Abstract
The synthesis and properties of members of the calixarene family functionalised with carbohydrates have been extensively investigated for the past 20 years. These calixsugars show great potential for applications in the fields of medicinal chemistry, drug and gene delivery, through their ability to bind to lectins and to inhibit enzymes. In this chapter, the current therapeutic status of calixsugars for a range of diseases is discussed, including in vivo evaluation. Applications in bacterial infections and cancer are covered, in addition to recent developments in their use as carrier molecules and vectors in gene therapy.
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Yousaf, A.; Abd Hamid, S.; Bunnori, N. M., Ishola, A. A. Drug Des. Dev. Ther. 2015, 9, 2831–2838.
Sun, J.; Blaskovich, M. A.; Jain, R. K.; Delarue, F.; Paris, D.; Brem, S.; Wotoczek-Obadia, M.; Lin, Q.; Coppola, D.; Choi, K.; Mullan, M.; Hamilton, A. D.; Sebti, S. M. Cancer Res. 2004, 64, 3586–3592.
Astorgues-Xerri, L.; Riveiro, M. E.; Tijeras-Raballand, A.; Serova, M.; Rabinovich, G. A., Bieche, I.; Vidaud, M.; de Gramont, A.; Martinet, M.; Cvitkovic, E.; Faivre, S.; Raymond, E. Eur. J. Cancer 2014, 50, 2463–2477.
Tsou, L. K.; Dutschman, G. E.; Gullen, E. A.; Telpoukhovskaia, M.; Cheng, Y.-C.; Hamilton, A. D. Bioorg. Med. Chem. Lett. 2010, 20, 2137–2139.
Mourer, M.; Massimba Dibama, H.; Fontanay, S.; Grare, M., Duval, R. E.; Finance, C.; Regnouf-de-Vains, J.-B. Bioorg. Med. Chem. 2009, 17, 5496–5509; Mourer, M.; Massimba Dibama, H.; Constant, P.; Daffé, M.; Regnouf-de-Vains, J.-B. Bioorg. Med. Chem. 2012, 20, 2035–2041.
Bagnacani, V.; Sansone, F.; Donofrio, G.; Baldini, L.; Casnati, A.; Ungaro, R. Org. Lett. 2008, 10, 3953–3956; Bagnacani, V.; Franceschi, V.; Bassi, M.; Lomazzi, M.; Donofrio, G.; Sansone, F.; Casnati, A.; Ungaro, R. Nature Comm. 2013, 4, 1721; Rodik, R. V.; Klymchenko, A. S.; Jain, N.; Miroshnichenko, S. I.; Richert, L.; Kalchenko, V. I.; Mély, Y. Chem. Eur. J. 2011, 17, 5526–5538.
Consoli, G. M. L.; Granata, G.; Fragassi, G.; Grossi, M.; Sallese, M.; Geraci, C. Org. Biomol. Chem. 2015, 13, 3298–3307; Guo, D.-S.; Wang, K.; Wang, Y.-X.; Liu, Y. J. Am. Chem. Soc. 2012, 134, 10244–10250.
Dondoni, A.; Marra, A. Chem. Rev. 2010, 110, 4949–4977; Fulton, D. A.; Stoddart, J. F. Bioconjug. Chem. 2001, 12, 655–672; Sansone, F.; Casnati A. Chem. Soc. Rev. 2013, 42, 4623–4639.
Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Curr. Opin. Chem. Biol. 2000, 4, 696–703; Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321–327; Mammen, M.; Choi S.-K., Whitesides, G. M. Angew. Chem. Int. Ed. 1998, 37, 2754–2794.
Lundquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555–578.
Gouin, S. G. Chem. Eur. J. 2014, 20, 11616–11628; Compain, P.; Bodlenner, A. ChemBioChem 2014, 15, 1239–1251
Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004–2021; Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057–3064.
Büning, H. EMBO Mol Med, 2013, 5, 1–3.
Seow, Y.; Wood, M. J. Mol. Ther. 2009, 17, 767–777; Yin, H.; Kanasty, R. L.; Eltoukhy, A. A.; Vegas, A. J.; Dorkin, J. R.; Anderson, D. G. Nat. Rev. Genet. 2014, 15, 541–555.
Hayashida, O.; Mizuki, K.; Akagi, K.; Matsuo, A.; Kanamori, T.; Nakai, T.; Sando, S.; Aoyama, Y. J. Am. Chem. Soc. 2003, 125, 594–601.
Aoyama, Y. Chem. Eur. J. 2004, 10. 588–593.
Hayashida, O.; Kato, M.; Akagi, K.; Aoyama, Y. J. Am. Chem. Soc. 1999, 121, 11597–11598.
Hayashida, O.; Matso, A.; Aoyama, Y. Chem. Lett. 2001, 272–273.
Aoyama, Y.; Kanamori, T.; Nakai, T.; Sasaki, T.; Horiuchi, S.; Sando, S.; Niidome, T. J. Am. Chem. Soc. 2003, 125, 3455–3457.
Nakai, T.; Kanamori, T.; Sando, S.; Aoyama, Y. J. Am. Chem. Soc. 2003, 125, 8465–8475.
Aoyama, Y. Trends Glycosci. Glycotech. 2005, 17, 39–47.
Yamazakia, N.; Kojima, S.; Bovin, N.V.; André, S.; Gabius, S.; Gabius, H.-J. Adv. Drug Del. Rev. 2000, 43, 225–244.
Boussif, O.; Lezoualch, F.; Zanta, M. A.; Mergny, M. D.; Scherman, D.; Demeneix, B.; Behr, J.-P. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7297–7301; Behr, J.-P. Chimia, 1997, 51, 34–36.
Horiuchi, S.; Aoyama, Y. J. Cont. Rel. 2006, 116, 107–114.
Sansone, F.; Baldini, L.; Casnati, A.; Ungaro, R. Supramol. Chem. 2008, 20, 161–168.
Wittmann, V.; Pieters, R. J. Chem. Soc. Rev. 2013, 42, 4492–4503.
Ambrosi, M.; Cameron, N. R.; Davis, B. G. Org. Biomol. Chem. 2005, 3, 1593–1608.
Meunier, S. J.; Roy, R. Tetrahedron Lett. 1996, 37, 5469–5472.
Hayashida, O.; Shimizu, C.; Fujimoto, T.; Aoyama, Y. Chem. Lett. 1998, 13–14.
Hayashida, O.; Nishiyama, K.; Matsuda, Y.; Aoyama, Y. Tetrahedron Lett. 1999, 40, 3407–3410.
Sansone, F.; Chierici, E.; Casnati, A.; Ungaro, R. Org. Biomol. Chem. 2003, 1, 1802–1809.
Roy, R.; Kim, J. M. Angew. Chem. Int. Ed. 1999, 38, 369–372.
Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Mecca, T.; Neri, P. Tetrahedron Lett. 2003, 44, 7467–7470.
Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Sgarlata, V. Org. Lett. 2004, 6, 4163–4166.
Yang, J.; Li, M.; Shen, X.; Liu, S. Viruses 2013, 5, 352–373; Air, G. M. Curr. Op. Virology 2014, 7, 128–133.
Fujimoto, K.; Hayashida, O.; Aoyama, Y.; Guo, C.-T.; Jwa Hidari, K. I.-P.; Suzuki, Y. Chem. Lett. 1999, 1259–1260
Marra, A.; Moni, L.; Pazzi, D.; Corallini, A.; Bridi, D.; Dondoni, A. Org. Biomol. Chem. 2008, 6, 1396–1409.
Dalianis, T.; Hirsch, H. H. Virology 2013, 437, 63–72.
Cecioni, S.; Imberty, A.; Vidal, S. Chem. Rev. 2015, 115, 525–561; Bernardi, A.; Jiménez-Barbero, J.; Casnati, A.; De Castro, C.; Darbre, T.; Fieschi, F.; Finne, J.; Funken, H.; Jaeger, K.-E.; Lahmann, M.; Lindhorst, T. K.; Marradi, M.; Messner, P.; Molinaro, A.; Murphy, P. V.; Nativi, C.; Oscarson, S.; Penadés, S.; Peri, F.; Pieters, R. J.; Renaudet, O.; Reymond, J.-L.; Richichi, B.; Rojo, J.; Sansone, F.; Schäffer, C.; Turnbull, W. B.; Velasco-Torrijos, T.; Vidal, S.; Vincent, S.; Wennekes, T.; Zuilhof, H., Imberty A. Chem. Soc. Rev. 2013, 42, 4709–4727; Audfray, A.; Varrot, A.; Imberty, A. Comp. Rend. Chimie 2013, 16, 482–490.
Loris, R.; Tielker, D.; Jaeger, K.-E.; Wyns, L. J. Mol. Biol. 2003, 331, 861–870.
Boukerb, A. M.; Rousset, A.; Galanos, N.; Méar, J.-B.; Thépaut, M.; Grandjean, T.; Gillon, E.; Cecioni, S.; Abderrahmen, C.; Faure, K.; Redelberger, D.; Kipnis, E.; Dessein, R.; Havet, S.; Darblade, B.; Matthews, S. E.; de Bentzmann, S.; Guéry, B.; Cournoyer, B.; A. Imberty, S. Vidal, J. Med. Chem. 2014, 57, 10275–10289.
Cecioni, S.; Lalor, R.; Blanchard, B.; Praly, J.-P.; Imberty, A.; Matthews, S. E.; Vidal, S. Chem. Eur. J. 2009, 15, 13232–13240.
Cecioni, S.; Praly, J.-P.; Matthews, S. E.; Wimmerová, M.; Imberty, A.; Vidal, S. Chem. Eur. J. 2012, 18, 6250–6263.
Sicard, D.; Cecioni, S.; Iazykov, M.; Chevolot, Y.; Matthews, S. E.; Praly, J.-P.; Souteyrand, E.; Imberty, A.; Vidal, S.; Phaner-Goutorbe, M. Chem. Commun. 2011, 47, 9483–9485.
Sicard, D.; Chevolot, Y.; Souteyrand, E.; Imberty, A.; Vidal, S.; Phaner-Goutorbe, M. J. Mol. Recognit. 2013, 26, 694–699.
Garber, N.; Guempel, U.; Gilboa-Garber, N.; Doyle, R. J. FEMS Micro. Lett. 1987, 48, 331–334.
Cecioni, S.; Faure, S.; Darbost, U.; Bonnamour, I.; Parrot-Lopez, H.; Roy, O.; Taillefumier, C.; Wimmerová, M.; Praly, J.-P.; Imberty, A.; Vidal, S. Chem. Eur. J. 2011, 17, 2146–2159.
Soomro, Z. H.; Cecioni, S.; Blanchard, H.; Praly, J.-P.; Imberty, A.; Vidal, S.; Matthews, S. E. Org. Biomol. Chem. 2011, 9, 6587–6597.
Strutt, N. L.; Zhang, H.; Schneebeli, S. T.; Stoddart, J. F. Acc. Chem. Res. 2014, 47, 2631–2642; Cao, D.; Meier, H. Asian J. Chem. 2014, 3, 244–262; Ogoshi, T.; Yamagishi, T. Eur. J. Org. Chem. 2013, 2961–2975.
Buffet, K.; Nierengarten, I.; Galanos, N.; Gillon, E.; Holler, M.; Imberty, A.; Matthews, S. E.; Vidal, S.; Vincent, S. P.; Nierengarten, J.-F. Chem. Eur. J. 2016, 22, 2955–2963.
Vincent, S. P.; Buffet, K.; Nierengarten, I.; Imberty. A.; Nierengarten, J.-F. Chem. Eur. J. 2016, 22, 88–92.
Moni, L.; Pourceau, G.; Zhang, J.; Meyer, A.; Vidal, S.; Souteyrand, E.; Dondoni, A.; Morvan, F.; Chevolot, Y.; Vasseur, J.-J.; Marra, A. ChemBioChem 2009, 10, 1369–1378.
Consoli, G. M. L.; Granata, G.; Cafiso, V.; Stefani, S.; Geraci, C. Tetrahedron Lett. 2011, 52, 5831–5834.
Nierengarten, I.; Buffet, K.; Holler, M.; Vincent, S. P.; Nierengarten, J.-F. Tetrahedron Lett. 2013, 54, 2398–2402.
Parera Pera, N.; Pieters, R. J. Med. Chem. Commun. 2014, 5, 1027–1035.
Yu, G.; Ma, Y.; Han, C.; Yao, Y.; Tang, G.; Mao, Z.; Gao, C.; Huang, F. J. Am. Chem. Soc. 2013, 135, 10310–10313.
Audfray, A.; Claundinon, J.; Abounit, S.; Ruvoën-Clouet, N.; Larson, G.; Smith, D. F.; Wimmerová, M.; Le Pendu, J.; Römer, W.; Varrot, A.; Imberty, A. J. Biol. Chem. 2012, 287, 4335–4347.
Bernardi, A.; Arosio, D.; Manzoni, L.; Monti, D.; Posteri, H.; Potenza, D.; Mari, S.; Jiménez-Barbero, J. Org. Biomol. Chem. 2003, 1, 785–792.
Arosio, D.; Fontanella, M.; Baldini, L.; Mauri, L.; Bernardi, A.; Casnati, A.; Sansone, F.; Ungaro, R. J. Am. Chem. Soc. 2005, 127, 3660–3661.
Garcia-Hartjes, J.; Bernardi, S.; Weijers, C. A. G. M.; Wennekes, T.; Gilbert, M.; Sansone, F.; Casnati, A.; Zuilhof, H. Org. Biomol. Chem. 2013, 11, 4340–4339.
Pieters, R. J. ChemBioChem 2006, 7, 721–728.
André, S.; Sansone, F.; Kaltner, H.; Casnati, A.; Kopitz, J.; Gabius, H.-J.; Ungaro, R. ChemBioChem 2008, 9, 1649–1661.
André, S.; Grandjean, C.; Gautier, F.-M.; Bernardi, S.; Sansone, F.; Gabius, H.-J.; Ungaro, R. Chem. Commun. 2011, 47, 6126–6128.
Bernardi, S.; Fezzardi, P.; Rispoli, G.; Sestito, S. E.; Peri, F.; Sansone, F.; Casnati, A. Beilstein J. Org. Chem. 2014, 10, 1672–1680.
Cecioni, S.; Matthews, S. E.; Blanchard, H.; Praly, J.-P.; Imberty, A.; Vidal, S. Carbohyd. Res. 2012, 356, 132–141.
Richichi, B.; Comito, G.; Cerofolini, L.; Gabrielli, G.; Marra, A.; Moni, L.; Pace, A.; Pasquato, L.; Chiarugi, P.; Dondoni, A.; Toma, L.; Nativi, C. Bioorg. Med. Chem. 2013, 21, 2756–2763.
Toma, L.; Di Cola, E.; Ienco, A.; Legnani, L.; Lunghi, C.; Moneti, G.; Richichi, B.; Ristori, S.; Dell’Atti, D.; Nativi, C. ChemBioChem 2007, 8, 1646–1649; Arcangeli, A.; Toma, L.; Contiero, L.; Crociani, O.; Legnani, L.; Lunghi, C.; Nesti, E.; Moneti, G.; Richichi, B.; Nativi, C. Bioconj. Chem. 2010, 21, 1432–1438.
Iida, J.; Meijne, A. M. L.; Knutson, J. R.; Furch, L. T.; McCarthy, J. B. Sem. Cancer Biol. 1996, 7, 155–162.
Tomita, N.; Sando, S.; Sera, T.; Aoyama, Y. Bioorg. Med. Chem. Lett. 2004, 14, 2087–2090.
Křenek, K.; Kuldová, M.; Hulíková, K.; Stibor, I.; Lhoták, P.; Dudič, M.; Budka, J.; Pelantová, H.; Bezouška, K.; Fišerová, A.; Křena, V. Carbohydr. Res. 2007, 342, 1781–1792.
Fujimoto, T.; Shimizu, C.; Hayashida, O.; Aoyama, Y. J. Am. Chem. Soc. 1998, 120, 601–602.
Fujimoto, K.; Miyata, T.; Aoyama, Y. J. Am. Chem. Soc. 2000, 122, 3558–3559.
Aleandri, S.; Casnati, A.; Fantuzzi, L.; Mancini, G.; Rispoli, G.; Sansone, F. Org. Biomol. Chem. 2013, 11, 4811–4817.
Avvakumova, S.; Fezzardi, P.; Pandolfi, L.; Colombo, M.; Sansone, F.; Casnati, A.; Prosperi, D. Chem. Commun. 2014, 50, 11029–11032.
Salvati, A.; Pitek, A. S.; Monopoli, M. P.; Prapainop, K.; Baldelli Bombelli, F.; Hristov, D. R.; Kelly, P. M.; Åberg, C.; Mahon, E.; Dawson, K. A. Nat. Nanotech. 2013, 137–145.
Harrison, J. C.; Eftink, M. R. Biopolymers 1982, 21, 1153–1166.
Gallego-Yerga, L.; Lomazzi, M.; Sansone, F.; Ortiz Mellet, C.; Casnati, A.; Garcıa Fernandez, J. M. Chem. Commun. 2014, 50, 7440–7443.
Geraci, C.; Consoli, G. M. L.; Galante, E.; Bousquet, E.; Pappalardo, M.; Spadaro, A. Bioconj. Chem. 2008, 19, 751–758.
Kim, Y. J.; Varki, A. Glycoconjugate J. 1997, 14, 569–576; Peri, F. Chem. Soc. Rev. 2013, 42, 4543–4556; Shiao, T. C.; Roy, R. New. J. Chem. 2012, 36, 324–339.
Giorgi, M. E.; de Lederkremer, R. M. Carbohydr. Res. 2011, 346, 1389–1393; Neres, J.; Brewer, M. L.; Ratier, L.; Botti, H.; Buschiazzo, A.; Edwards, P. N.; Mortenson, P. N.; Charlton, M. H.; Alzari, P. M.; Frasch, A. C.; Bryce, R. A.; Douglas, K. T. Bioorg. Med. Chem. Lett. 2009, 19, 589–596.
Galante, E.; Geraci, C.; Sciuto, S.; Campo, V. L.; Carvalho, I.; Sesti-Costa, R.; Guedes, P. M. M.; Silva, J. S.; Hill, L.; Nepogodiev, S. A.; Field, R. A. Tetrahedron 2011, 67, 5902–5912.
Viola, S.; Consoli, G. M. L.; Merlo, S.; Drago, F.; Sortino, M. A.; Geraci, C. J. Neurochem. 2008, 107, 1047–1055.
Viola, S.; Merlo, S.; Consoli, G. M. L.; Drago, F.; Geraci, C.; Sortino, M. A. Pharmacology 2010, 86, 182–188.
Micali, N.; Villari, V.; Consoli, G. M. L.; Cunsolo, F.; Geraci, C. Phys. Rev. E 2006, 73, 051904.
Cardona, F.; Isoldi, G.; Sansone, F.; Casnati, A.; Goti, A. J. Org. Chem. 2012, 77, 6980–6988.
Marradi, M.; Cicchi, S.; Sansone, F.; Casnati, A.; Goti, A. Beilstein J. Org. Chem. 2012, 8, 951–957.
Brissonnet, Y.; Ortiz Mellet, C.; Morandat, S.; Garcia Moreno, M. I.; Deniaud, D.; Matthews, S. E.; Vidal, S.; Šesták, S.; El Kirat, K.; Gouin, S. G. J. Am. Chem. Soc. 2013, 135, 18427–18435.
Marra, A.; Zelli, R.; D’Orazio, G.; La Ferla, B.; Dondoni, A. Tetrahedron 2014, 70, 9387–9393.
Horne, G.; Wilson, F. X.; Tinsley, J.; Williams, D. H.; Storer, R. Drug Discovery Today 2011, 16, 107–118.
Nash, R. J.; Kato, A.; Yu, C.-Y.; Fleet, G. W. J. Future Med. Chem. 2011, 3, 1513–1521.
Ficicioglu, C. Therapeutics and Clinical Risk Management 2008, 4, 425–431.
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Matthews, S.E. (2016). Calixsugars: Finally Reaching Their Therapeutic Potential?. In: Neri, P., Sessler, J., Wang, MX. (eds) Calixarenes and Beyond. Springer, Cham. https://doi.org/10.1007/978-3-319-31867-7_22
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