{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:43:23Z","timestamp":1760550203986,"version":"build-2065373602"},"reference-count":115,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2017,2,9]],"date-time":"2017-02-09T00:00:00Z","timestamp":1486598400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002809","name":"Generalitat de Catalunya","doi-asserted-by":"publisher","award":["XRB, 2014-SGR-521"],"award-info":[{"award-number":["XRB, 2014-SGR-521"]}],"id":[{"id":"10.13039\/501100002809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"AGAUR \u2013 Ajuts programa Beatriu de Pin\u00f3s (Modalitat B)","award":["2014_BP_B_00075"],"award-info":[{"award-number":["2014_BP_B_00075"]}]},{"name":"MINECO-FEDER","award":["Bio2016-75327-R"],"award-info":[{"award-number":["Bio2016-75327-R"]}]},{"name":"European Union\u2019s Seventh Framework Programme","award":["600404"],"award-info":[{"award-number":["600404"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Tumor metastasis is a complex process in which cells detach from the primary tumor and colonize a distant organ. Metastasis is also the main process responsible for cancer-related death. Despite the enormous efforts made to unravel the metastatic process, there is no effective therapy, and patients with metastatic tumors have poor prognosis. In this regard, there is an urgent need for new therapeutic tools for the treatment of this disease. Small molecules with the capacity to reduce cell migration could be used to treat metastasis. Migrastatin-core analogs are naturally inspired macrocycles that inhibit pathological cell migration and are able to reduce metastasis in animal models. Migrastatin analogs can be synthesized from a common advanced intermediate. Herein we present a review of the synthetic approaches that can be used to prepare this key intermediate, together with a review of the biological activity of migrastatin-core analogs and current hypotheses concerning their mechanism of action.<\/jats:p>","DOI":"10.3390\/molecules22020198","type":"journal-article","created":{"date-parts":[[2017,2,10]],"date-time":"2017-02-10T05:27:09Z","timestamp":1486704429000},"page":"198","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["The Therapeutic Potential of Migrastatin-Core Analogs for the Treatment of Metastatic Cancer"],"prefix":"10.3390","volume":"22","author":[{"given":"Ernest","family":"Giralt","sequence":"first","affiliation":[{"name":"Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, C\/Baldiri Reixac 10, Barcelona E-08028, Spain"},{"name":"Department of Organic Chemistry, University of Barcelona, Marti i Franques 1-11, Barcelona E-08028, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6068-5975","authenticated-orcid":false,"given":"Daniele","family":"Lo Re","sequence":"additional","affiliation":[{"name":"Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, C\/Baldiri Reixac 10, Barcelona E-08028, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2017,2,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"559","DOI":"10.1016\/j.ceb.2005.08.002","article-title":"Cell migration in tumors","volume":"17","author":"Yamaguchi","year":"2005","journal-title":"Curr. Opin. Cell Biol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"593","DOI":"10.2174\/1568026033452348","article-title":"Small-molecule inhibitors of actin dynamics and cell motility","volume":"3","author":"Fenteany","year":"2003","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1130","DOI":"10.7164\/antibiotics.53.1130","article-title":"Migrastatin, a new inhibitor of tumor cell migration from Streptomyces sp. MK929-43F1. Taxonomy, fermentation, isolation and biological activities","volume":"53","author":"Nakae","year":"2000","journal-title":"J. Antibiot."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1228","DOI":"10.7164\/antibiotics.53.1228","article-title":"Migrastatin, a novel 14-membered lactone from Streptomyces sp. MK929-43F1","volume":"53","author":"Nakae","year":"2000","journal-title":"J. Antibiot."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"141","DOI":"10.7164\/antibiotics.55.141","article-title":"Migrastatin and a new compound, isomigrastatin, from Streptomyces platensis","volume":"55","author":"Woo","year":"2002","journal-title":"J. Antibiot."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1038\/ja.2006.62","article-title":"Suppression of Multidrug Resistance by Migrastatin","volume":"59","author":"Takemoto","year":"2006","journal-title":"J. Antibiot."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"685","DOI":"10.1038\/ja.2006.91","article-title":"Migrastatin Acts as a Muscarinic Acetylcholine Receptor Antagonist","volume":"59","author":"Nakae","year":"2006","journal-title":"J. Antibiot."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"6042","DOI":"10.1021\/ja0349103","article-title":"The Total Synthesis of (+)-Migrastatin","volume":"125","author":"Gaul","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"11326","DOI":"10.1021\/ja048779q","article-title":"The Migrastatin Family: Discovery of Potent Cell Migration Inhibitors by Chemical Synthesis","volume":"126","author":"Gaul","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"4800","DOI":"10.1002\/ejoc.200600760","article-title":"Total Synthesis of (+)-Migrastatin","volume":"2006","author":"Reymond","year":"2006","journal-title":"Eur. J. Org. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"6083","DOI":"10.1016\/j.tetlet.2006.06.082","article-title":"A convergent synthesis of the macrolide core of migrastatin","volume":"47","author":"Das","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"6748","DOI":"10.1002\/ejoc.201001097","article-title":"Synthesis of the Macrolactone of Migrastatin and Analogues with Potent Cell-Migration Inhibitory Activity","volume":"2010","author":"Dias","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"4225","DOI":"10.1016\/j.tetlet.2013.05.137","article-title":"Stereoselective formal synthesis of macrolidecore of migrastatin using late stage C\u2013H oxidation","volume":"54","author":"Gade","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1459","DOI":"10.1002\/cbic.201402061","article-title":"Synthesis of migrastatin and its macroketone analogue and in vivo FRAP analysis of the macroketone on E-cadherin dynamics","volume":"15","author":"Zhou","year":"2014","journal-title":"Chembiochem. Eur. J. Chem. Biol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1447","DOI":"10.1016\/j.crci.2008.08.004","article-title":"Migrastatin and analogues: New anti-metastatic agents","volume":"11","author":"Reymond","year":"2008","journal-title":"C. R. Chim."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"9039","DOI":"10.1016\/S0040-4039(02)02281-5","article-title":"Synthesis of the macrolide core of migrastatin","volume":"43","author":"Gaul","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"5918","DOI":"10.1016\/j.tet.2007.02.107","article-title":"Synthesis of migrastatin and its macrolide core","volume":"63","author":"Reymond","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"18109","DOI":"10.1002\/chem.201502861","article-title":"Synthesis of Migrastatin Analogues as Inhibitors of Tumour Cell Migration: Exploring Structural Change in and on the Macrocyclic Ring","volume":"21","author":"LoRe","year":"2015","journal-title":"Chem. A Eur. J."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Majchrzak, K., Lo Re, D., Gajewska, M., Bulkowska, M., Homa, A., Pawlowski, K., Motyl, T., Murphy, P.V., and Krol, M. (2013). Migrastatin analogues inhibit canine mammary cancer cell migration and invasion. PLoS ONE, 8.","DOI":"10.1371\/journal.pone.0076789"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"14381","DOI":"10.1016\/S0040-4020(99)00896-0","article-title":"CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure \u03b2-blockers","volume":"55","author":"Kitaori","year":"1999","journal-title":"Tetrahedron"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1016\/S0040-4020(97)10289-7","article-title":"A cytosine analogue containing a conformationally flexible acyclic linker for triplex formation at sites with contiguous G-C base pairs","volume":"54","author":"Xiang","year":"1998","journal-title":"Tetrahedron"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1256","DOI":"10.1021\/ja00291a027","article-title":"Chelation-controlled facially selective cyclocondensation reactions of chiral alkoxy aldehydes: Syntheses of a mouse androgen and of a carbon-linked disaccharide","volume":"107","author":"Danishefsky","year":"1985","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5848","DOI":"10.1021\/ja00513a075","article-title":"Lanthanoids in organic synthesis. 5. Selective reductions of ketones in the presence of aldehydes","volume":"101","author":"Luche","year":"1979","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Ferrier, R.J. (1964). Unsaturated carbohydrates. Part II. Three reactions leading to unsaturated glycopyranosides. J. Chem. Soc. (Resum.), 5443\u20135449.","DOI":"10.1039\/jr9640005443"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3611","DOI":"10.1021\/ja00479a061","article-title":"Olefin homologation with titanium methylene compounds","volume":"100","author":"Tebbe","year":"1978","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"953","DOI":"10.1021\/ol990909q","article-title":"Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands","volume":"1","author":"Scholl","year":"1999","journal-title":"Organ. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"4630","DOI":"10.1021\/jo0101297","article-title":"Efficient Synthesis of Enantiopure Conduritols by Ring-Closing Metathesis","volume":"66","author":"Iversen","year":"2001","journal-title":"J. Organ. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4473","DOI":"10.1016\/S0957-4166(99)00517-0","article-title":"A new and concise synthetic route to an enantiopure (+)-conduritol-E derivative from diethyl l-tartrate","volume":"10","author":"Lee","year":"1999","journal-title":"Tetrahedron Asymm."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1038","DOI":"10.1021\/ja039714a","article-title":"Discovery of Potent Cell Migration Inhibitors through Total Synthesis: Lessons from Structure\u2013Activity Studies of (+)-Migrastatin","volume":"126","author":"Njardarson","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2600","DOI":"10.1021\/jo0162639","article-title":"Synthesis of New Trans Double-Bond Sphingolipid Analogues: \u03944,6 and \u03946 Ceramides","volume":"67","author":"Chun","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"7889","DOI":"10.1021\/jo00104a054","article-title":"Effects of Olefin Geometry on the Stereochemistry of Lewis Acid Mediated Additions of Crotylstannanes to Aldehydes","volume":"59","author":"Keck","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4405","DOI":"10.1016\/S0040-4039(00)85909-2","article-title":"Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination","volume":"24","author":"Still","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2391","DOI":"10.1080\/00397919108021600","article-title":"A Convenient Method for the Synthesis of bis-Trifluoroethyl Phosphonoacetates","volume":"21","author":"Patois","year":"1991","journal-title":"Synth. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"9434","DOI":"10.1021\/ja00050a024","article-title":"Total synthesis of (+)-calyculin A","volume":"114","author":"Evans","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"8747","DOI":"10.1016\/S0040-4020(00)00804-8","article-title":"Asymmetric Epoxide Cyclisation Route to the F-pyran Fragment of the Altohyrtins and Key Aldol Studies","volume":"56","author":"Anderson","year":"2000","journal-title":"Tetrahedron"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3217","DOI":"10.1021\/ol0400342","article-title":"Improved Procedure for the Oxidative Cleavage of Olefins by OsO4\u2013NaIO4","volume":"6","author":"Yu","year":"2004","journal-title":"Org. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"652","DOI":"10.1055\/s-1996-4254","article-title":"A Synthesis of (+)-Herboxidiene A","volume":"1996","author":"Smith","year":"1996","journal-title":"Synthesis"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7277","DOI":"10.1021\/ja00019a027","article-title":"A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species","volume":"113","author":"Dess","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4745","DOI":"10.1021\/jo000068x","article-title":"Z-Selective Horner\u2013Wadsworth\u2013Emmons Reaction of Ethyl (Diarylphosphono)acetates Using Sodium Iodide and DBU","volume":"65","author":"Ando","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2127","DOI":"10.1021\/ja00398a058","article-title":"Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates","volume":"103","author":"Evans","year":"1981","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4675","DOI":"10.1016\/0040-4039(80)88091-9","article-title":"Enantioselective aldol condensations via boron enolates. A steric model for asymmetric induction","volume":"21","author":"Evans","year":"1980","journal-title":"Tetrahedron Lett."},{"key":"ref_42","first-page":"1371","article-title":"An Improved Procedure for Asymmetric Aldol Additions with N-Acyl Oxazolidinones, Oxazolidinethiones and Thiazolidinethiones","volume":"2004","author":"Crimmins","year":"2004","journal-title":"Synlett"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"894","DOI":"10.1021\/jo001387r","article-title":"Asymmetric Aldol Additions: Use of Titanium Tetrachloride and (\u2212)-Sparteine for the Soft Enolization of N-Acyl Oxazolidinones, Oxazolidinethiones, and Thiazolidinethiones","volume":"66","author":"Crimmins","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/S0040-4039(01)02104-9","article-title":"Synthesis of C13-C22 fragment of the marine sponge polyketide callystatin A","volume":"43","author":"Dias","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1021\/ol027211o","article-title":"Total Synthesis of (\u2212)-Pironetin","volume":"5","author":"Dias","year":"2003","journal-title":"Org. Lett."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2225","DOI":"10.1021\/jo047732k","article-title":"Total Synthesis of (+)-Crocacin D","volume":"70","author":"Dias","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"3951","DOI":"10.1021\/ol016845c","article-title":"Total Synthesis of (+)-Crocacin C","volume":"3","author":"Dias","year":"2001","journal-title":"Org. Lett."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2587","DOI":"10.1021\/ol0491078","article-title":"Short Synthesis of the 6,6-Spiroketal Cores of Spirofungins A and B","volume":"6","author":"Dias","year":"2004","journal-title":"Org. Lett."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1016\/j.tetlet.2005.10.151","article-title":"A short approach to trisubstituted \u03b3-butyrolactones","volume":"47","author":"Dias","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3448","DOI":"10.1021\/ja00117a014","article-title":"Total Synthesis of the Polyether Antibiotic Lonomycin A (Emericid)","volume":"117","author":"Evans","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1055\/s-1994-25538","article-title":"Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis","volume":"1994","author":"Ley","year":"1994","journal-title":"Synthesis"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"6392","DOI":"10.1021\/ja00173a035","article-title":"Titanium-mediated carbonyl olefinations. 1. Methylenations of carbonyl compounds with dimethyltitanocene","volume":"112","author":"Petasis","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4105","DOI":"10.1016\/0040-4039(95)00726-S","article-title":"Practical synthesis of Z-unsaturated esters by using a new Horner-Emmons reagent, ethyl diphenylphosphonoacetate","volume":"36","author":"Ando","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1934","DOI":"10.1021\/jo970057c","article-title":"Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner\u2013Emmons Reagents, Ethyl (Diarylphosphono)acetates","volume":"62","author":"Ando","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"7159","DOI":"10.1016\/S0040-4039(01)01502-7","article-title":"Allyltrichlorostannane additions to chiral dipeptide aldehydes","volume":"42","author":"Dias","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1845","DOI":"10.1055\/s-2002-34891","article-title":"Short Total Synthesis of Aspartyl Protease Inhibitors L-685,434, L-682,679 and L-685,458","volume":"2002","author":"Dias","year":"2002","journal-title":"Synlett"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"0603","DOI":"10.1055\/s-2003-37649","article-title":"Allyltrichlorostannane Additions to \u03b1-Amino Aldehydes: Application to the Total Synthesis of the Aspartyl Protease Inhibitors L-682,679, L-684,414, L-685,434, and L-685,458","volume":"2003","author":"Dias","year":"2003","journal-title":"Synthesis"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"949","DOI":"10.1021\/ol015652m","article-title":"An Aldol Approach to the Synthesis of the EF Fragment of Spongistatin 1","volume":"3","author":"Crimmins","year":"2001","journal-title":"Org. Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"8411","DOI":"10.1021\/jo981337a","article-title":"Z-Selective Horner\u2013Wadsworth\u2013Emmons Reaction of \u03b1-Substituted Ethyl (Diarylphosphono)acetates with Aldehydes1","volume":"63","author":"Ando","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"6970","DOI":"10.1021\/ja0500198","article-title":"Serial Ligand Catalysis: A Highly Selective Allylic C\u2212H Oxidation","volume":"127","author":"Chen","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"12584","DOI":"10.1021\/ja206013j","article-title":"Synthetic Versatility in C\u2013H Oxidation: A Rapid Approach to Differentiated Diols and Pyrans from Simple Olefins","volume":"133","author":"Gormisky","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"9032","DOI":"10.1021\/ja063096r","article-title":"Macrolactonization via Hydrocarbon Oxidation","volume":"128","author":"Fraunhoffer","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1038\/nchem.351","article-title":"Total synthesis and study of 6-deoxyerythronolide B by late-stage C-H oxidation","volume":"1","author":"Stang","year":"2009","journal-title":"Nat. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2094","DOI":"10.1002\/anie.201007309","article-title":"On the Macrocyclization of the Erythromycin Core: Preorganization is Not Required","volume":"50","author":"Stang","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1535","DOI":"10.1021\/ja00213a029","article-title":"Chiral synthesis via organoboranes. 13. A highly diastereoselective and enantioselective addition of [(Z)-.gamma.-alkoxyallyl]diisopinocampheylboranes to aldehydes","volume":"110","author":"Brown","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"7648","DOI":"10.1002\/chem.200800623","article-title":"Dinuclear Zinc-Catalyzed Asymmetric Desymmetrization of Acyclic 2-Substituted-1,3-Propanediols: A Powerful Entry into Chiral Building Blocks","volume":"14","author":"Trost","year":"2008","journal-title":"Chem. A Eur. J."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1002\/anie.200604053","article-title":"Total Synthesis of Rapamycin","volume":"46","author":"Maddess","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/jo971176v","article-title":"NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities","volume":"62","author":"Gottlieb","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"6684","DOI":"10.1016\/j.tetlet.2009.09.080","article-title":"A simple method for the conversion of carboxylic acids into thioacids with Lawesson\u2019s reagent","volume":"50","author":"Rao","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1016\/j.cccn.2005.02.023","article-title":"Glucuronidation in therapeutic drug monitoring","volume":"358","author":"Shipkova","year":"2005","journal-title":"Clin. Chim. Acta Int. J. Clin. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1002\/med.20035","article-title":"Morphine-6-glucuronide: Actions and mechanisms","volume":"25","author":"Kilpatrick","year":"2005","journal-title":"Med. Res. Rev."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1748","DOI":"10.1038\/sj.bjp.0703235","article-title":"Comparison of the activity and disposition of the novel cholesterol absorption inhibitor, SCH58235, and its glucuronide, SCH60663","volume":"129","author":"Farley","year":"2000","journal-title":"Br. J. Pharmacol."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1039\/c3np70003h","article-title":"Glucuronides from metabolites to medicines: A survey of the in vivo generation, chemical synthesis and properties of glucuronides","volume":"30","author":"Stachulski","year":"2013","journal-title":"Nat. Prod. Rep."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"9628","DOI":"10.1021\/jo0612675","article-title":"Protecting Groups for Glucuronic Acid: Application to the Synthesis of New Paclitaxel (Taxol) Derivatives","volume":"71","author":"Schmidt","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"3074","DOI":"10.1002\/anie.200604909","article-title":"Highly Efficient and Versatile Synthesis of Proteoglycan Core Structures from 1,6-Anhydro-\u03b2-lactose as a Key Starting Material","volume":"46","author":"Shimawaki","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"6747","DOI":"10.1021\/jo101090f","article-title":"SnCl4- and TiCl4-Catalyzed Anomerization of Acylated O- and S-Glycosides: Analysis of Factors That Lead to Higher \u03b1:\u03b2 Anomer Ratios and Reaction Rates","volume":"75","author":"Pilgrim","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"902","DOI":"10.1002\/chem.200601111","article-title":"Glycosidation\u2013Anomerisation Reactions of 6,1-Anhydroglucopyranuronic Acid and Anomerisation of \u03b2-d-Glucopyranosiduronic Acids Promoted by SnCl4","volume":"13","author":"Pitt","year":"2007","journal-title":"Chem. A Eur. J."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"939","DOI":"10.1021\/ol802915h","article-title":"\u03b1-Glycosphingolipids via Chelation-Induced Anomerization of O- and S-Glucuronic and Galacturonic Acid Derivatives","volume":"11","author":"Pilgrim","year":"2009","journal-title":"Org. Lett."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"5168","DOI":"10.1021\/ol202042h","article-title":"Synthesis of \u03b1-S-Glycosphingolipids Based on Uronic Acids","volume":"13","author":"Murphy","year":"2011","journal-title":"Org. Lett."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"14836","DOI":"10.1002\/chem.201302572","article-title":"Regiospecific Anomerisation of Acylated Glycosyl Azides and Benzoylated Disaccharides by Using TiCl4","volume":"19","author":"Farrell","year":"2013","journal-title":"Chem. A Eur. J."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1021\/acs.orglett.5b03591","article-title":"Lewis Acid Induced Anomerization of Se-Glycosides. Application to Synthesis of \u03b1-Se-GalCer","volume":"18","author":"McDonagh","year":"2016","journal-title":"Org. Lett."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"3191","DOI":"10.1016\/j.tet.2014.03.029","article-title":"Synthesis of \u03b1-galactosyl ceramide analogues with an \u03b1-triazole at the anomeric carbon","volume":"70","author":"McDonagh","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"1104","DOI":"10.7164\/antibiotics.54.1104","article-title":"Migrastatin, a novel 14-membered ring macrolide, inhibits anchorage-independent growth of human small cell lung carcinoma Ms-1 cells","volume":"54","author":"Takemoto","year":"2001","journal-title":"J. Antibiot."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1238","DOI":"10.1111\/j.1349-7006.1988.tb01550.x","article-title":"Vincristine-resistant human cancer KB cell line and increased expression of multidrug-resistance gene","volume":"79","author":"Kohno","year":"1988","journal-title":"Jpn. J. Cancer Res."},{"key":"ref_85","first-page":"1967","article-title":"Overcoming of vincristine resistance in P388 leukemia in vivo and in vitro through enhanced cytotoxicity of vincristine and vinblastine by verapamil","volume":"41","author":"Tsuruo","year":"1981","journal-title":"Cancer Res."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"3772","DOI":"10.1073\/pnas.0500658102","article-title":"Synthetic analogues of migrastatin that inhibit mammary tumor metastasis in mice","volume":"102","author":"Shan","year":"2005","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"3224","DOI":"10.1021\/ja9101503","article-title":"Diverted Total Synthesis Leads to the Generation of Promising Cell-Migration Inhibitors for Treatment of Tumor Metastasis: In vivo and Mechanistic Studies on the Migrastatin Core Ether Analog","volume":"132","author":"Oskarsson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"15074","DOI":"10.1073\/pnas.1015247108","article-title":"Emergence of potent inhibitors of metastasis in lung cancer via syntheses based on migrastatin","volume":"108","author":"Lecomte","year":"2011","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_89","first-page":"1486","article-title":"Reduction of Established Spontaneous Mammary Carcinoma Metastases following Immunotherapy with Major Histocompatibility Complex Class II and B7.1 Cell-based Tumor Vaccines","volume":"58","author":"Pulaski","year":"1998","journal-title":"Cancer Res."},{"key":"ref_90","first-page":"1399","article-title":"Selective Events in the Metastatic Process Defined by Analysis of the Sequential Dissemination of Subpopulations of a Mouse Mammary Tumor","volume":"52","author":"Aslakson","year":"1992","journal-title":"Cancer Res."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"518","DOI":"10.1038\/nature03799","article-title":"Genes that mediate breast cancer metastasis to lung","volume":"436","author":"Minn","year":"2005","journal-title":"Nature"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1172\/JCI22320","article-title":"Distinct organ-specific metastatic potential of individual breast cancer cells and primary tumors","volume":"115","author":"Minn","year":"2005","journal-title":"J. Clin. Investig."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"1062","DOI":"10.1038\/nature08978","article-title":"Migrastatin analogues target fascin to block tumour metastasis","volume":"464","author":"Chen","year":"2010","journal-title":"Nature"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"186","DOI":"10.1158\/1078-0432.186.11.1","article-title":"The expression of fascin, an actin-bundling motility protein, correlates with hormone receptor-negative breast cancer and a more aggressive clinical course","volume":"11","author":"Yoder","year":"2005","journal-title":"Clin. Cancer Res."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"870","DOI":"10.1054\/bjoc.2000.1395","article-title":"Fascin, an actin-bundling protein associated with cell motility, is upregulated in hormone receptor negative breast cancer","volume":"83","author":"Grothey","year":"2000","journal-title":"Br. J. Cancer"},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"4591","DOI":"10.1091\/mbc.e07-02-0157","article-title":"Dual Actin-bundling and Protein Kinase C-binding Activities of Fascin Regulate Carcinoma Cell Migration Downstream of Rac and Contribute to Metastasis","volume":"18","author":"Hashimoto","year":"2007","journal-title":"Mol. Biol. Cell"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"6844","DOI":"10.1158\/0008-5472.CAN-07-0929","article-title":"Fascin, a novel target of beta-catenin-TCF signaling, is expressed at the invasive front of human colon cancer","volume":"67","author":"Vignjevic","year":"2007","journal-title":"Cancer Res."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"5087","DOI":"10.1016\/S0021-9258(18)89183-9","article-title":"Purification and characterization of an F-actin-bundling 55-kilodalton protein from HeLa cells","volume":"260","author":"Matsumura","year":"1985","journal-title":"J. Biol. Chem."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"3873","DOI":"10.1016\/j.tetlet.2010.05.056","article-title":"Confirmation of the Structures of Synthetic Derivatives of Migrastatin in the Light of Recently Disclosed Crystallographically Based Claims","volume":"51","author":"Nagorny","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1007\/BF03195709","article-title":"Transcriptomic signature of cell lines isolated from canine mammary adenocarcinoma metastases to lungs","volume":"51","author":"Krol","year":"2010","journal-title":"J. Appl. Genet."},{"key":"ref_101","doi-asserted-by":"crossref","unstructured":"Majchrzak, K., Paw\u0142owski, K.M., Orzechowska, E.J., Dolka, I., Mucha, J., Motyl, T., and Kr\u00f3l, M. (2012). A role of ghrelin in canine mammary carcinoma cells proliferation, apoptosis and migration. BMC Vet. Res., 8.","DOI":"10.1186\/1746-6148-8-170"},{"key":"ref_102","doi-asserted-by":"crossref","unstructured":"Kr\u00f3l, M., Paw\u0142owski, K.M., Majchrzak, K., Gajewska, M., Majewska, A., and Motyl, T. (2012). Global gene expression profiles of canine macrophages and canine mam mary cancer cells grown as a co-culture in vitro. BMC Vet. Res., 8.","DOI":"10.1186\/1746-6148-8-16"},{"key":"ref_103","doi-asserted-by":"crossref","unstructured":"Manuali, E., De Giuseppe, A., Feliziani, F., Forti, K., Casciari, C., Marchesi, M.C., Pacifico, E., Paw\u0142owski, K.M., Majchrzak, K., and Kr\u00f3l, M. (2012). CA 15\u20133 cell lines and tissue expression in canine mammary cancer and the correlation between serum levels and tumour histological grade. BMC Vet. Res., 8.","DOI":"10.1186\/1746-6148-8-86"},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"863","DOI":"10.1083\/jcb.200603013","article-title":"Role of fascin in filopodial protrusion","volume":"174","author":"Vignjevic","year":"2006","journal-title":"J. Cell Biol."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"446","DOI":"10.1038\/nrm2406","article-title":"Filopodia: Molecular architecture and cellular functions","volume":"9","author":"Mattila","year":"2008","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1016\/j.cell.2004.07.019","article-title":"Lamellipodial versus filopodial mode of the actin nanomachinery: Pivotal role of the filament barbed end","volume":"118","author":"Mejillano","year":"2004","journal-title":"Cell"},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"871","DOI":"10.1016\/j.cell.2009.11.007","article-title":"Epithelial-Mesenchymal Transitions in Development and Disease","volume":"139","author":"Thiery","year":"2009","journal-title":"Cell"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"1787","DOI":"10.1038\/emboj.2010.92","article-title":"Snail1 links transcriptional control with epigenetic regulation","volume":"29","author":"Christofori","year":"2010","journal-title":"EMBO J."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"2917","DOI":"10.1158\/0008-5472.CAN-11-3498","article-title":"Dishonorable Discharge: The Oncogenic Roles of Cleaved E-Cadherin Fragments","volume":"72","author":"David","year":"2012","journal-title":"Cancer Res."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"a003129","DOI":"10.1101\/cshperspect.a003129","article-title":"Involvement of Members of the Cadherin Superfamily in Cancer","volume":"1","author":"Berx","year":"2009","journal-title":"Cold Spring Harb. Perspect. Biol."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/0304-419X(94)90003-5","article-title":"Cadherin expression in carcinomas: Role in the formation of cell junctions and the prevention of invasiveness","volume":"1198","author":"Birchmeier","year":"1994","journal-title":"Biochim. Biophys. Acta (BBA) Rev. Cancer"},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1038\/ng0594-98","article-title":"Mutations of the E-cadherin gene in human gynecologic cancers","volume":"7","author":"Risinger","year":"1994","journal-title":"Nat. Genet."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"6107","DOI":"10.1002\/j.1460-2075.1995.tb00301.x","article-title":"E-cadherin is a tumour\/invasion suppressor gene mutated in human lobular breast cancers","volume":"14","author":"Berx","year":"1995","journal-title":"EMBO J."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"2316","DOI":"10.1073\/pnas.96.5.2316","article-title":"Mutated epithelial cadherin is associated with increased tumorigenicity and loss of adhesion and of responsiveness to the motogenic trefoil factor 2 in colon carcinoma cells","volume":"96","author":"Efstathiou","year":"1999","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1073\/pnas.0908428107","article-title":"Mutant p53 drives metastasis and overcomes growth arrest\/senescence in pancreatic cancer","volume":"107","author":"Morton","year":"2010","journal-title":"Proc. Natl. Acad. Sci. USA"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/2\/198\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:27:50Z","timestamp":1760207270000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/2\/198"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,2,9]]},"references-count":115,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2017,2]]}},"alternative-id":["molecules22020198"],"URL":"https:\/\/doi.org\/10.3390\/molecules22020198","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2017,2,9]]}}}