An Efficient and General Route to the Synthesis of Novel Aminoglycosides for RNA Binding

Abstract

An alternative and straightforward method to prepare aminoglycoside dimers and heterodimeric conjugates is reported. The novel type of modification may provide a promising way for the development of new ligands effectively targeting to RNA.

aminoglycoside - azide - oligosaccharide synthesis - ­antibiotics - drug design

References and Notes

<A NAME="RG30410ST-1">1</A>

New address: Instituto de Productos Naturales y Agrobiología, Avd. Astrof. F. Sánchez, 3 38205 San Cristóbal de La Laguna (Santa Cruz de Tenerife), Spain.

<A NAME="RG30410ST-2">2</A> Aminoglycoside Antibiotics: From Chemical Biology to Drug Discovery   Arya DP. Wiley-Interscience; Hoboken: 2007. 

<A NAME="RG30410ST-3">3</A> Magnet S. Blanchard JS. Chem. Rev.  2005,  477 

<A NAME="RG30410ST-4">4</A> Selimoglu E. Curr. Pharm. Des.  2007,  119 

<A NAME="RG30410ST-5">5</A> Houghton JL. Green KD. Chen W. Garneau-Tsodikova S. ChemBioChem  2010,  880 

<A NAME="RG30410ST-6A">6a</A> Revuelta J. Vacas T. Corzana F. González C. Bastida A. Asensio JL. Chem. Eur. J.  2010,  2986 

<A NAME="RG30410ST-6B">6b</A> Vourloumis D. Winters GC. Simonsen KB. Takahashi M. Ayida BK. Sándwick S. Zhao Q. Han Q. Hermann T. ChemBioChem  2005,  58 

<A NAME="RG30410ST-6C">6c</A> Ye X.-S. Zhang L.-H. Curr. Med. Chem.  2002,  929 

<A NAME="RG30410ST-7A">7a</A> Chen G.-H. Pan P. Chen Y. Meng X.-B. Li Z.-J. Tetrahedron  2009,  5922 

<A NAME="RG30410ST-7B">7b</A> Bodlenner A. Alix A. Weibel J.-M. Pale P. Ennifar E. Paillart J.-C. Walter P. Marquet R. Dumas P. Org. Lett.  2007,  4415 

<A NAME="RG30410ST-7C">7c</A> Kondo J. Hainrichson M. Nudelman I. Shallom-Shezifi D. Barbieri CM. Pilch DS. Westhof E. Baasov T. ChemBioChem  2007,  1700 

<A NAME="RG30410ST-7D">7d</A> Riguet E. Désiré J. Boden O. Ludwig V. Göbel M. Bailly C. Décout J.-I. Bioorg. Med. Chem. Lett.  2005,  4651 

<A NAME="RG30410ST-7E">7e</A> Agnelli F. Sucheck SJ. Marby KA. Rabuka D. Yao S.-L. Sears PS. Liang F.-S. Wong C.-H. Angew. Chem. Int. Ed.  2004,  1562 

<A NAME="RG30410ST-7F">7f</A> Tok JB.-H. Fenker J. Bioorg. Med. Chem. Lett.  2001,  2987 

<A NAME="RG30410ST-7G">7g</A> Sucheck SJ. Wong AL. Koeller KM. Boehr DD. Draker D.-A. Sears P. Wright GD. Wong C.-H. J. Am. Chem. Soc.  2000,  5230 

<A NAME="RG30410ST-7H">7h</A> Michael K. Wang H. Tor Y. Bioorg. Med. Chem.  1999,  1361 

<A NAME="RG30410ST-7I">7i</A> Wang H. Tor Y. Bioorg. Med. Chem. Lett.  1997,  1951 

<A NAME="RG30410ST-8">8</A> Litovchick A. Evdokimov AG. Lapidot A. Biochemistry  2000,  2838 

<A NAME="RG30410ST-9">9</A> Werstuck G. Zapp ML. Green MR. Chem. Biol.  1996,  129 

<A NAME="RG30410ST-10A">10a</A> Wu S. Fu Y. Yan R. Wu Y. Lei X. Ye X.-S. Tetrahedron  2010,  3433 

<A NAME="RG30410ST-10B">10b</A> Lee J. Kwon M. Lee KH. Jeong S. Hyun S. ShIn KJ. Ju J. J. Am. Chem. Soc.  2004,  1956 

<A NAME="RG30410ST-10C">10c</A> Francois B. Szychowski J. Adhikari SS. Pachamuthu K. Swayze EE. Griffey RH. Migawa MT. Westhof E. Hanessian S. Angew. Chem. Int. Ed.  2004,  6735 

<A NAME="RG30410ST-10D">10d</A> Ding Y. Hofstadler SA. Swayze EE. Risen L. Griffey RH. Angew. Chem. Int. Ed.  2003,  3409 

<A NAME="RG30410ST-10E">10e</A> Ding Y. Hofstadler SA. Swayze EE. Griffey RH. Org. Lett.  2001,  1621 

<A NAME="RG30410ST-10F">10f</A> Wong C.-H. Hendrix M. Manning DD. Rosenbohm C. Greenberg WA. J. Am. Chem. Soc.  1998,  8319 

<A NAME="RG30410ST-11A">11a</A> Alguacil J. Defaus S. Claudio A. Trapote A. Masides M. Robles J. Eur. J. Org. Chem.  2010,  3102 

<A NAME="RG30410ST-11B">11b</A> Mei H. Xing L. Cai L. Jin H.-W. Zhao P. Yang Z.-J. Zhang L.-H. Bioorg. Med. Chem. Lett.  2008,  5355 

<A NAME="RG30410ST-11C">11c</A> Cai L. Li Q. Ren B. Yang Z.-J. Zhang L.-R. Zhang L.-H. Tetrahedron  2007,  8135 

<A NAME="RG30410ST-11D">11d</A> Chares I. Xi H. Arya DP. Bioconjugate Chem.  2007,  160 

<A NAME="RG30410ST-11E">11e</A> Hyun S. Lee KH. Yu J. Bioorg. Med. Chem. Lett.  2006,  4757 

<A NAME="RG30410ST-11F">11f</A> Charles I. Xue L. Arya DP. Bioorg. Med. Chem. Lett.  2002,  1259 

<A NAME="RG30410ST-12">12</A> Fourmy D. Recht MI. Puglisi D. J. Mol. Biol.  1998,  347 

<A NAME="RG30410ST-13A">13a</A> Fourmy D. Recht MI. Blanchard SC. Puglisi JD. Science  1996,  1367 

<A NAME="RG30410ST-13B">13b</A> Carter AP. Clemons WM. Brodersen DE. Morgan-Warren RJ. Wimberly BT. Ramakrishnan V. Nature  2000,  340 

<A NAME="RG30410ST-13C">13c</A> Vicens Q. Westhof E. Chem. Biol.  2002,  747 

<A NAME="RG30410ST-13D">13d</A> Francois B. Rusell RJM. Murray JB. Aboul-ela F. Masquida B. Vicens Q. Westhof E. Nucleic Acid Res.  2005,  33:  5677 

<A NAME="RG30410ST-13E">13e</A> Kondo J. Russell RJM. Murray JB. Westhof E. Biochimie  2006,  1027 

<A NAME="RG30410ST-13F">13f</A> Vicens Q. Westhof E. Structure  2001,  647 

<A NAME="RG30410ST-14">14</A> Wang H. Tor Y. J. Am. Chem. Soc.  1997,  8734 

<A NAME="RG30410ST-15A">15a</A> Alper PB. Hung S.-C. Wong C.-H. Tetrahedron Lett.  1996,  6029 

<A NAME="RG30410ST-15B">15b</A> Nyffeler PT. Liang G.-H. Koeller KM. Wong C.-H. J. Am. Chem. Soc.  2002,  10773 

<A NAME="RG30410ST-16">16</A> Titz A. Radic Z. Schawardt O. Ernst D. Tetrahedron Lett.  2006,  2383 

<A NAME="RG30410ST-17">17</A> Yan R.-B. Yang F. Wu Y. Zhang L.-H. Yen X.-S. Tetrahedron Lett.  2005,  8993