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Asymmetric Synthesis and Binding Study of New Longâ Chain HPAâ 12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT

dc.contributor.authorĎuriš, Andrej
dc.contributor.authorDaïch, Adam
dc.contributor.authorSantos, Cécile
dc.contributor.authorFleury, Laurence
dc.contributor.authorAusseil, Frédéric
dc.contributor.authorRodriguez, Frédéric
dc.contributor.authorBallereau, Stéphanie
dc.contributor.authorGénisson, Yves
dc.contributor.authorBerkeš, Dušan
dc.date.accessioned2017-06-16T20:17:00Z
dc.date.available2017-06-16T20:17:00Z
dc.date.issued2016-05-04
dc.identifier.citationĎuriš, Andrej ; Daïch, Adam ; Santos, Cécile ; Fleury, Laurence; Ausseil, Frédéric ; Rodriguez, Frédéric ; Ballereau, Stéphanie ; Génisson, Yves ; Berkeš, Dušan (2016). "Asymmetric Synthesis and Binding Study of New Longâ Chain HPAâ 12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT." Chemistry â A European Journal 22(19): 6676-6686.
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttps://hdl.handle.net/2027.42/137621
dc.description.abstractA series of 12 analogues of the Cer transfer protein (CERT) antagonist HPAâ 12 with long aliphatic chains were prepared as their (1R,3S)â syn and (1R,3R)â anti stereoisomers from pivotal chiral oxoamino acids. The enantioselective access to these intermediates as well as their ensuing transformation relied on a practical crystallizationâ induced asymmetric transformation (CIAT) process. Sonogashira coupling followed by triple bond reduction and thiophene ring hydrodesulfurization (HDS) into the corresponding alkane moieties was then implemented to complete the synthetic routes delivering the targeted HPAâ 12 analogues in concise 4â to 6â step reaction sequences. Ten compounds were evaluated regarding their ability to bind to the CERT START domain by using the recently developed timeâ resolved FRETâ based homogeneous (HTRâ FRET) binding assay. The introduction of a lipophilic appendage on the phenyl moiety led to an overall 10â to 1000â fold enhancement of the protein binding, with the highest effect being observed for a nâ hexyl residue in the meta position. The importance of the phenyl ring for the activity was indicated by the reduced potency of the 3â deoxyphytoceramide aliphatic analogues. The 1,3â syn stereoisomers were systematically more potent than their 1,3â anti analogues. In silico studies were used to rationalized these trends, leading to a model of protein recognition coherent with the stronger binding of (1R,3S)â syn HPAs.Analogues of the Cer transfer protein (CERT) antagonist HPAâ 12 were prepared as their (1R,3S)â syn and (1R,3R)â anti stereoisomers from pivotal enantiopure oxoamino acids in 4â 6 steps. The sequence relied on a practical crystallizationâ induced asymmetric transformation (CIAT) process followed by Sonogashira coupling and triple bond reduction in tandem or not and hydrodesulfurization of the thiophene ring into corresponding alkane moieties (see scheme).
dc.publisherWiley Periodicals, Inc.
dc.subject.otheracylation
dc.subject.otherantitumor agents
dc.subject.otherenantioselectivity
dc.subject.othersphingolipids
dc.subject.othersynthetic methods
dc.titleAsymmetric Synthesis and Binding Study of New Longâ Chain HPAâ 12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137621/1/chem201505121.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/137621/2/chem201505121-sup-0001-misc_information.pdf
dc.identifier.doi10.1002/chem.201505121
dc.identifier.sourceChemistry â A European Journal
dc.identifier.citedreferenceI. Vanâ Overmeire, S. A. Boldin, K. Venkataraman, R. Zisling, S. Deâ Jonghe, S. Vanâ Calenbergh, D. Deâ Keukeleire, A. H. Futerman, P. Herdewijn, J. Med. Chem. 2000, 43, 4189 â 4199;
dc.identifier.citedreference 
dc.identifier.citedreferenceA. Singh, H.-J. Ha, J. Park, J. H. Kim, W. K. Lee, Bioorg. Med. Chem. 2011, 19, 6174 â 6181;
dc.identifier.citedreferenceH.-J. Ha, M. Ch. Hong, S. W. Ko, Y. W. Kim, W. K. Leeb, J. Park, Bioorg. Med. Chem. Lett. 2006, 16, 1880 â 1883.
dc.identifier.citedreferenceA. W. McDonagh, P. V. Murphy, Tetrahedron 2014, 70, 3191 â 3196.
dc.identifier.citedreferenceU. Hillaert, S. Boldin-Adamsky, J. Rozenski, R. Busson, A. H. Futerman, S. Vanâ Calenbergh, Bioorg. Med. Chem. 2006, 14, 5273 â 5284 and references therein.
dc.identifier.citedreferenceM. Moreno, C. Murruzzu, A. Riera, Bioorg. Med. Chem. 2011, 19, 5184 â 5187 and references therein.
dc.identifier.citedreference 
dc.identifier.citedreferenceY. Salma, S. Ballereau, C. Maaliki, S. Ladeira, N. Andrieu-Abadie, Y. Génisson, Org. Biomol. Chem. 2010, 8, 3227 â 3243;
dc.identifier.citedreferenceY. Salma, S. Ballereau, S. Ladeira, C. Lepetit, R. Chauvin, N. Andrieu-Abadie, Y. Génisson, Tetrahedron 2011, 67, 4253 â 4262.
dc.identifier.citedreference 
dc.identifier.citedreferenceS. D. Karyakarte, T. P. Smith, S. R. Chemler, J. Org. Chem. 2012, 77, 7755 â 7760;
dc.identifier.citedreferenceR. Ramanujam, S. Ganjihal, N. Kalyanam, M. Majeed, Tetrahedron: Asymmetry 2013, 24, 663 â 668.
dc.identifier.citedreferenceFor recent review in this field, see: J. Rentner, M. Kljajic, L. Offner, R. Breinbauer, Tetrahedron 2014, 70, 8983.
dc.identifier.citedreferenceFor representative examples using this protocol see:
dc.identifier.citedreferenceS. Michelliza, A. Al-Mourabit, A. Gateau-Olesker, C. Marazano, J. Org. Chem. 2002, 67, 6474 â 6478;
dc.identifier.citedreferenceY. L. Gol’Dfarb, B. P. Fabrichnyi, I. F. Shalavina, Tetrahedron 1961, 17, 21 â 36. For stereoselective reduction of 2,3-disubstituted and 2,3,4,5-tetrasubstituted thiophenes, see:
dc.identifier.citedreferenceP. A. Jacobi, M. Egberston, R. F. Frechette, S. Miao, C. K. K. T. Weiss, Tetrahedron 1988, 44, 3327 â 3338;
dc.identifier.citedreferenceP. A. Jacobi, R. F. Frechette, Tetrahedron Lett. 1987, 28, 2937 â 2940.
dc.identifier.citedreferenceP. Radhaâ Krishna, B. Lavanya, A. Ilangovan, G. V. M. Sharma, Tetrahedron: Asymmetry 2000, 11, 4463 â 4472.
dc.identifier.citedreference 
dc.identifier.citedreferenceP. Å afaÅ , J. Žužiova, M. BoboÅ¡iková, Å . Marchalín, N. Pronayová, S. Comesse, A. Daïch, Tetrahedron: Asymmetry 2009, 20, 2137 â 2144;
dc.identifier.citedreferenceP. Å afaÅ , J. Žužiova, Å . Marchalín, E. Tothova, N. Pronayová, L. Å vorc, V. Vrabel, A. Daïch, Tetrahedron: Asymmetry 2009, 20, 626 â 634;
dc.identifier.citedreferenceÅ . Marchalín, J. Žužiova, K. KadleÄ ikova, P. Å afaÅ , P. Baran, V. Dalla, A. Daïch, Tetrahedron Lett. 2007, 48, 697 â 702.
dc.identifier.citedreferenceD. J. Baek, J.-H. Seo, C. Lim, J. H. Kim, D. H. Chung, W.-J. Cho, C.-Y. Kang, S. Kim, ACS Med. Chem. Lett. 2011, 2, 544 â 548.
dc.identifier.citedreferenceS. Combemale, C. Santos, F. Rodriguez, V. Garcia, C. Galaup, C. Frongia, V. Lobjois, T. Levade, C. Baudoin-Dehoux, S. Ballereau, Y. Genisson, RSC Adv. 2013, 3, 18970 â 18984.
dc.identifier.citedreferenceFor dihydrosphingosine derivatives, see: G. Fabrias, J. Muñoz-Olaya, F. Cingolani, P. Signorelli, J. Casas, V. Gagliostro, R. Ghidoni, Prog. Lipid Res. 2012, 51, 82 â 94. For 6-hydroxysphinganine-based ceramide, see: A. KovÃ¡Ä ik, J. Roh, K. Vávrová, ChemBioChem 2014, 15, 1555 â 1562.
dc.identifier.citedreferenceS. A. F. Morad, M. C. Cabot, Nat. Rev. Cancer 2012, 13, 51 â 65.
dc.identifier.citedreferenceY. A. Hannun, L. M. Obeid, Nat. Rev. Mol. Cell Biol. 2008, 9, 139 â 150.
dc.identifier.citedreferenceT. Yamaji, K. Hanada, Traffic 2015, 16, 101 â 122.
dc.identifier.citedreferenceB. J. Clark, J. Endocrinol. 2012, 212, 257 â 275.
dc.identifier.citedreferenceK. Hanada, Proc. Jpn. Acad. Ser. B 2010, 86, 426 â 437.
dc.identifier.citedreferenceK. Kumagai, S. Yasuda, K. Okemoto, M. Nishijima, S. Kobayashi, K. Hanada, Biochemistry 2005, 280, 6488 â 6495.
dc.identifier.citedreferenceC. Swanton, M. Marani, O. Pardo, P. H. Warne, G. Kelly, E. Sahai, F. Elustondo, J. Chang, J. Temple, A. A. Ahmed, J. D. Brenton, J. Downward, B. Nicke, Cancer cell 2007, 11, 498 â 512.
dc.identifier.citedreferenceA. J. X. Lee, R. Roylance, J. Sander, P. Gorman, D. Endesfelder, M. Kschischo, N. P. Jones, P. East, B. Nicke, S. Spassieva, L. M. Obeid, N. J. Birkbak, Z. Szallasi, N. C. McKnight, A. J. Rowan, V. Speirs, A. M. Hanby, J. Downward, S. A. Tooze, C. Swanton, J. Pathol. 2012, 226, 482 â 494.
dc.identifier.citedreferenceC. Mencarelli, G. H. Bode, M. Losen, M. Kulharia, P. C. Molenaar, R. Veerhuis, H. W. M. Steinbusch, M. H. Deâ Baets, G. A. F. Nicolaes, P. Martinez-Martinez, J. Biol. Chem. 2012, 287, 14897 â 14911.
dc.identifier.citedreferenceH. Aizaki, K. Morikawa, M. Fukasawa, H. Hara, Y. Inoue, H. Tani, K. Saito, M. Nishijima, K. Hanada, Y. Matsuura, M. A. C. Lai, T. Miyamura, T. Wakita, T. Suzuki, J. Virol. 2008, 82, 5715 â 5724.
dc.identifier.citedreferenceY. Amako, G. H. Syed, A. Siddiqui, J. Biol. Chem. 2011, 286, 11265 â 11274.
dc.identifier.citedreferenceI. Derré, R. Swiss, H. Agaisse, PLoS Pathog. 2011, 7, e 1002092 â e 1002092.
dc.identifier.citedreferenceC. A. Elwell, S. Jiang, J. H. Kim, A. Lee, T. Wittmann, K. Hanada, P. Melancon, J. N. Engel, PLoS Pathog. 2011, 7, e 1002198 â e 1002198.
dc.identifier.citedreferenceM. Ueno, H. Kitagawa, H. Ishitani, S. Yasuda, K. Hanada, S. Kobayashi, Tetrahedron Lett. 2001, 42, 7863 â 7865.
dc.identifier.citedreferenceS. Yasuda, H. Kitagawa, M. Ueno, H. Ishitani, M. Fukasawa, M. Nishijima, S. Kobayashi, K. Hanada, J. Biol. Chem. 2001, 276, 43994 â 44002.
dc.identifier.citedreferenceK. Hanada, K. Kumagai, S. Yasuda, Y. Miura, M. Kawano, M. Fukasawa, M. Nishijima, Nature 2003, 426, 803 â 809.
dc.identifier.citedreferenceY. Nakamura, R. Matsubara, H. Kitagawa, S. Kobayashi, K. Kumagai, S. Yasuda, K. Hanada, J. Med. Chem. 2003, 46, 3688 â 3695.
dc.identifier.citedreferenceN. Kudo, K. Kumagai, R. Matsubara, S. Kobayashi, K. Hanada, S. Wakatsuki, R. Kato, J. Mol. Biol. 2010, 396, 245 â 251.
dc.identifier.citedreferenceA. Ä uriÅ¡, T. S. Wiesenganger, D. MoravÄ Ã­ková, P. Baran, J. Kožíšek, A. Daïch, D. BerkeÅ¡, Org. Lett. 2011, 13, 1642 â 1645.
dc.identifier.citedreferenceS. Yasuda, H. Kitagawa, M. Ueno, H. Ishitani, M. Fukasawa, M. Nishijima, S. Kobayashi, K. Hanada, J. Biol. Chem. 2013, 288, 24162.
dc.identifier.citedreference 
dc.identifier.citedreferenceS. Kobayashi, R. Matsubara, Y. Nakamura, H. Kitagawa, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 2507 â 2515;
dc.identifier.citedreferenceS. Kobayashi, R. Matsubara, H. Kitagawa, Org. Lett. 2002, 4, 143 â 145.
dc.identifier.citedreferenceS. Raghavan, A. Rajender, Tetrahedron 2004, 60, 5059 â 5067.
dc.identifier.citedreference 
dc.identifier.citedreferenceJ. R. Snider, J. T. Entrekin, T. S. Snowden, D. Dolliver, Synthesis 2013, 45, 1899 â 1903;
dc.identifier.citedreferenceE. M. Saied, S. Diederich, C. Arenz, Chem. Asian J. 2014, 9, 2092 â 2094;
dc.identifier.citedreferenceJ.-L. Abad, I. Armero, A. Delgado, Tetrahedron Lett. 2015, 56, 1706 â 1708;
dc.identifier.citedreferenceS. Chacko, M. Kalita, R. Ramapanicker, Tetrahedron: Asymmetry 2015, 26, 623 â 631.
dc.identifier.citedreference 
dc.identifier.citedreferenceC. Z. Yao, Z. F. Xiao, X. S. Ning, J. Liu, X. W. Zhang, Y. B. Kang, Org. Lett. 2014, 16, 5824 â 5826;
dc.identifier.citedreferenceZ. F. Xiao, C. Z. Yao, Y. B. Kang, Org. Lett. 2014, 16, 6512 â 6514.
dc.identifier.citedreferenceM. Ueno, Y.-Y. Huang, A. Yamano, S. Kobayashi, Org. Lett. 2013, 15, 2869 â 2871.
dc.identifier.citedreferenceC. Santos, L. Fleury, F. Rodriguez, J. Markus, D. BerkeÅ¡, A. Daïch, F. Ausseil, C. Baudoin-Dehoux, S. Ballereau, Y. Génisson, Bioorg. Med. Chem. 2015, 23, 2004 â 2009.
dc.identifier.citedreferenceFRET or SPR-based in vitro assays were reported to quantify the intermembrane Cer transfer or the real-time Cer extraction activities, respectively, yet without application to the evaluation of inhibitors. For the FRET assay, see: J. Tuuf, M. A. Kjellberg, J. G. Molotkovsky, K. Hanada, P. Mattjus, Biochim. Biophys. Acta Biomembr. 2011, 1808, 229 â 235. For the SPR assay, see: T. Sugiki, H. Takahashi, M. Nagasu, K. Hanada, I. Shimada, Anal. Biochem. 2010, 399, 162 â 167.
dc.identifier.citedreferenceC. Santos, F. Rogriguez, V. Garcia, D. Moravcikova, D. BerkeÅ¡, A. Daïch, T. Levade, C. Baudoin-Dehoux, S. Ballereau, Y. Génisson, ChemBioChem 2014, 15, 2522 â 2528.
dc.identifier.citedreferenceL. Fleury, C. Faux, C. Santos, S. Ballereau, Y. Génisson, F. Ausseil, J. Biomol. Screening 2015, 20, 779 â 787.
dc.identifier.citedreferenceK. P. Bhabak, B. Kleuser, A. Huwiler, C. Arenz, Bioorg. Med. Chem. 2013, 21, 874 â 882.
dc.identifier.citedreferenceL. Lee, A. Abe, J. A. Shayman, J. Biol. Chem. 1999, 274, 14662 â 14669.
dc.identifier.citedreferenceJ. A. Shayman, Drugs Future 2010, 35, 613 â 620.
dc.identifier.citedreferenceUnpublished results: See the Supporting Information.
dc.identifier.citedreferenceN. Kudo, K. Kumagai, N. Tomishige, T. Yamaji, S. Wakatsuki, M. Nishijima, K. Hanada, R. Kato, Proc. Natl. Acad. Sci. USA 2008, 105, 488 â 493.
dc.identifier.citedreferenceJ. Chun, L. He, H.-S. Byun, R. Bittman, J. Org. Chem. 2000, 65, 7634 â 7640.
dc.identifier.citedreferenceV. Blot, U. Jacquemard, H.-U. Reissig, B. Kleuser, Synthesis 2009, 5, 759 â 766.
dc.identifier.citedreferenceS. Grijalvo, X. Matabosch, A. Llebaria, A. Delgado, Eur. J. Org. Chem. 2008, 150 â 155.
dc.identifier.citedreference 
dc.identifier.citedreferenceY. Kim, J. Kim, K. Oh, D.-S. Lee, S. B. Park, ACS Med. Chem. Lett. 2012, 3, 151 â 154;
dc.identifier.citedreferenceY. Kim, K. Oh, H. Song, D.-S. Lee, S. B. Park, J. Med. Chem. 2013, 56, 7100 â 7109.
dc.identifier.citedreferenceM. Kiuchi, K. Adachi, T. Kohara, M. Minoguchi, T. Hanano, Y. Aoki, T. Mishina, M. Arita, N. Nakao, M. Ohtsuki, Y. Hoshino, K. Teshima, K. Chiba, S. Sasaki, T. Fujita, J. Med. Chem. 2000, 43, 2946 â 2961.
dc.identifier.citedreference 
dc.identifier.citedreferenceP. Jakubec, P. Petráš, A. Ä uriÅ¡, D. BerkeÅ¡, Tetrahedron: Asymmetry 2010, 21, 69 â 74;
dc.identifier.citedreferenceD. BerkeÅ¡, P. Jakubec, D. Winklerová, F. Považanec, A. Daïch, Org. Biomol. Chem. 2007, 5, 121 â 124;
dc.identifier.citedreferenceP. Jakubec, D. BerkeÅ¡, A. KolaroviÄ , F. Považanec, Synthesis 2006, 23, 4032 â 4040;
dc.identifier.citedreferenceD. BerkeÅ¡, A. KolaroviÄ , R. Manduch, P. Baran, F. Považanec, Tetrahedron: Asymmetry 2005, 16, 1927 â 1934.
dc.identifier.citedreferenceP. Jakubec, D. BerkeÅ¡, R. Å iÅ¡ka, M. Gardianová, F. Považanec, Tetrahedron: Asymmetry 2006, 17, 1629 â 1637.
dc.identifier.citedreferenceD. BerkeÅ¡, A. KolaroviÄ , F. Považanec, Tetrahedron Lett. 2000, 41, 5257 â 5260.
dc.identifier.citedreferenceFor a general review on Songashira coupling reaction, see:
dc.identifier.citedreferenceR. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874 â 922;
dc.identifier.citedreferenceR. Chinchilla, C. Nájera, Chem. Soc. Rev. 2011, 40, 5084 â 5121.
dc.identifier.citedreference 
dc.identifier.citedreferenceG. Triola, G. Fabriàs, J. Casas, A. Llebaria, J. Org. Chem. 2003, 68, 9924 â 9932;
dc.identifier.citedreferenceS. Deâ Jonghe, I. Lamote, K. Venkataraman, S. A. Boldin, U. Hillaert, J. Rozenski, C. Hendrix, R. Busson, D. Deâ Keukeleire, S. Vanâ Calenbergh, A. H. Futerman, P. Herdewijn, J. Org. Chem. 2002, 67, 988 â 996;
dc.identifier.citedreferenceL. He, H.-S. Byun, R. Bittman, J. Org. Chem. 2000, 65, 7627 â 7633.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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