title: Role of a Preorganized Scaffold Presenting Four Residues of a GM-3 Lactone Mimetic on Melanoma Progression.
abstract: Two tetravalent architectures, the glycocalix 7 and the RAFT 9, presenting four residues of a GM-3 ganglioside lactone mimetic, target the host compartment of melanoma and significantly abrogate the effect induced by cancer-associated fibroblasts (CAFs) contact + hypoxia in the motility and invasiveness of tumor cells. The data reported support the involvement of glycosphingolipids (GSLs) in hypoxia and show an interesting role played by compound 9 in targeting melanoma cells thereby interfering with melanoma progression. The unprecedented findings reported for the glycocluster 9 may contribute to the understanding of the critical and complex interactions between tumor cells and their local environment paving the way for new therapeutic agents.
authors.affiliation: Department of Chemistry "Ugo Schiff″, University of Florence , via della Lastruccia, 13 50019 Sesto F.no (FI), Italy.
authors.forename: Barbara
authors.initials: B
authors.lastname: Richichi
authors.affiliation: Department of Experimental and Clinical Biomedical Sciences, Biochemistry, Human Health Medical School, University of Florence , viale Morgagni 50, 50134 Firenze, Italy.
authors.forename: Giuseppina
authors.initials: G
authors.lastname: Comito
authors.affiliation: Université Grenoble-Alpes, and CNRS, DCM, 38000 Grenoble, France; Institut Universitaire de France, 103 Boulevard Saint-Michel, 75005 Paris, France.
authors.forename: Olivier
authors.initials: O
authors.lastname: Renaudet
authors.affiliation: Université Grenoble-Alpes, and CNRS, DCM , 38000 Grenoble, France.
authors.forename: Michele
authors.initials: M
authors.lastname: Fiore
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, Ecole Nationale Supérieure de Chimie de Montpellier , 8 Rue de l'Ecole Normale, 34296 Montpellier cedex 5, France.
authors.forename: A
authors.initials: A
authors.lastname: Marra
authors.affiliation: Core Research Laboratory, Istituto Toscano Tumori , viale Pieraccini, 6, 50139 Firenze, Italy.
authors.forename: B
authors.initials: B
authors.lastname: Stecca
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste , via L. Giorgieri 1, 34127 Trieste, Italy.
authors.forename: L
authors.initials: L
authors.lastname: Pasquato
authors.affiliation: Department of Experimental and Clinical Biomedical Sciences, Biochemistry, Human Health Medical School, University of Florence , viale Morgagni 50, 50134 Firenze, Italy.
authors.forename: P
authors.initials: P
authors.lastname: Chiarugi
authors.affiliation: Department of Chemistry "Ugo Schiff″, University of Florence, via della Lastruccia, 13 50019 Sesto F.no (FI), Italy; FiorGen, Polo Scientifico e Tecnologico, via Sacconi, 6 50019 Sesto F.no (FI), Italy.
authors.forename: C
authors.initials: C
authors.lastname: Nativi
keywords: Glycosides; mimetics; tumor antigen; tumor microenvironment
references.citation: Bioconjug Chem. 2010 Aug 18;21(8):1432-8
references.pmid: 20669938
references.citation: Nat Rev Cancer. 2004 Nov;4(11):839-49
references.pmid: 15516957
references.citation: Cancer Res. 2012 May 15;72(10):2473-80
references.pmid: 22414581
references.citation: Bioorg Med Chem. 2013 May 15;21(10):2756-63
references.pmid: 23583030
references.citation: Cancer Lett. 2012 Nov 1;324(1):31-41
references.pmid: 22659468
references.citation: Nat Rev Cancer. 2006 May;6(5):392-401
references.pmid: 16572188
references.citation: Angew Chem Int Ed Engl. 2014 Oct 27;53(44):11917-20
references.pmid: 25168881
references.citation: Proc Natl Acad Sci U S A. 2002 Jan 8;99(1):225-32
references.pmid: 11773621
references.citation: Bioessays. 1990 May;12(5):223-30
references.pmid: 1695095
references.citation: Clin Chem. 2013 Jan;59(1):85-93
references.pmid: 23193058
references.citation: Cell. 2011 Nov 23;147(5):992-1009
references.pmid: 22118458
references.citation: PLoS One. 2010 Jun 21;5(6):e11216
references.pmid: 20574522
references.citation: Biochim Biophys Acta. 2013 Dec;1836(2):321-35
references.pmid: 24183942
references.citation: Cancer Lett. 2013 Nov 28;341(1):80-96
references.pmid: 23376253
references.citation: Antioxid Redox Signal. 2013 Nov 20;19(15):1828-45
references.pmid: 23146119
references.citation: ChemMedChem. 2008 May;3(5):737-41
references.pmid: 18205167
references.citation: FEBS Lett. 2009 Feb 18;583(4):597-606
references.pmid: 19167383
references.citation: Cancer Metastasis Rev. 2012 Jun;31(1-2):195-208
references.pmid: 22101652
references.citation: Jpn J Cancer Res. 1989 Oct;80(10):988-92
references.pmid: 2533193
references.citation: Chembiochem. 2007 Sep 24;8(14):1646-9
references.pmid: 17705308
references.citation: Bioconjug Chem. 2005 Sep-Oct;16(5):1149-59
references.pmid: 16173792
references.citation: Histochem Cell Biol. 2008 Dec;130(6):1091-103
references.pmid: 18987874
references.citation: FEBS Lett. 2010 May 3;584(9):1901-6
references.pmid: 19874824
references.citation: Chem Soc Rev. 2013 Jun 7;42(11):4599-612
references.pmid: 23263159
references.citation: Cancer Metastasis Rev. 2010 Jun;29(2):351-78
references.pmid: 20386957