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Journal articles
Solid phase synthesis of a redox delivery system with the aim of targeting peptides into the brain.
Claudine Patteux
1
Lénaïg Foucout
1
Pierre Bohn
2, *
Georges Dupas
1
Jérôme Leprince
3
Marie-Christine Tonon
3
Bénédicte Dehouck
4
Francis Marsais
1
Cyril Papamicaël
1
Vincent Levacher
1
Claudine Patteux 1
Author
Lénaïg Foucout 1
Author
Pierre Bohn 2
Correspondent author
Georges Dupas 1
Author
Jérôme Leprince 3
Author IdHAL : jerome-leprince ORCID : https://orcid.org/0000-0002-7814-9927
Marie-Christine Tonon 3
Author
Bénédicte Dehouck 4
Author
Francis Marsais 1
Author
Cyril Papamicaël 1
Author
Vincent Levacher 1
Author IdHAL : vincent-levacher ORCID : https://orcid.org/0000-0002-6429-1965
1
AHHBO - Asymétrie, hétérocycles, hétérochimie et bio-organique (IRCOF Place Emile Blondel - BP 08 76131 MONT ST AIGNAN CEDEX - France)
- UNIROUEN - Université de Rouen Normandie (1, rue Thomas Becket 76821 Mont-Saint-Aignan Cedex - France)
- NU - Normandie Université (Esplanade de la Paix - CS 14032 - 14032 Caen Cedex 5 - France)
- INSA Rouen Normandie - Institut national des sciences appliquées Rouen Normandie (Avenue de l’Université 76801 Saint-Étienne-du-Rouvray Cedex - France)
- NU - Normandie Université (Esplanade de la Paix - CS 14032 - 14032 Caen Cedex 5 - France)
- INSA - Institut National des Sciences Appliquées (France)
- CNRS - Centre National de la Recherche Scientifique : UMR6014 (France)
2
LITIS - Laboratoire d'Informatique, de Traitement de l'Information et des Systèmes (Avenue de l'Université 76800 Saint-Étienne-du-Rouvray - France)
- ULH - Université Le Havre Normandie (25 rue Philippe Lebon - BP 1123 - 76063 Le Havre Cedex France - France)
- NU - Normandie Université (Esplanade de la Paix - CS 14032 - 14032 Caen Cedex 5 - France)
- UNIROUEN - Université de Rouen Normandie : EA4108 (1, rue Thomas Becket 76821 Mont-Saint-Aignan Cedex - France)
- NU - Normandie Université (Esplanade de la Paix - CS 14032 - 14032 Caen Cedex 5 - France)
- INSA Rouen Normandie - Institut national des sciences appliquées Rouen Normandie (Avenue de l’Université 76801 Saint-Étienne-du-Rouvray Cedex - France)
- NU - Normandie Université (Esplanade de la Paix - CS 14032 - 14032 Caen Cedex 5 - France)
- INSA - Institut National des Sciences Appliquées (France)
3
Neuroendocrinologie cellulaire et moléculaire (Universite de Rouen 76821 MONT-SAINT-AIGNAN CEDEX - France)
- UNIROUEN - Université de Rouen Normandie : U413 (1, rue Thomas Becket 76821 Mont-Saint-Aignan Cedex - France)
- NU - Normandie Université (Esplanade de la Paix - CS 14032 - 14032 Caen Cedex 5 - France)
- INSERM - Institut National de la Santé et de la Recherche Médicale : U413 (101, rue de Tolbiac, 75013 Paris - France)
4
LBHE - Laboratoire de Physiopathologie de la Barrière Hémato-Encéphalique (Faculté des Sciences « Jean Perrin » Rue Jean Souvraz - SP 18 62307 Lens cedex - France)
- UA - Université d'Artois : EA2465 (9 rue du Temple - BP 10665 - 62030 Arras cedex - France)
Abstract : A solid phase approach for the preparation of peptides attached to a redox chemical delivery system derived from stable annulated NADH models is reported. The synthesis starts with the grafting on a Merrifield resin of quinoline 4b, precursor of the redox carrier. From the resulting quinoline supported resin 4d, the stepwise SPPS of both octapeptide OP (RPGLLDLK) and octadecaneuropeptide ODN (QATVGDVNTDRPGLLDLK), two neuropeptides exhibiting anorexigenic effects, was successfully achieved by conventional methods. Quaternization of the quinoline moiety prior to cleavage of the modified OP and ODN peptides from the resin, led to the expected quinolinium salt 8a and 8b respectively linked to OP or ODN peptides. Finally, the reduction with NaBH4 monitored by UV-vis, provided the desired annulated NADH models as peptides carriers with either the OP (11a,b) or ODN (12a,b) moiety.
Document type :
Journal articles
Complete list of metadatas
https://www.hal.inserm.fr/inserm-00475858
Contributor : Céline Breton <>
Submitted on : Friday, April 23, 2010 - 11:00:57 AM
Last modification on : Wednesday, March 25, 2020 - 3:43:17 PM
Long-term archiving on: : Wednesday, November 30, 2016 - 5:11:10 PM
Contributor : Céline Breton <>
Submitted on : Friday, April 23, 2010 - 11:00:57 AM
Last modification on : Wednesday, March 25, 2020 - 3:43:17 PM
Long-term archiving on: : Wednesday, November 30, 2016 - 5:11:10 PM
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Identifiers
- HAL Id : inserm-00475858, version 1
- DOI : 10.1039/b516737j
- PUBMED : 16493464
Collections
UNIV-ARTOIS | CNRS | LITIS | COMUE-NORMANDIE | INC-CNRS | INSA-ROUEN | UNIROUEN | UNILEHAVRE | INSA-GROUPE
Citation
Claudine Patteux, Lénaïg Foucout, Pierre Bohn, Georges Dupas, Jérôme Leprince, et al.. Solid phase synthesis of a redox delivery system with the aim of targeting peptides into the brain.. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2006, 4 (5), pp.817-25. ⟨10.1039/b516737j⟩. ⟨inserm-00475858⟩
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