Novel Cyclopeptides for the Design of MMP Directed Delivery Devices: A Novel Smart Delivery Paradigm

Moustoifa, El-Farouck; Alouini, Mohamed-Anis; Salaün, Arnaud; Berthelot, Thomas; Bartegi, Aghleb; Albenque-Rubio, Sandra; Déléris, Gérard

doi:10.1007/s11095-010-0164-0

Cited by 4 publications

(20 citation statements)

References 38 publications

(34 reference statements)

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“…This system has demonstrated its utility for measuring proteolysis by FRET-based follow-up in solution [32,48]. Peptide sequences developed in our previous work [20] are presented in Fig. 3.…”

Section: Resultsmentioning

confidence: 98%

“…3) were chosen from Nagase's work [49] coming sequences of natural protein cleavage sites of MMPs. We had previously studied [20] the behavior and selectivity of these sequences. In fact our choice of the cleavage sequences of MMP-1, -2, and -9 had been done in order to have selective cleavage for each synthetic peptide.…”

Section: Resultsmentioning

confidence: 99%

“…8, 9, and 10 were synthesized using a Fmoc strategy as described in our previous work [20]. A preloaded Fmoc-Ala-Wang resin (0.72 mmol/g) was used for the synthesis (0,25 mmol; 350 mg).…”

Section: Peptide Synthesismentioning

confidence: 99%

“…For measuring MMP activities, either simple techniques, generally with synthetic substrates, can be used or more cumbersome and complex methods using native or modified proteins, which are more difficult to use for screening MMP activities [18] but often closer to biological reality. Synthetic MMP substrates allow rapid and numerous assays to be performed [19,20]. Various liquid assays allowing detection of MMP activities are commercially available [21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

“…In an innovative approach to the successful design of specific MMP substrates, we previously synthesized fluorogenic (integrating FRET system by two coumarins) linear and cyclic MMP-1, -2, and -9 substrates [20]. In fact, novel synthetic cyclo-peptides proved to be specifically cleaved by only one or at least selectively by one MMP.…”

Section: Introductionmentioning

confidence: 99%

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Design, characterization, and evaluation of peptide arrays allowing the direct monitoring of MMP activities

et al. 2012

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Characterization of matrix metalloprotease (MMP) activities is of increasing interest for cancer prognosis or treatment follow-up. Indeed, MMP-1, -2 and -9 are widely involved in the growth of many tumors and progression steps such as angiogenesis, invasion, and metastasis. Fluorogenic peptide MMP substrates were previously synthesized with the aim of detecting MMP activities. One of their drawbacks is their limited solubility in biological media. Grafting them onto a solid support represented a novel way to yield efficient analysis devices whilst at the same time decreasing the quantities of peptides used. Novel peptide arrays were designed in order to detect MMP activities in biological fluids. Silicon plates were used as the solid support for the design of these novel tools. These were functionalized by organic self-assembled monolayers (SAMs) on which fluorogenic peptides were covalently coupled. SAM and peptide grafting on silicon plates were confirmed by epifluorescence, ellipsometry, and FT-IR analysis. Enzymatic assays were monitored by fluorescence spectrometry and showed that immobilized linear peptides were recognized and cleaved by MMPs.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

“…8, 9, and 10 were synthesized using a Fmoc strategy as described in our previous work [20]. A preloaded Fmoc-Ala-Wang resin (0.72 mmol/g) was used for the synthesis (0,25 mmol; 350 mg).…”

Section: Peptide Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, characterization, and evaluation of peptide arrays allowing the direct monitoring of MMP activities

et al. 2012

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Interaction of Fluorescently Labeled Triethyleneglycol and Peptide Derivatives with β‐Cyclodextrin

Alouini¹,

Moustoifa²,

Rubio-Albenque³

et al. 2014

ChemPhysChem

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A triethyleneglycol (TEG) chain, a linear peptide, and a cyclic peptide labeled with 7-methoxycoumarin-3-carboxylic acid (MC) and 7-diethylaminocoumarin-3-carboxylic acid (DAC) were used to thoroughly study Förster resonance energy transfer (FRET) in inclusion complexes. (1) H NMR evidence was given for the formation of a 1:1 inclusion complex between β-cyclodextrin (β-CD) and the fluorophore moieties of model compounds. The binding constant was 20 times higher for DAC than for MC derivatives. Molecular modeling provided additional information. The UV/Vis absorption and fluorescence properties were studied and the energy transfer process was quantified. Fluorescence quenching was particularly strong for the peptide derivatives. The presence of β-CDs reduced the FRET efficiency slightly. Dye-labeled peptide derivatives can thus be used to form inclusion complexes with β-CDs and retain most of their FRET properties. This paves the way for their subsequent use in analytical devices that are designed to measure the activity of matrix metalloproteinases.

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Supramolecular Peptide/Surface Assembly for Monitoring Proteinase Activity and Cancer Diagnosis

Soum

Rubio-Albenque

Fery–Forgues

et al. 2015

ACS Appl. Mater. Interfaces

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Matrix metalloproteinases (MMP) are a family of proteolytic enzymes, the expression of which in a key step of tumor progression has recently been better defined. The overexpression of one or more MMPs is thus common among malignant tumors. It may characterize tumor progression and help predict its response to chemotherapy. Consequently, the development of a device for measuring MMP activities is an important challenge for diagnosis and prognosis. In this study, we describe an innovative supramolecular peptide/surface assembly for screening MMP activities. This sensor was used to discriminate various MMP activities and to distinguish between invasive and noninvasive cancerous cell suspensions. Our results confirm the proof-of-concept of a powerful tool for the determination of the tumor aggressiveness and a technical building block for future development of MMP lab-on-chip devices.

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Novel Cyclopeptides for the Design of MMP Directed Delivery Devices: A Novel Smart Delivery Paradigm

Abstract: These original derivatives could allow the design of MMP-controlled delivery devices, the specificity of which will be retained in complex biological media and in vivo.

Cited by 4 publications

References 38 publications

Design, characterization, and evaluation of peptide arrays allowing the direct monitoring of MMP activities

Design, characterization, and evaluation of peptide arrays allowing the direct monitoring of MMP activities

Interaction of Fluorescently Labeled Triethyleneglycol and Peptide Derivatives with β‐Cyclodextrin

Supramolecular Peptide/Surface Assembly for Monitoring Proteinase Activity and Cancer Diagnosis

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