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aladan scanning: The structure-activity relationship of dynorphin A

Science China Chemistry 2009年第3期52卷 338-343页

作者： CHEN HeRu YANG Yang WENG JiangDuo Institute of Traditional Chinese Medicine and Natural Products Guangdong Province Key Laboratory of Pharmacodynamic Con-stituents of TCM and New Drugs ResearchJinan UniversityGuangzhou 510632China Department of Chemistry School of SciencesShantou UniversityShantou 515063China

An unnatural amino acid, β-[6′-(N, N-dimethyl)amino-2′-naphthoyl]alanine (Ald) showing polarity-sen sitive fluorescence characteristics, was synthesized. A thorough Ald-scan of dynorphin A (Dyn A), the putative endogenous ligand for κ opioid receptors, was then performed. Replacement of the amino acid residues in positions 5, 8, 10, 12 or 14 of Dyn A(1-13)-NH2 with Ald resulted in compounds that had almost equal κ binding affinity compared with that of the parent compound; on the other hand, substi-tution of residues in position 1 or 4 with Ald decreased κ-receptor binding affinity. These results indi-cate that Tyr and Phe in Dyn A are very important for maintaining its κ-opioid activity. Evidence from receptor binding assay clearly displays that [Ald5]Dyn A(1-13)-NH2 is a highly selective κ-opioid re-ceptor agonist. An evaluation of the interaction of Ald-containing Dyn A(1-13)-NH2 analogues with SDS and DPC micelles was also performed. Interestingly, [Ald1]Dyn A(1-13)-NH2 and [Ald4]Dyn A(1-13)-NH2 showed quite different fluorescence emission maxima in SDS and DPC micelles. This indicates that both peptides are sensitive to electronic properties of the polar surface of the micelles.

关键词： aladan dynorphin A fluorescent amino acid fluorescent peptide

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Syntheses of aladan and [Ald^6]loloatin C and Study on Their Fluorescent Properties

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Chinese Journal of Chemistry 2006年第10期24卷 1411-1417页

作者：陈河如郭锡坤钟宪斌 Department of Chemistry School of Sciences Shantou University Shantou Guangdong 515063 China Multidisciplanary Research Center Shantou University Shantou Guangdong 515063 China

aladan {β-[6＇-（N,N-dimethyl）amino-2＇-naphthoyl]alanine} and aladan-containing cyclodecapeptide [Ald^6]loloatin C were synthesized. The properties of their fluorescent behaviours both in aqueous buffer and micelles created by sodium dodecylsulfate （SDS） and dodecylphosphorylcholine （DPC） were further investigated. It was found that in either of micelle systems, [Ald^6]loloatin C possesses red-shift emission maximum wavelength and higher quantum yield. This property could be useful in the research of peptide-cell membrane interaction.

关键词： aladan loloatin C peptide antibiotic fluorescent amino acid fluorescent peptide

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