Development of New Methodologies for Entry to Targets of Therapeutic Interest

Helen M. I. Osborn

doi:10.1055/s-2005-917076

ACCOUNT

Development of New Methodologies for Entry to Targets of Therapeutic Interest

Helen M. I. Osborn*
School of Pharmacy, University of Reading, Whiteknights, Reading, RG6 6AD, UK
Fax: +44(118)3786331; e-Mail: h.m.i.Osborn@rdg.ac.uk;

Abstract

All articles of this category

Abstract

This Account provides an overview of strategies that have been reported from our laboratories for the synthesis of targets of therapeutic interest, namely carbohydrates, and prodrugs for the treatment of melanoma. These programmes have involved the development of new synthetic methodologies including the regio- and stereoselective synthesis of specific carbohydrate isomers, and new protecting group methodologies. This review provides an insight into the progress of these research themes, and suggests some applications for the targets that are currently being explored.

1 Carbohydrate Targets
1.1 The Development of Regioselective Protection and Glycosidation Protocols
1.2 The Stereoselective Synthesis of α-Linked GlcNAc and
β-Linked ManNAc Residues
1.3 Development of Methodology for the Synthesis of Multivalent Carbohydrate Arrays
1.4 Development of Methodology for the Synthesis of Glycosidase Inhibitors
2 The Design and Analysis of Novel Prodrugs for the Treatment of Melanoma
3 Development of Tyrosinase Labile Protecting Groups for Amines

Key words

carbohydrates - prodrugs - regioselective - stereoselective - melanoma

Full Text

References

For example see:

<A NAME="RA38305ST-1A">1a</A> Koeller KM. Wong C.-H. Nature Biotechnol. 2000, 18: 835

<A NAME="RA38305ST-1B">1b</A> Bertozzi CR. Kiessling LL. Science 2001, 291: 2357

<A NAME="RA38305ST-1C">1c</A> Davis BG. Chem. Rev. 2002, 102: 579

<A NAME="RA38305ST-1D">1d</A> Dwek RA. Butters TD. Chem. Rev. 2002, 102: 283

<A NAME="RA38305ST-1E">1e</A> Werz DB. Seeberger PH. Chem.-Eur. J. 2005, 11: 3194

<A NAME="RA38305ST-2">2</A> For a recent overview of carbohydrate protecting group strategies see: Robertson J. Stafford PM. In Carbohydrates: Best Synthetic Methods Academic Press; London: 2003. Chap. 2.

For example see:

<A NAME="RA38305ST-3A">3a</A> Haines AH. Adv. Carbohydr. Chem. Biochem. 1976, 33: 11

<A NAME="RA38305ST-3B">3b</A> Haines AH. Adv. Carbohydr. Chem. Biochem. 1981, 39: 13

For example see:

<A NAME="RA38305ST-4A">4a</A> Yu B. Yang ZY. Cao HZ. Curr. Org. Chem. 2005, 9: 179

<A NAME="RA38305ST-4B">4b</A> Baeschlin DK. Green LG. Hahn MG. Hinzen B. Ince SJ. Ley SV. Tetrahedron: Asymmetry 2000, 11: 173

<A NAME="RA38305ST-4C">4c</A> Grice P. Ley SV. Osborn HMI. Priepke HWM. Warriner SL. Chem.-Eur. J. 1997, 3: 431

<A NAME="RA38305ST-4D">4d</A> Wong CH. Mong KKT. Angew. Chem. Int. Ed. 2002, 41: 4087

For example see:

<A NAME="RA38305ST-5A">5a</A> Bashir NB. Phythian SJ. Reason AJ. Roberts SM. J. Chem. Soc., Perkin Trans. 1 1995, 2203

<A NAME="RA38305ST-5B">5b</A> Chinn MJ. Iacazio G. Spackman DG. Turner NJ. Roberts SM. J. Chem. Soc., Perkin Trans. 1 1992, 661

<A NAME="RA38305ST-5C">5c</A> Iacazio G. Roberts SM. J. Chem. Soc., Perkin Trans. 1 1993, 1099

<A NAME="RA38305ST-5D">5d</A> Panza L. Brasca S. Riva S. Russo G. Tetrahedron: Asymmetry 1993, 4: 931

<A NAME="RA38305ST-6A">6a</A> Gridley JJ. Hacking AJ. Osborn HMI. Spackman DG. Synlett 1997, 1397

<A NAME="RA38305ST-6B">6b</A> Gridley JJ. Hacking AJ. Osborn HMI. Spackman DG. Tetrahedron 1998, 54: 14925

<A NAME="RA38305ST-7A">7a</A> Eby R. Schuerch C. Carbohydr. Res. 1982, 100: C41

<A NAME="RA38305ST-7B">7b</A> Eby R. Webster KT. Schuerch C. Carbohydr. Res. 1984, 129: 111

<A NAME="RA38305ST-7C">7c</A> Avela E. Melander B. Holmbom B. Acta Acad. Abstr., Ser. B 1971, 14: 31

<A NAME="RA38305ST-8A">8a</A> Osborn HMI. Brome VA. Harwood LM. Suthers WG. Carbohydr. Res. 2001, 332: 157

<A NAME="RA38305ST-8B">8b</A> Gridley JJ. Osborn HMI. Suthers WG. Tetrahedron Lett. 1999, 40: 6991

<A NAME="RA38305ST-9A">9a</A> Garegg PJ. Maloisel J.-L. Oscarson S. Synthesis 1995, 409

<A NAME="RA38305ST-9B">9b</A> Garegg PJ. Olsson L. Oscarson S. Bioorg. Med. Chem. 1996, 4: 1867

<A NAME="RA38305ST-9C">9c</A> Kaji E. Harta N. Tetrahedron Lett. 2000, 41: 53

<A NAME="RA38305ST-10">10</A> Evans PG. Osborn HMI. Suthers WG. Tetrahedron Lett. 2002, 43: 7855

<A NAME="RA38305ST-11">11</A> For a useful review see: Kaji E. Lichtenthaler FW. Trends Glycosci. Glycotechnol. 1993, 5: 121

<A NAME="RA38305ST-12">12</A> Gridley JJ. Osborn HMI. J. Chem. Soc., Perkin Trans. 1 2000, 1471

For recent examples see:

<A NAME="RA38305ST-13A">13a</A> Crich D. Li WJ. Li HM. J. Am. Chem. Soc. 2004, 126: 15081

<A NAME="RA38305ST-13B">13b</A> Crich D. Banerjee A. Yao QJ. J. Am. Chem. Soc. 2004, 126: 14930

<A NAME="RA38305ST-14A">14a</A> Drew MGB. Ennis SC. Gridley JJ. Osborn HMI. Spackman DG. Tetrahedron 2001, 57: 7919

<A NAME="RA38305ST-14B">14b</A> Ennis SC. Gridley JJ. Osborn HMI. Spackman DG. Synlett 2000, 1593

<A NAME="RA38305ST-15A">15a</A> Mulvey G. Kitov PI. Marcato P. Bundle DR. Armstrong GD. Biochimie 2001, 83: 841

<A NAME="RA38305ST-15B">15b</A> Zopf D. Roth S. Lancet 1996, 347: 1017

<A NAME="RA38305ST-16A">16a</A> Mouricout M. Petit JM. Carias JR. Julien R. Infect. Immun. 1990, 58: 98

<A NAME="RA38305ST-16B">16b</A> Griemel P. Spreitz J. Stutz AE. Wrodnigg TM. Curr. Top. Med. Chem. 2003, 3: 513

<A NAME="RA38305ST-17A">17a</A> Ofek I. Sharon N. Curr. Top. Microbiol. Immunol. 1990, 151: 91

<A NAME="RA38305ST-17B">17b</A> Ofek I. Mirelman D. Sharon N. Nature (London) 1977, 265: 623

<A NAME="RA38305ST-17C">17c</A> Ofek I. Beachey EH. Infect. Immun. 1978, 22: 247

For example see:

<A NAME="RA38305ST-18A">18a</A> Ashton PR. Hounsell EF. Jayaraman N. Nilsen TM. Spencer N. Stoddart JF. Young M. J. Org. Chem. 1998, 63: 3429

<A NAME="RA38305ST-18B">18b</A> Corbell JB. Lundquist JJ. Toone EJ. Tetrahedron: Asymmetry 2000, 11: 95

<A NAME="RA38305ST-18C">18c</A> Page D. Roy R. Bioconjugate Chem. 1997, 8: 10

<A NAME="RA38305ST-19">19</A> Firon N. Ofek I. Sharon N. Infect. Immun. 1984, 43: 1088

<A NAME="RA38305ST-20">20</A> Madiyalakan R. Chowdhary MS. Rana SS. Matta KL. Carbohydr. Res. 1986, 152: 183

<A NAME="RA38305ST-21">21</A> Suwasono S. Rastall RA. Biotech. Lett. 1996, 18: 851

For relevant examples see:

<A NAME="RA38305ST-22A">22a</A> MacLeod JM. Carbohydr. Res. 1979, 75: 71

<A NAME="RA38305ST-22B">22b</A> Gaucher SP. Pedersen SF. Leary JA. J. Org. Chem. 1999, 64: 4012

<A NAME="RA38305ST-23">23</A> Hayes W. Romagnoli B. Harwood LM. Philp D. Price DW. Smith M. Tetrahedron Lett. 2003, 44: 37

<A NAME="RA38305ST-24A">24a</A> Hayes W. Osborn HMI. Osborne SD. Rastall RA. Romagnoli B. Tetrahedron Lett. 2003, 44: 37

<A NAME="RA38305ST-24B">24b</A> Hayes W. Osborn HMI. Osborne SD. Rastall RA. Romagnoli B. Tetrahedron 2003, 59: 7983

For example see:

<A NAME="RA38305ST-25A">25a</A> Lillelund VH. Jensen HH. Liang XF. Bols M. Chem. Rev. 2002, 102: 515

<A NAME="RA38305ST-25B">25b</A> Asano N. Nash RJ. Molyneux RJ. Fleet GWJ. Tetrahedron: Asymmetry 2000, 11: 1645

<A NAME="RA38305ST-25C">25c</A> El Ashry ESH. Rashed N. Shobier AHS. Pharmazie 2000, 55: 251

For example see:

<A NAME="RA38305ST-26A">26a</A> Sinnott ML. Chem. Rev. 1990, 90: 1171

<A NAME="RA38305ST-26B">26b</A> Wong C.-H. Halcomb RL. Ichikawa Y. Kajimoto T. Angew. Chem., Int. Ed. Engl. 1995, 34: 521

<A NAME="RA38305ST-26C">26c</A> Legler G. Adv. Carbohydr. Chem. Biochem. 1990, 48: 319

<A NAME="RA38305ST-27">27</A> Jordan AM. Osborn HMI. Stafford PM. Tzortzis G. Rastall RA. J. Carb. Chem. 2003, 22: 705

<A NAME="RA38305ST-28">28</A> For a recent review of the Ferrier reaction see: Ferrier RJ. Top. Curr. Chem. 2001, 215: 153

For example see:

<A NAME="RA38305ST-29A">29a</A> Vogel P. Chimia 2001, 55: 359

<A NAME="RA38305ST-29B">29b</A> Weatherman RV. Kiessling LL. J. Org. Chem. 1996, 61: 534

<A NAME="RA38305ST-29C">29c</A> Weatherman RV. Mortell KH. Chevenak M. Kiessling LL. Toone EJ. Biochemistry 1996, 35: 3619

<A NAME="RA38305ST-30">30</A> Gemmell N. Osborn HMI. Meo P. Org. Lett. 2003, 5: 1649

<A NAME="RA38305ST-31">31</A> Brimble MA. Brenstrum TJ. J. Chem. Soc., Perkin Trans. 1 2001, 1612

<A NAME="RA38305ST-32">32</A> Clark SM. Osborn HMI. Tetrahedron: Asymmetry 2004, 15: 3643

<A NAME="RA38305ST-33A">33a</A> Herreros E. Almela MJ. Lozano S. De Las Heras FG. Gargallo-Viola D. Antimicrob. Agents Chemother. 2001, 45: 3132

<A NAME="RA38305ST-33B">33b</A> Okazaki S. Shirai N. Sato Y. J. Org. Chem. 1990, 55: 334

<A NAME="RA38305ST-34">34</A> Osborn HMI. Evans PG. Gemmell N. Osborne SD. J. Pharm. Pharmacol. 2004, 56: 691

<A NAME="RA38305ST-35">35</A> For a recent review see: Rooseboom M. Commandeur JNM. Vermeulen NPE. Pharmacol. Rev. 2004, 56: 53

For recent reviews see

<A NAME="RA38305ST-36A">36a</A> Rooseboom M. Commandeur JNM. Vermeulen NPE. Pharmacol. Rev. 2004, 56: 53

<A NAME="RA38305ST-36B">36b</A> Tietze LF. Feverstein T. Curr. Pharm. Des. 2003, 9: 2155

<A NAME="RA38305ST-36C">36c</A> Goodwin DA. Meares CF. Biotechnol. Adv. 2001, 19: 435

<A NAME="RA38305ST-36D">36d</A> Syrigos KN. Epenetos AA. Anticancer Res. 1999, 19: 605

<A NAME="RA38305ST-37A">37a</A> Ito Y. Jimbow K. Cancer Res. 1987, 47: 3278

<A NAME="RA38305ST-37B">37b</A> Morrison ME. Yagi MJ. Cohen G. Proc. Natl. Acad. Sci. U.S.A. 1985, 82: 2960

<A NAME="RA38305ST-37C">37c</A> Riley PA. Pigment Cell Res. 2003, 16: 548

<A NAME="RA38305ST-38A">38a</A> Jordan AM. Khan TH. Osborn HMI. Photiou A. Riley PA. Bioorg. Med. Chem. 1999, 7: 1775

<A NAME="RA38305ST-38B">38b</A> Jordan AM. Khan TH. Malkin H. Osborn HMI. Photiou A. Riley PA. Bioorg. Med. Chem. 2001, 9: 1549

<A NAME="RA38305ST-38C">38c</A> Jordan AM. Khan TH. Malkin H. Osborn HMI. Bioorg. Med. Chem. 2002, 10: 2625

For details of melanin biosynthesis see:

<A NAME="RA38305ST-39A">39a</A> Riley PA. Eur. J. Cancer 1991, 27: 1172

<A NAME="RA38305ST-39B">39b</A> Jimbow K. Iwashina T. Alena F. Yamada K. Panchovich J. Umemura T. J. Invest. Dermatol. 1993, 100: 231

<A NAME="RA38305ST-39C">39c</A> Pawelek J. Korner A. Bergstrom A. Bologna J. Nature (London) 1980, 286: 617

<A NAME="RA38305ST-39D">39d</A> Land EJ. Ramsden CA. Riley PA. Methods Enzymol. 2004, 378: 88

<A NAME="RA38305ST-40A">40a</A> Schoot-Uiterkamp AJM. Mason HS. Proc. Natl. Acad. Sci. U. S. A. 1973, 70: 993

<A NAME="RA38305ST-40B">40b</A> Nishioka K. Eur. J. Biochem. 1978, 85: 137

<A NAME="RA38305ST-41">41</A> Osborn HMI. Williams NAO. Org. Lett. 2004, 6: 3111

For recent reviews see:

<A NAME="RA38305ST-42A">42a</A> Kadereit DK. Waldmann H. Chem. Rev. 2001, 101: 3367

<A NAME="RA38305ST-42B">42b</A> Kadereit D. Waldmann H. Monatsh. Chem. 2000, 131: 571

<A NAME="RA38305ST-43">43</A> For a recent review see: Land EJ. Ramsden CA. Riley PA. Acc. Chem. Res. 2003, 36: 300