Solid-phase syntheses of constrained RGD scaffolds and their binding to the αvβ3 integrin receptor

Royo, Míriam; Nest, Wim Van Den; Fresno, Montserrat del; Frieden, Ariadna; Yahalom, Dror; Rosenblatt, Michael; Chorev, Michael; Alberício, Fernando

doi:10.1016/s0040-4039(01)01510-6

Cited by 28 publications

(23 citation statements)

References 28 publications

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“…Two other cyclic RGD ligands containing a bifunctional diketopiperazine scaffold were reported in the literature,14 namely cyclo‐[aspartate‐(2 S ,4 S )‐4‐aminoproline] by Robinson and co‐workers,14a and cyclo‐(Asp‐Lys) by Albericio and co‐workers 14b. In both cases the diketopiperazine substituents in the 3,6‐positions were cis .…”

Section: Inhibition Of Biotinylated Vitronectin Binding To αVβ3 and αmentioning

confidence: 98%

Cyclic RGD‐Peptidomimetics Containing Bifunctional Diketopiperazine Scaffolds as New Potent Integrin Ligands

Ressurreição

Vidu

Civera

et al. 2009

Chemistry A European J

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The tripeptide sequence arginine-glycine-aspartate (RGD) has been identified as the common motif used by several endogenous ligands to recognise and bind a group of integrins, [1] including a V b 3 , a V b 5 , a 5 b 1 , which play key roles in angiogenesis, tumor progression and metastasis.[2] The context of the ligand RGD sequence (flanking residues, three-dimensional presentation) and individual features of the integrin binding pockets determine the recognition specificity and discrimination ability, that is, whether a productive interaction occurs. A major breakthrough for understanding this interaction came in 2002 from the X-ray structure determination of the complex of integrin a V b 3 with cyclo-[Arg-Gly-Asp-d-Phe-N(Me)-Val] (Cilengitide).[3] This potent a V b 3 ligand was developed by Kessler and co-workers, [4] and is currently in phase III clinical trials for patients with glioblastoma multiforme as an angiogenesisis inhibitor.

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Section: Inhibition Of Biotinylated Vitronectin Binding To αVβ3 and αmentioning

confidence: 98%

Cyclic RGD‐Peptidomimetics Containing Bifunctional Diketopiperazine Scaffolds as New Potent Integrin Ligands

Ressurreição

Vidu

Civera

et al. 2009

Chemistry A European J

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“…To avoid a nucleophilic attack of the free amino function leading to by-products, deprotection of the C-terminal carboxyl function must be carried out before the last Fmoc removal [45]. Allyl deprotection was then performed using Pd(PPh 3 ) 4 in CHCl 3 /AcOH/NMM (37 : 2 : 1), under anhydrous conditions (method 1).…”

Section: Syntheses Of Cyclo(xaa-arg-gly-asp) (7a-f)mentioning

confidence: 99%

On‐resin head‐to‐tail cyclization of cyclotetrapeptides: optimization of crucial parameters

Alcaro

Sabatino

Uziel

et al. 2003

Journal of Peptide Science

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Cyclotetrapeptides are constrained cyclic peptides whose synthesis is considered a difficult task. A methodology based on on-resin head-to-tail cyclization by anchoring the side chain of a trifunctional amino acid was investigated. A series of model cyclotetrapeptides containing the RGD sequence cyclo(Xaa-Arg-Gly-Asp) (Xaa = Ala, Phe, Phg, D-Ala, D-Phe, D-Phg) was synthesized with no cyclodimerization by-products. An evaluation and optimization study of all of the parameters directly involved in the ring closure was performed.

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“…The PAL linker has been mostly used to prepare heterocycles such as 1,4dihydropyridines 20 via Michael addition, secondary amines 21 after reductive alkylation (eq 3), diketopiperazines, 16 3,4dihydroquinazolines, 15 and 1,3,5-trisubstitued triazines. 13, 14 The PAL linker is also compatible with cross-coupling conditions such as N-arylation 6 of supported sulfonamides with boronic acids promoted by copper acetate (eq 4) and palladium-catalyzed amination 9 of 4-bromobenzonitrile (eq 5).…”

Section: -[(4-aminomethyl)-35-dimethoxyphenoxy]pentanoic Acidmentioning

confidence: 99%

5-[(4-Aminomethyl)-3,5-dimethoxyphenoxy]pentanoic Acid

Jacob

Bennett

2003

Encyclopedia of Reagents for Organic Synthesis

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Solid-phase syntheses of constrained RGD scaffolds and their binding to the αvβ3 integrin receptor

Cited by 28 publications

References 28 publications

Cyclic RGD‐Peptidomimetics Containing Bifunctional Diketopiperazine Scaffolds as New Potent Integrin Ligands

Cyclic RGD‐Peptidomimetics Containing Bifunctional Diketopiperazine Scaffolds as New Potent Integrin Ligands

On‐resin head‐to‐tail cyclization of cyclotetrapeptides: optimization of crucial parameters

5-[(4-Aminomethyl)-3,5-dimethoxyphenoxy]pentanoic Acid

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