Structural properties and photophysical behavior of conformationally constrained hexapeptides functionalized with a new fluorescent analog of tryptophan and a nitroxide radical quencher

Venanzi, Mariano; Valeri, Alessandro; Palleschi, Antonio; Stella, Lorenzo; Moröder, Luis; Formaggio, Fernando; Toniolo, Claudio; Pispisa, B.

doi:10.1002/bip.20110

Cited by 20 publications

(14 citation statements)

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“…Mutation of Trp to AzAla has been shown to have a minimal effect on efficacy of short peptides targeting GPCR receptors in cell assays, 13 but the biophysical characterization of this probe was limited to studies of its interaction with synthetically introduced free radicals. 14–16 Here we demonstrate that AzAla’s insensitivity to the environment allows for investigation of biophysical phenomena by via a structurally conservative, single fluorescent probe, which does not require additional functionalization. Together with AzAla’s similarity to Trp, it provides a powerful chemical biology tool for looking at protein-protein interactions.…”

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confidence: 73%

Painting proteins blue: β-(1-azulenyl)-l-alanine as a probe for studying protein–protein interactions

et al. 2013

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confidence: 73%

Painting proteins blue: β-(1-azulenyl)-l-alanine as a probe for studying protein–protein interactions

et al. 2013

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“…The results confirmed previous findings showing that Afc may adopt either a fully extended or a turn conformation. In another study, Venanzi et al (2004) used FTIR, NMR, steady-state and time-resolved fluorescence, and molecular mechanics to investigate constrained hexapeptides containing a fluorescent analogue of tryptophan as well as TOAC.…”

Section: Synthetic Peptidesmentioning

confidence: 99%

The spin label amino acid TOAC and its uses in studies of peptides: chemical, physicochemical, spectroscopic, and conformational aspects

et al. 2012

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We review work on the paramagnetic amino acid 2,2,6,6-tetramethyl-N-oxyl-4-amino-4-carboxylic acid, TOAC, and its applications in studies of peptides and peptide synthesis. TOAC was the first spin label probe incorporated in peptides by means of a peptide bond. In view of the rigid character of this cyclic molecule and its attachment to the peptide backbone via a peptide bond, TOAC incorporation has been very useful to analyze backbone dynamics and peptide secondary structure. Many of these studies were performed making use of EPR spectroscopy, but other physical techniques, such as X-ray crystallography, CD, fluorescence, NMR, and FT-IR, have been employed. The use of double-labeled synthetic peptides has allowed the investigation of their secondary structure. A large number of studies have focused on the interaction of peptides, both synthetic and biologically active, with membranes. In the latter case, work has been reported on ligands and fragments of GPCR, host defense peptides, phospholamban, and β-amyloid. EPR studies of macroscopically aligned samples have provided information on the orientation of peptides in membranes. More recent studies have focused on peptide–protein and peptide–nucleic acid interactions. Moreover, TOAC has been shown to be a valuable probe for paramagnetic relaxation enhancement NMR studies of the interaction of labeled peptides with proteins. The growth of the number of TOAC-related publications suggests that this unnatural amino acid will find increasing applications in the future.

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“…Rueeger et al [15] reported that (5,6-dihydro-4H-3-thia-1-aza-benzo[e]azulen-2-yl) -piperidin-4-ylmethyl-amino and (4,5-dihydro-6-oxa -3-thia-1-azabenzo[e]azulen-2-yl)-piperidin-4 -ylmethyl-amino derivatives are capable of delivering potent and selective orally and centrally bioavailable NPY-Y5 receptor antagonists. The antioxidant activity of azulene derivatives may be due to their interaction with nitroxyl radicals [230,231]. Guaiazulene is used to prevent or treat any type of hypercholesterolemia, hyperlipidemia and any other lipid disorder, atherosclerosis or atheromatosis in humans and animals because it can induce a significant reduction of total cholesterol, total triglycerides and of LDL-cholesterol level but without showing any signs of toxicity or side effects on the tested animals [232].…”

Section: Azulene and Its Derivativesmentioning

confidence: 99%

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

Zhao

2007

CMC

113

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Tropone or tropolone and its derivatives (here together called troponoids) belong to a family of natural products with a seven-membered aromatic ring and various side groups. They are mainly synthesized by plants and fungi, and most troponoids play roles of antibacterial defenses in these organisms. With an increasingly severe situation of antibiotic resistant bacteria, as well as a requirement for antifungal medicines, troponoids have attracted extensive studies since they have powerful antibacterial and antifungal activity, particularly against antibiotic-resistant bacteria. In addition, many other biological activities such as antiviral, antitumor, antioxidant, anti-inflammatory, insecticidal, or enzyme inhibitor activities are associated with troponoids. After extensive studies in the 1960s-70s, interests in natural troponoids dedclined. However, chemical and biomedical studies on troponoids bloom again from the 1990s. To date great progress has been made with troponoid study in terms of identification of new natural troponoids, chemical synthesis and properties, biological activity, biosynthesis and metabolism. Particularly, bioassay-guided screening strategy and structure-activity relation-directed structure modification and drug design has resulted in the synthesis and discovery of many new derivatives. Many of them have great promise to be developed into new medicines for their potent and specific activities. This review presents the recent advances in troponoid studies and highlights multiple faceted biological activities of troponoids, as well as their relationships with chemical structures. Chemistry, biosynthesis, and production via biotechnology of troponoids are also briefly reviewed. Applications of troponoids in daily life, agriculture, medicine, and industry, and the related patents have been considered to further extend our understanding of the increasing impact of troponoids on humans.

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Structural properties and photophysical behavior of conformationally constrained hexapeptides functionalized with a new fluorescent analog of tryptophan and a nitroxide radical quencher

Cited by 20 publications

References 52 publications

Painting proteins blue: β-(1-azulenyl)-l-alanine as a probe for studying protein–protein interactions

Painting proteins blue: β-(1-azulenyl)-l-alanine as a probe for studying protein–protein interactions

The spin label amino acid TOAC and its uses in studies of peptides: chemical, physicochemical, spectroscopic, and conformational aspects

Plant Troponoids: Chemistry, Biological Activity, and Biosynthesis

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