Synthesis and pharmacological properties of a new fluorescent opioid peptide analog

Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity stu...
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Autor*in:	Lukowiak, Monika [verfasserIn] Kosson, Piotr Hennink, Wim E. Lipkowski, Andrzej W.

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2009

Anmerkung:	© Maj Institute of Pharmacology, Polish Academy of Sciences 2009

Übergeordnetes Werk:	Enthalten in: Pharmacological reports - Heidelberg : Springer Nature, 1998, 61(2009), 4 vom: Juli, Seite 727-731
Übergeordnetes Werk:	volume:61 ; year:2009 ; number:4 ; month:07 ; pages:727-731

Links:	Volltext

DOI / URN:	10.1016/S1734-1140(09)70126-4

Katalog-ID:	SPR03887721X

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520			\|a Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs.
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700	1		\|a Hennink, Wim E. \|4 aut
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912			\|a GBV_ILN_150
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912			\|a GBV_ILN_206
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912			\|a GBV_ILN_250
912			\|a GBV_ILN_281
912			\|a GBV_ILN_285
912			\|a GBV_ILN_293
912			\|a GBV_ILN_370
912			\|a GBV_ILN_602
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912			\|a GBV_ILN_702
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912			\|a GBV_ILN_2038
912			\|a GBV_ILN_2039
912			\|a GBV_ILN_2044
912			\|a GBV_ILN_2048
912			\|a GBV_ILN_2049
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912			\|a GBV_ILN_2064
912			\|a GBV_ILN_2065
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912			\|a GBV_ILN_2152
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912			\|a GBV_ILN_2190
912			\|a GBV_ILN_2232
912			\|a GBV_ILN_2336
912			\|a GBV_ILN_2446
912			\|a GBV_ILN_2470
912			\|a GBV_ILN_2472
912			\|a GBV_ILN_2507
912			\|a GBV_ILN_2522
912			\|a GBV_ILN_2548
912			\|a GBV_ILN_4012
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4046
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4125
912			\|a GBV_ILN_4126
912			\|a GBV_ILN_4242
912			\|a GBV_ILN_4246
912			\|a GBV_ILN_4249
912			\|a GBV_ILN_4251
912			\|a GBV_ILN_4305
912			\|a GBV_ILN_4306
912			\|a GBV_ILN_4307
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912			\|a GBV_ILN_4333
912			\|a GBV_ILN_4334
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912			\|a GBV_ILN_4338
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publishDate	2009
allfields	10.1016/S1734-1140(09)70126-4 doi (DE-627)SPR03887721X (SPR)S1734-1140(09)70126-4-e DE-627 ger DE-627 rakwb eng Lukowiak, Monika verfasserin aut Synthesis and pharmacological properties of a new fluorescent opioid peptide analog 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Maj Institute of Pharmacology, Polish Academy of Sciences 2009 Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. Kosson, Piotr aut Hennink, Wim E. aut Lipkowski, Andrzej W. aut Enthalten in Pharmacological reports Heidelberg : Springer Nature, 1998 61(2009), 4 vom: Juli, Seite 727-731 (DE-627)375964215 (DE-600)2129019-2 2299-5684 nnns volume:61 year:2009 number:4 month:07 pages:727-731 https://dx.doi.org/10.1016/S1734-1140(09)70126-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 61 2009 4 07 727-731
spelling	10.1016/S1734-1140(09)70126-4 doi (DE-627)SPR03887721X (SPR)S1734-1140(09)70126-4-e DE-627 ger DE-627 rakwb eng Lukowiak, Monika verfasserin aut Synthesis and pharmacological properties of a new fluorescent opioid peptide analog 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Maj Institute of Pharmacology, Polish Academy of Sciences 2009 Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. Kosson, Piotr aut Hennink, Wim E. aut Lipkowski, Andrzej W. aut Enthalten in Pharmacological reports Heidelberg : Springer Nature, 1998 61(2009), 4 vom: Juli, Seite 727-731 (DE-627)375964215 (DE-600)2129019-2 2299-5684 nnns volume:61 year:2009 number:4 month:07 pages:727-731 https://dx.doi.org/10.1016/S1734-1140(09)70126-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 61 2009 4 07 727-731
allfields_unstemmed	10.1016/S1734-1140(09)70126-4 doi (DE-627)SPR03887721X (SPR)S1734-1140(09)70126-4-e DE-627 ger DE-627 rakwb eng Lukowiak, Monika verfasserin aut Synthesis and pharmacological properties of a new fluorescent opioid peptide analog 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Maj Institute of Pharmacology, Polish Academy of Sciences 2009 Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. Kosson, Piotr aut Hennink, Wim E. aut Lipkowski, Andrzej W. aut Enthalten in Pharmacological reports Heidelberg : Springer Nature, 1998 61(2009), 4 vom: Juli, Seite 727-731 (DE-627)375964215 (DE-600)2129019-2 2299-5684 nnns volume:61 year:2009 number:4 month:07 pages:727-731 https://dx.doi.org/10.1016/S1734-1140(09)70126-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 61 2009 4 07 727-731
allfieldsGer	10.1016/S1734-1140(09)70126-4 doi (DE-627)SPR03887721X (SPR)S1734-1140(09)70126-4-e DE-627 ger DE-627 rakwb eng Lukowiak, Monika verfasserin aut Synthesis and pharmacological properties of a new fluorescent opioid peptide analog 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Maj Institute of Pharmacology, Polish Academy of Sciences 2009 Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. Kosson, Piotr aut Hennink, Wim E. aut Lipkowski, Andrzej W. aut Enthalten in Pharmacological reports Heidelberg : Springer Nature, 1998 61(2009), 4 vom: Juli, Seite 727-731 (DE-627)375964215 (DE-600)2129019-2 2299-5684 nnns volume:61 year:2009 number:4 month:07 pages:727-731 https://dx.doi.org/10.1016/S1734-1140(09)70126-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 61 2009 4 07 727-731
allfieldsSound	10.1016/S1734-1140(09)70126-4 doi (DE-627)SPR03887721X (SPR)S1734-1140(09)70126-4-e DE-627 ger DE-627 rakwb eng Lukowiak, Monika verfasserin aut Synthesis and pharmacological properties of a new fluorescent opioid peptide analog 2009 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Maj Institute of Pharmacology, Polish Academy of Sciences 2009 Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. Kosson, Piotr aut Hennink, Wim E. aut Lipkowski, Andrzej W. aut Enthalten in Pharmacological reports Heidelberg : Springer Nature, 1998 61(2009), 4 vom: Juli, Seite 727-731 (DE-627)375964215 (DE-600)2129019-2 2299-5684 nnns volume:61 year:2009 number:4 month:07 pages:727-731 https://dx.doi.org/10.1016/S1734-1140(09)70126-4 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_647 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4012 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4393 GBV_ILN_4700 AR 61 2009 4 07 727-731
language	English
source	Enthalten in Pharmacological reports 61(2009), 4 vom: Juli, Seite 727-731 volume:61 year:2009 number:4 month:07 pages:727-731
sourceStr	Enthalten in Pharmacological reports 61(2009), 4 vom: Juli, Seite 727-731 volume:61 year:2009 number:4 month:07 pages:727-731
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container_title	Pharmacological reports
authorswithroles_txt_mv	Lukowiak, Monika @@aut@@ Kosson, Piotr @@aut@@ Hennink, Wim E. @@aut@@ Lipkowski, Andrzej W. @@aut@@
publishDateDaySort_date	2009-07-01T00:00:00Z
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author	Lukowiak, Monika
spellingShingle	Lukowiak, Monika Synthesis and pharmacological properties of a new fluorescent opioid peptide analog
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topic_title	Synthesis and pharmacological properties of a new fluorescent opioid peptide analog
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title	Synthesis and pharmacological properties of a new fluorescent opioid peptide analog
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title_full	Synthesis and pharmacological properties of a new fluorescent opioid peptide analog
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author_browse	Lukowiak, Monika Kosson, Piotr Hennink, Wim E. Lipkowski, Andrzej W.
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title_sort	synthesis and pharmacological properties of a new fluorescent opioid peptide analog
title_auth	Synthesis and pharmacological properties of a new fluorescent opioid peptide analog
abstract	Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. © Maj Institute of Pharmacology, Polish Academy of Sciences 2009
abstractGer	Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. © Maj Institute of Pharmacology, Polish Academy of Sciences 2009
abstract_unstemmed	Abstract Biphalin, is a palindromic peptide [(Tyr-D-Ala-Gly-Phe-NH-)2] in which two opioid pharmacophores are connected “tail-to-tail.” This peptide displays a broad affinity for all opioid receptors (µ, δ and к) as well as exceptionally high antinociceptive activity. Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs. © Maj Institute of Pharmacology, Polish Academy of Sciences 2009
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title_short	Synthesis and pharmacological properties of a new fluorescent opioid peptide analog
url	https://dx.doi.org/10.1016/S1734-1140(09)70126-4
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Previous structure-activity studies demonstrated that one of the biphalin pharmacophores could be substituted with a hydrophobic group without significant loss of receptor affinity. This paper reports the pharmacological properties of a new analog in which one pharmacophore of biphalin was replaced with fluorescent 7-succinylamido-4-methyl-coumarin. The resulting compound displays an affinity for µ, opioid receptors that is a δ opioid receptor comparable to biphalin but with an affinity that is over a hundred times lower. This µ, opioid selective fluorescent peptide analog could be applied in pharmacokinetic and pharmacodynamic studies of biphalin related analogs.</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kosson, Piotr</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Hennink, Wim E.</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Lipkowski, Andrzej W.</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Pharmacological reports</subfield><subfield code="d">Heidelberg : Springer Nature, 1998</subfield><subfield code="g">61(2009), 4 vom: Juli, Seite 727-731</subfield><subfield code="w">(DE-627)375964215</subfield><subfield code="w">(DE-600)2129019-2</subfield><subfield code="x">2299-5684</subfield><subfield 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Synthesis and pharmacological properties of a new fluorescent opioid peptide analog

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