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Literature DB >> 24900366

Prodrugs of a CXC Chemokine-12 (CXCL12) Neutraligand Prevent Inflammatory Reactions in an Asthma Model in Vivo.

Vincent Gasparik¹, François Daubeuf¹, Muriel Hachet-Haas², François Rohmer¹, Patrick Gizzi², Jacques Haiech¹, Jean-Luc Galzi², Marcel Hibert¹, Dominique Bonnet¹, Nelly Frossard¹.

Abstract

Chalcone 4 (compound 1) is a small molecule that neutralizes the CXC chemokine CXCL12 and prevents it from acting on the CXCR4 and CXCR7 receptors. To overcome its poor solubility in aqueous buffers, we designed highly soluble analogues of compound 1, phosphate, l-seryl, and sulfate, all inactive by themselves on CXCL12 but when cleaved in vivo into 1, highly active locally at a low dose in a mouse airway hypereosinophilia model.

Entities: Chemical Disease Gene Species

Keywords: CXCL12 chemokine; CXCR4 receptor; GPCR; asthma; prodrug; solubility

Year: 2011 PMID： 24900366 PMCID： PMC4025865 DOI： 10.1021/ml200017d

Source DB: PubMed Journal: ACS Med Chem Lett ISSN： 1948-5875 Impact factor: 4.345

16 in total

Review 1. Structure, function, and inhibition of chemokines.

Authors: Elias J Fernandez; Elias Lolis
Journal: Annu Rev Pharmacol Toxicol Date: 2002 Impact factor: 13.820

2. Targeting SDF-1/CXCL12 with a ligand that prevents activation of CXCR4 through structure-based drug design.

Authors: Christopher T Veldkamp; Joshua J Ziarek; Francis C Peterson; Yu Chen; Brian F Volkman
Journal: J Am Chem Soc Date: 2010-06-02 Impact factor: 15.419

3. Synthesis of some pyrazole derivatives and preliminary investigation of their affinity binding to P-glycoprotein.

Authors: Fedele Manna; Franco Chimenti; Rossella Fioravanti; Adriana Bolasco; Daniela Secci; Paola Chimenti; Cristiano Ferlini; Giovanni Scambia
Journal: Bioorg Med Chem Lett Date: 2005-10-15 Impact factor: 2.823

4. AMD3465, a novel CXCR4 receptor antagonist, abrogates schistosomal antigen-elicited (type-2) pulmonary granuloma formation.

Authors: Jerry S Hu; Christine M Freeman; Valerie R Stolberg; Bo Chin Chiu; Gary J Bridger; Simon P Fricker; Nicholas W Lukacs; Stephen W Chensue
Journal: Am J Pathol Date: 2006-08 Impact factor: 4.307

5. Chromatographic Hydrophobicity Index by Fast-Gradient RP-HPLC: A High-Throughput Alternative to log P/log D.

Authors: K Valkó; C Bevan; D Reynolds
Journal: Anal Chem Date: 1997-06-01 Impact factor: 6.986

Review 6. Prodrugs--from serendipity to rational design.

Authors: Kristiina M Huttunen; Hannu Raunio; Jarkko Rautio
Journal: Pharmacol Rev Date: 2011-07-07 Impact factor: 25.468

7. A novel solution-stable, water-soluble prodrug type for drugs containing a hydroxyl or an NH-acidic group.

Authors: H Bundgaard; E Falch; E Jensen
Journal: J Med Chem Date: 1989-12 Impact factor: 7.446

8. AMD3100, a CxCR4 antagonist, attenuates allergic lung inflammation and airway hyperreactivity.

Authors: Nicholas W Lukacs; Aaron Berlin; Dominique Schols; Renato T Skerlj; Gary J Bridger
Journal: Am J Pathol Date: 2002-04 Impact factor: 4.307

9. Development of prodrug 4-chloro-3-(5-methyl-3-{[4-(2-pyrrolidin-1-ylethoxy)phenyl]amino}-1,2,4-benzotriazin-7-yl)phenyl benzoate (TG100801): a topically administered therapeutic candidate in clinical trials for the treatment of age-related macular degeneration.

Authors: Moorthy S S Palanki; Hideo Akiyama; Peter Campochiaro; Jianguo Cao; Chun P Chow; Luis Dellamary; John Doukas; Richard Fine; Colleen Gritzen; John D Hood; Steven Hu; Shu Kachi; Xinshan Kang; Boris Klebansky; Ahmed Kousba; Dan Lohse; Chi Ching Mak; Michael Martin; Andrew McPherson; Ved P Pathak; Joel Renick; Richard Soll; Naoyasu Umeda; Shiyin Yee; Katsutoshi Yokoi; Binqi Zeng; Hong Zhu; Glenn Noronha
Journal: J Med Chem Date: 2008-02-27 Impact factor: 7.446

Review 10. Neutralizing endogenous chemokines with small molecules. Principles and potential therapeutic applications.

Authors: Jean-Luc Galzi; Muriel Hachet-Haas; Dominique Bonnet; Francois Daubeuf; Sandra Lecat; Marcel Hibert; Jacques Haiech; Nelly Frossard
Journal: Pharmacol Ther Date: 2010-02-01 Impact factor: 12.310

10 in total

1. Pharmacological tools to mobilise mesenchymal stromal cells into the blood promote bone formation after surgery.

Authors: Tariq G Fellous; Andia N Redpath; Mackenzie M Fleischer; Sapan Gandhi; Samantha E Hartner; Michael D Newton; Moïra François; Suet-Ping Wong; Kate H C Gowers; Adam M Fahs; Daniel R Possley; Dominique Bonnet; Paula Urquhart; Anna Nicolaou; Kevin C Baker; Sara M Rankin
Journal: NPJ Regen Med Date: 2020-02-21

10. Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) In Vitro.

Authors: Katharina Schueller; Joachim Hans; Stefanie Pfeiffer; Jessica Walker; Jakob P Ley; Veronika Somoza
Journal: Molecules Date: 2020-03-18 Impact factor: 4.411

10 in total

Prodrugs of a CXC Chemokine-12 (CXCL12) Neutraligand Prevent Inflammatory Reactions in an Asthma Model in Vivo.

Review 1. Structure, function, and inhibition of chemokines.

2. Targeting SDF-1/CXCL12 with a ligand that prevents activation of CXCR4 through structure-based drug design.

3. Synthesis of some pyrazole derivatives and preliminary investigation of their affinity binding to P-glycoprotein.

4. AMD3465, a novel CXCR4 receptor antagonist, abrogates schistosomal antigen-elicited (type-2) pulmonary granuloma formation.

5. Chromatographic Hydrophobicity Index by Fast-Gradient RP-HPLC: A High-Throughput Alternative to log P/log D.

Review 6. Prodrugs--from serendipity to rational design.

7. A novel solution-stable, water-soluble prodrug type for drugs containing a hydroxyl or an NH-acidic group.

8. AMD3100, a CxCR4 antagonist, attenuates allergic lung inflammation and airway hyperreactivity.

9. Development of prodrug 4-chloro-3-(5-methyl-3-{[4-(2-pyrrolidin-1-ylethoxy)phenyl]amino}-1,2,4-benzotriazin-7-yl)phenyl benzoate (TG100801): a topically administered therapeutic candidate in clinical trials for the treatment of age-related macular degeneration.

Review 10. Neutralizing endogenous chemokines with small molecules. Principles and potential therapeutic applications.

1. Pharmacological tools to mobilise mesenchymal stromal cells into the blood promote bone formation after surgery.

2. Two distinct CXCR4 antagonists mobilize progenitor cells in mice by different mechanisms.

3. Design, Synthesis and Biological Evaluation of Prodrugs of 666-15 as Inhibitors of CREB-Mediated Gene Transcription.

4. Fragment-based optimization of small molecule CXCL12 inhibitors for antagonizing the CXCL12/CXCR4 interaction.

Review 5. The Prodrug Approach: A Successful Tool for Improving Drug Solubility.

Review 6. Chalcone Derivatives: Promising Starting Points for Drug Design.

7. Pharmacological tools to mobilise mesenchymal stromal cells into the blood promote bone formation after surgery.

8. An antedrug of the CXCL12 neutraligand blocks experimental allergic asthma without systemic effect in mice.

9. A strategy to discover decoy chemokine ligands with an anti-inflammatory activity.

10. Identification of Interleukin-8-Reducing Lead Compounds Based on SAR Studies on Dihydrochalcone-Related Compounds in Human Gingival Fibroblasts (HGF-1 cells) In Vitro.