to the μ selective peptide D-TIPP-NH2, exhibit a fairly normal type III′ β bend. Biphalin also exhibits structural similarities with two naltrexone analogs, naltrexonazine and norbinaltorphamine, that are specific to μ and κ receptor sites.
AB - Biphalin is a dimeric opioid peptide, composed of two tetrapeptides connected 'tail-to-tail', that exhibits a high affinity for all three opioid receptor types (i.e. μ, δ and κ). This study presents the X-ray crystal structure of biphalin sulfate and compares it to other opioids that interact with the same biological targets. Both halves of the molecule have a folded backbone conformation but differ significantly from one another. Residues 1-4 in biphalin, which compare well with the δ selective opioid peptide DADLE, fold into a random coil. Residues 5-8, which can be fit to the μ selective peptide D-TIPP-NH2, exhibit a fairly normal type III′ β bend. Biphalin also exhibits structural similarities with two naltrexone analogs, naltrexonazine and norbinaltorphamine, that are specific to μ and κ receptor sites.
KW - Agonist
KW - Analgesic
KW - Biphalin
KW - Conformation
KW - Neuropeptide
KW - Opioid receptor ligand
KW - X-ray diffraction
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U2 - 10.1046/j.1397-002x.2001.10967.x
DO - 10.1046/j.1397-002x.2001.10967.x
M3 - Article
C2 - 11985706
AN - SCOPUS:0036201028
SN - 1747-0277
VL - 59
SP - 123
EP - 133
JO - Chemical Biology and Drug Design
JF - Chemical Biology and Drug Design
IS - 3
ER -