First Total Synthesis and Stereochemical Revision of Laxaphycin B and Its Extension to Lyngbyacyclamide A

Boyaud, France; Mahiout, Zahia; Lenoir, C.; Tang, Shoubin; Wdzieczak‐Bakala, Joanna; Witczak, Anne; Bonnard, Isabelle; Banaigs, Bernard; Ye, Tao; Inguimbert, Nicolas

doi:10.1021/ol401645m

Cited by 26 publications

(28 citation statements)

References 16 publications

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“…First crystals containing Zn were serendipitously obtained in the presence of a putative VEGFR ligand, the Laxaphycin B [13, 57] that revealed to be absent from the electron density. Other divalent metal cations were intentionally introduced.…”

Section: Methodsmentioning

confidence: 99%

“…Other divalent metal cations were intentionally introduced. Diffraction-quality crystals were optimized for three crystal forms: the first crystallized in the space group C 222 1 , from a drop containing 1 mM hVEGFR1d2, 0.1% (w/v) n-Dodecyl β-D-maltoside and 4 mM Laxaphycin B [57] in 5 mM HEPES-NaOH, pH 7.5, and a reservoir solution containing 18% (w/v) PEG 8000 and 100 mM HEPES-NaOH, pH 7.5. The second crystal form crystallized in the P 1 space group with 1 mM hVEGFR1d2 in 5 mM HEPES-NaOH, pH 7.0, 10 mM CoCl 2 , and a reservoir containing 100 mM Bis-Tris-HCl, pH 6.5, and 15% (w/v) PEG 3350.…”

Section: Methodsmentioning

confidence: 99%

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Biophysical Studies of the Induced Dimerization of Human VEGF Receptor 1 Binding Domain by Divalent Metals Competing with VEGF-A

Gaucher¹,

Reille-Seroussi²,

Gagey‐Eilstein³

et al. 2016

PLoS ONE

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Angiogenesis is tightly regulated through the binding of vascular endothelial growth factors (VEGFs) to their receptors (VEGFRs). In this context, we showed that human VEGFR1 domain 2 crystallizes in the presence of Zn2+, Co2+ or Cu2+ as a dimer that forms via metal-ion interactions and interlocked hydrophobic surfaces. SAXS, NMR and size exclusion chromatography analyses confirm the formation of this dimer in solution in the presence of Co2+, Cd2+ or Cu2+. Since the metal-induced dimerization masks the VEGFs binding surface, we investigated the ability of metal ions to displace the VEGF-A binding to hVEGFR1: using a competition assay, we evidenced that the metals displaced the VEGF-A binding to hVEGFR1 extracellular domain binding at micromolar level.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Biophysical Studies of the Induced Dimerization of Human VEGF Receptor 1 Binding Domain by Divalent Metals Competing with VEGF-A

Gaucher¹,

Reille-Seroussi²,

Gagey‐Eilstein³

et al. 2016

PLoS ONE

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“… Examples of natural sources peptides: Bergofungin D a peptaibols and ochratoxin A isolated from fungi. Lyngbyastatin‐10 and laxaphycin B are marine peptides produced by cyanobacteria. Non‐ribosomal amino acids, aminoisobutyric acid and the C‐terminal alcohol are highlighted respectively in blue, red, and green.…”

Section: Introductionmentioning

confidence: 90%

Straightforward strategy to substitute amide bonds by 1,2,3‐triazoles in peptaibols analogs using Aibψ[Tz]‐Xaa dipeptides

et al. 2015

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Structured peptides gained more attention over a decade because of their biological properties, biocompatibility and ability to act as modulators of protein/protein interactions, antibiotics, analgesics, immunosuppressants or as imaging agents to cite a few relevant applications. However, their poor bioavalability due in part to the susceptibility of the peptide bond to proteolytic cleavages often impaired their development and considerably limited their therapeutic use. To circumvent these problems, many efforts are undertaken to discover stable amide bond mimics resistant to proteolytic degradation. Among them the 1,2,3-triazole emerged as a highly stable analogue of the trans-peptide bond to generate bioactive peptides. Here we report a convenient approach to readily substitute amide bonds by triazole rings in Aib-containing peptides using Aibψ[Tz]-Xaa dipeptide-like units. We defined their application in solid phase synthesis and generated short model peptide sequences to study the impact of the triazole incorporation on their conformations in solution by circular dichroism and nuclear magnetic resonance spectroscopies.

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“…Compounds 121 and 122 show cytotoxicity against the growth of B16 melanoma cells with an IC 50 of 0.7 μM [85]. Total synthesis of 121 has been completed [86]. Pompanopeptin B ( 123 ) has been purified from Lyngbya confervoides from the coast of Florida [66].…”

Section: Cyclic Peptidesmentioning

confidence: 99%

New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade

Zhang

et al. 2017

Marine Drugs

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Marine cyanobacteria are significant sources of structurally diverse marine natural products with broad biological activities. In the past 10 years, excellent progress has been made in the discovery of marine cyanobacteria-derived peptides with diverse chemical structures. Most of these peptides exhibit strong pharmacological activities, such as neurotoxicity and cytotoxicity. In the present review, we summarized peptides isolated from marine cyanobacteria since 2007.

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First Total Synthesis and Stereochemical Revision of Laxaphycin B and Its Extension to Lyngbyacyclamide A

Cited by 26 publications

References 16 publications

Biophysical Studies of the Induced Dimerization of Human VEGF Receptor 1 Binding Domain by Divalent Metals Competing with VEGF-A

Biophysical Studies of the Induced Dimerization of Human VEGF Receptor 1 Binding Domain by Divalent Metals Competing with VEGF-A

Straightforward strategy to substitute amide bonds by 1,2,3‐triazoles in peptaibols analogs using Aibψ[Tz]‐Xaa dipeptides

New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade

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