Legume cyclotides shed light on the genetic origin of knotted circular proteins

Camarero, Julio A.

doi:10.1073/pnas.1107849108

Cited by 15 publications

(13 citation statements)

References 22 publications

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“…[6] Cyclotides are fascinating micro-proteins (≈30 residues long) present in several families of plants. [7] Naturally-occurring cyclotides display numerous biological properties such as protease inhibitory, anti-microbial, insecticidal, cytotoxic, anti-HIV and hormone-like activities.…”

Section: Introductionmentioning

confidence: 99%

Cyclotides: Overview and Biotechnological Applications

Gould

Camarero

2017

ChemBioChem

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Cyclotides are globular microproteins with a unique head-to-tail cyclized backbone, stabilized by three disulfide bonds forming a cystine knot. This unique circular backbone topology and knotted arrangement of three disulfide bonds makes them exceptionally stable to chemical, thermal and biological degradation compared to other peptides of similar size. In addition, cyclotides have been shown to be highly tolerant to sequence variability aside from the conserved residues forming the cystine knot. Cyclotides can also cross cellular membranes and are able to modulate intracellular protein-protein interactions both in vitro and in vivo. All these features make cyclotides appear as highly promising leads or frameworks for the design of peptide-based diagnostic and therapeutic tools. This article provides an overview on cyclotides and their applications as molecular imaging agents and peptide-based therapeutics.

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Section: Introductionmentioning

confidence: 99%

Cyclotides: Overview and Biotechnological Applications

Gould

Camarero

2017

ChemBioChem

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confidence: 99%

“…[1,2] Notably,inparticular, atopologically intriguing,prototypical non-planar K 3,3 -graph construction, which cannot be embedded in the plane in such away that its edges intersect only at their endpoints,h as recently been identified in cyclotides from diverse origins. [1,3] Thee ffective and programmed folding by synthetic polymers into designated multicyclic forms,o nt he other hand, has been an ongoing challenge in polymer chemistry. [4] We have developed an electrostatic self-assembly and covalent fixation (ESA-CF) method [5] for the programmed polymer folding in which linear, star, and other branched telechelic precursors having cyclic ammonium salt groups carrying plurifunctional carboxylate counteranions were employed to form polymeric self-assemblies as key intermediates.T he three forms of dicyclicc onstructions,t hat is, q (fused), 8( spiro), and manacle (bridged), as well as at refoil (spiro-tricyclic) construction have been effectively produced through the ESA-CF process.…”

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Folding Construction of a Pentacyclic Quadruply fused Polymer Topology with Tailored kyklo‐Telechelic Precursors

2015

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Ap entacyclic quadruply fused polymer topology has been constructed for the first time through alkyne-azide addition (click)a nd olefin metathesis (clip) reactions in conjunction with an electrostatic self-assembly and covalent fixation (ESA-CF) process.T hus,aspiro-type,t andem tetracyclic poly(tetrahydrofuran), poly(THF), precursor having two allyloxy groups at the opposite positions of the four ring units was prepared by the click-linking of one unit of an eightshaped precursor having alkyne groups at the opposite positions with two units of as ingle-cyclic counterpart having an azide and an alkene group at the opposite positions.B oth are obtainable through ESA-CF.T he subsequent metathesis clip-folding of the tetracyclic precursor could affordapentacyclic quadruply fused polymer product, of "shippo" form, in 19 %y ield.The programmed folding of polymer molecules,w hich is widely observed in diverse biopolymer events including DNA packaging and protein 3D structure formation, has also been highlighted in av ariety of cyclic peptides,c yclotides,c onstructing fused multicyclic structures formed through the intramolecular SÀSb ridging with cysteine residues,t obe crucial for their extraordinary stability and bioactivity. [1,2] Notably,inparticular, atopologically intriguing,prototypical non-planar K 3,3 -graph construction, which cannot be embedded in the plane in such away that its edges intersect only at their endpoints,h as recently been identified in cyclotides from diverse origins. [1,3] Thee ffective and programmed folding by synthetic polymers into designated multicyclic forms,o nt he other hand, has been an ongoing challenge in polymer chemistry. [4] We have developed an electrostatic self-assembly and covalent fixation (ESA-CF) method [5] for the programmed polymer folding in which linear, star, and other branched telechelic precursors having cyclic ammonium salt groups carrying plurifunctional carboxylate counteranions were employed to form polymeric self-assemblies as key intermediates.T he three forms of dicyclicc onstructions,t hat is, q (fused), 8( spiro), and manacle (bridged), as well as at refoil (spiro-tricyclic) construction have been effectively produced through the ESA-CF process. [5,6] Ac lass of fused multicyclic polymer topologies,r ather than their spiro and bridged counterparts,a re particularly attracting not only by their relevance to their programmed folding of cyclotides but also from the significanse of topological geometry conjectures [5,7] (Scheme 1). Thus,atetracyclic triply fused macromolecular K 3,3 -graph has been constructed through the ESA-CF method using au niformsize dendritic polymer precursor having six cyclic ammonium salt end groups carrying two units of at rifunctional carboxylate counteranions,a nd subsequent covalent conversion by the ring-opening reaction of cyclic ammonium salt groups at an elevated temperature under dilution.[8]Moreover,atandem alkyne-azide addition (click) and olefin metathesis (clip) reaction in conjunction with the ESA-CF proces...

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“…with most identified in the Rubiaceae, Violaceae [47,48] and Fabaceae families [49][50][51][52] (Table 1) whilst others have been recently reported in the Cucurbitaceae [48,53], Solanaceae [54], Poaceae [55] and Apocynaceae families [47]. Kalata B2 (net charge -1) is generally taken as the prototypic member of AHDPs in cylotides [23,27] and was first reported in the early 1970s when it was identified in Oldenlandia affinis of the Rubiaceae (Table 1), which is widely dispersed over tropical Africa and is also found in tropical Asia [56][57][58].…”

Section: Ahdps From Cyclotidesmentioning

confidence: 99%

Anionic Host Defence Peptides from the Plant Kingdom: Their Anticancer Activity and Mechanisms of Action

Harris¹,

Prabhu²,

Dennison³

et al. 2016

PPL

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Abstract:It is becoming increasingly clear that plants ranging across the plant kingdom produce anionic host defence peptides (AHDPs) with potent activity against a wide variety of human cancers cells. In general, this activity involves membrane partitioning by AHDPs, which leads to membranolysis and / or internalization to attack intracellular targets such as DNA. Several models have been proposed to describe these events including: the toroidal pore and Shai-Matsuzaki-Huang mechanisms but, in general, the mechanisms underpinning the membrane interactions and anticancer activity of these peptides are poorly understood. Plant AHDPs with anticancer activity can be conveniently discussed with reference to two groups: cyclotides, which possess cyclic molecules stabilized by cysteine knot motifs, and other ADHPs that adopt extended andhelical conformations. Here, we review research into the anticancer action of these two groups of peptides along with current understanding of the mechanisms underpinning this action.

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Legume cyclotides shed light on the genetic origin of knotted circular proteins

Cited by 15 publications

References 22 publications

Cyclotides: Overview and Biotechnological Applications

Cyclotides: Overview and Biotechnological Applications

Folding Construction of a Pentacyclic Quadruply fused Polymer Topology with Tailored kyklo‐Telechelic Precursors

Anionic Host Defence Peptides from the Plant Kingdom: Their Anticancer Activity and Mechanisms of Action

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