Synthetic analogs of natural glycosides in drug discovery and development

Acta Poloniae Pharmaceutica - Drug Research

Volumn 65, Issue 6, 2008, Pages 655-676

  Grynkiewicz, Grzegorz ^a,c   Szeja, Wiesław ^b   Boryski, Jerzy ^a  

^a INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^b SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

Author keywords

Chemical glycosylation; Glycosidic drugs; Modification of sugar moieties; Natural products; Naturally occurring glycosides; Secondary metabolites

Indexed keywords

AMPHOTERICIN; AMRUBICIN; AVERMECTIN; AZITHROMYCIN; BLEOMYCIN; CALICHEAMICIN; COLCHICINE; DAUNORUBICIN; DOXORUBICIN; ENEDIYNE; ERYTHROMYCIN; GLYCOSIDE; LINCOMYCIN; MACROLIDE; MORPHINE; NUCLEOSIDE DERIVATIVE; NYSTATIN; POLYPHENOL DERIVATIVE; REBECCAMYCIN; SALICIN; SAPONIN DERIVATIVE; SOLANINE; STAUROSPORINE; STEROL DERIVATIVE; TERPENOID DERIVATIVE; THIOCOLCHICOSIDE; TOMATINE; UNINDEXED DRUG; VANCOMYCIN; ZINOSTATIN; DRUG; PLANT EXTRACT;

BIOTECHNOLOGY; DRUG DESIGN; DRUG EFFICACY; DRUG SELECTIVITY; DRUG SYNTHESIS; ETHNOPHARMACOLOGY; GLYCOSYLATION; GOUT; REVIEW; CHEMISTRY; HUMAN; MEDICINAL PLANT; METHODOLOGY; PHARMACOGNOSY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

DRUG DESIGN; GLYCOSIDES; HUMANS; PHARMACEUTICAL PREPARATIONS; PHARMACOGNOSY; PLANT EXTRACTS; PLANTS, MEDICINAL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 61549101804     PISSN: 00016837     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (124)

1. Taylor M.E., Drickamer K.: Introduction to Glycobiology, Oxford University Press, Oxford 2003.
2. Comprehensive Glycoscience; From Chemistry to Systems Biology. Kamerling J.P. Ed., Elsevier, Amsterdam 2007.
3. Samuelsson G.: Drugs of natural origin, 4th ed., Apotekarsocieten, Stockholm 1999.
4. Plotkin M.J.: Medicine Quest: In search of Natureís Healing Secrets, Viking, New York 2000.
5. Kołodziejczyk A.: Natural organic compounds (in Polish), PWN, Warszawa 2004.
6. Secondary Metabolism in Model Systems; Recent Advances in Phytochemistry, vol. 38, Romeo J.T. Ed., Elsevier, Amsterdam 2004.
7. Harborne J.: Ecological biochemistry (Polish translation), PWN, Warszawa 1997.
8. Oleszek W., Glowniak K., Leszczynski B. Eds.: Biochemical environmental interactions (in Polish), AM, Lublin 2001.
9. th ed., W.B. Saunders, Edinburgh, 2002.
10. Weymouth-Wilson A.C.: Nat. Prod. Rep. 14, 99 (1997).
11. Křen V., Martinkova L.: Curr. Med. Chem. 8, 1313 (2001).
12. Thorson J.S., Vogt T.: in Carbohydrate-based Drug Discovery, Wong C-H. Ed., vol 1, p. 685, Wiley-VCH, Weinheim 2003.
13. Cutler S.J, Cutler H.G. Eds., Biologically active natural products, CRC Press, Boca Raton 2000.
14. Goodman L,: Adv. Carbohydr. Chem. 22, 109 (1967).
15. Lemieux R.U.: Adv. Carbohydr. Chem. 9, 1 (1954).
16. Schmidt R.R.: Angew. Chem. Int. Ed. Engl. 25, 212 (1986).
17. Garegg P.J.: Adv. Carbohydr. Chem. Biochem. 52, 174 (1997).
18. Mukaiyama T.: Angew. Chem. Int. Ed. Engl. 43, 5590 (2004).
19. Handbook of Chemical Glycosylation, Demchenko A.V. Ed., Wiley-VCH, Weinheim, New York 2008.
20. Shoda S.I.: in Handbook of Chemical Glycosylation, Demchenko A.V. Ed., p. 29, Wiley- VCH, Weinheim, New York 2008.
21. Ryan D.A., Gin D.Y.: in Handbook of Chemical Glycosylation, Demchenko A.V. Ed., p. 95, Wiley-VCH, Weinheim, New York 2008.
22. Szeja W., Grynkiewicz G.: in Handbook of Chemical Glycosylation, Demchenko A.V. Ed., p. 329, Wiley-VCH, Weinheim, New York 2008.
23. Kim K.S., Jeon H.B.: in Handbook of Chemical Glycosylation, Demchenko A.V. Ed., p. 185, Wiley-VCH, Weinheim, New York 2008.
24. Friesen R.W., Danishefsky S.J.: J. Am. Chem. Soc. 111, 6656 (1989).
25. Halcomb R.L,: Danishefsky S.J.: J. Am. Chem. Soc. 111, 6661 (1989).
26. Lemieux R.U., Hendriks K.B., Stick R.V., James K.: J. Am. Chem. Soc. 97, 4056 (1975).
27. Veeneman G.H., van Leeuwen S.H., van Boom J.H.: Tetrahedron Lett. 31, 1334 (1990).
28. Paulsen H.: Angew. Chem. Int. Ed. Engl. 21, 155 (1982).
29. Crich D., Sun S.: J. Org. Chem. 61, 4506 (1996).
30. Crich D., Smith M.: Org. Lett. 2, 4067 (2000).
31. Anderson F., Fugedi P., Garegg P.J., Nashed M:. Tetrahedron Lett. 27, 3019 (1986).
32. Garegg P.J., Oscarson S., Szonyi H.: Carbohydr. Res. 205, 125 (1990).
33. Toshima K., Tatsuta K.: Chem. Rev. 93, 1503 (1993).
34. Pellissier M.: Tetrahedron 61, 2947 (2005).
35. Paulsen H.: Angew. Chem., Int. Ed. Engl. 21, 184 (1982).
36. Needs P. W., Williamson G.: Carbohydr. Res. 330, 511 (2001).
37. Bouktaib M., Atmani A., Rolando C.: Tetrahedron Lett. 43, 6263 (2002).
38. Nishida Y., Ohrui H., Meguro H., Ishizawa M., Matsuda K., Taki T., Handa S., Yamamoto N.: Tetrahedron Lett. 35, 5465 (1994).
39. Wang C.C., Lee J.C., Luo S.Y., Fan H.F., Pai C.L., Yang W.C., Lu L.D., Hung S.C.: Angew. Chem., Int. Ed. Engl. 41, 2360 (2002).
40. Nikolakakis A., Haidara K., Sauriol F., Mamer O., Zamir L.O.: Biorg. Med. Chem. 11, 1551 (2003).
41. Kanie O., Ito Y., Ogawa T.: Tetrahedron Lett. 37, 4551 (1996).
42. Kopper S., Thiem J.: Carbohydr. Res. 260, 219 (1994).
43. Messaoudi S., Anizon F., Pfeiffer B., Golsteyn R., Prudhomme M.: Tetrahedron Lett. 45, 4643 (2005).
44. Grabley S., Thiericke R. Eds.: Drug discovery from nature, Springer, Berlin 2000.
45. Butler M.S.: Nat. Prod. Rep. 22, 162 (2005).
46. Booser D.J., Hortobagyi G.N.: Drugs 47, 223 (1994).
47. Monneret C.: Eur J. Med. Chem. 36, 483 (2001).
48. Minotti G., Menna P., Salvatorelli E., Cairo G., Gianni L.: Pharmacol Rev. 56, 185 (2004).
49. Anthracycline Chemistry and Biology, Krohn K. Ed., Topics in Current Chemistry, Vol. 282 and 283, Springer, Berlin 2008.
50. Priebe W., Perez-Soler R.: Pharmacol. Ther. 60, 215 (1993).
51. Priebe W.: Curr. Drug Design 1, 73 (1995).
52. Chaires J.B., Satyanarayana S., Suh D., Fokt I., Przewloka T., Priebe W.: Biochemistry 35, 2047 (1996).
53. Priebe W., Van N., Burke T.G., Perez-Soler R.: Anticancer Drugs 4, 37 (1993).
54. Otsomaa L.A., Koskinen A.M.P.: Fortschr. Chem. Org. Naturst. 74, 197 (1998).
55. Grynkiewicz G., Szeja W.: Top. Curr. Chem. 282, 249 (2008).
56. Grynkiewicz G., Achmatowicz O., Fokt I., Priebe W., Ramza J., Szechner B., Szeja W.: Wiad. Chem. 56, 536 (2002).
57. Grynkiewicz G., Fokt I., Skibicki P., Przewloka T., Szeja W., Priebe W.: Polish J. Chem. 79, 335 (2005).
58. Fang L., Zhang G., Li C., et al.: J. Med. Chem. 49, 932 (2006).
59. Grynkiewicz G., Achmatowicz O., Hennig J., Indulski J., Klessig D.F.: Polish J. Chem. 67, 965 (1993).
60. Hanessian S., Mascitti V., Lu P.P., Ishida H.: Synthesis 1959 (2002).
61. Clostre F.: Ann. Pharm. Fr. 57 (Suppl. 1), 1S8 (1999).
62. Middelton E., Kandaswami C., Theoharides T.C.: Pharm. Rev. 52, 673 (2000).
63. Flavonoids in Health and Disease, Rice-Evans C.A., Packer L., Eds., Marcel Dekker, New York 2003.
64. Flavonoids: Chemistry, Biochemistry and Applications, Andersen O.M., Markham K.R. Ed., CRC Press, Boca Raton 2006.
65. Křen V., Kubisch J., Sedmera P., et al.: J. Chem. Soc., Perkin Trans. 1, 2467 (1997).
66. Ross J.A., Kasum C.M.: Ann. Rev. Nutr. 22, 19 (2002).
67. Wu A.H., Wan P., Hankin J., Tseng C.C., Yu M. C., Pike M.C.: Carcinogenesis 23, 1491 (2002).
68. Meritt R.J., Jenks B.H.: J. Nutr. 134, 1220S (2004).
69. Harborne J.B., Williams C.A.: Phytochemistry 55, 481 (2000).
70. Birt D.F., Hendrich S., Wang W.: Pharmacol. Ther. 90, 157 (2001).
71. Dixon R.A., Ferreira D.: Phytochemistry 60, 205 (2002).
72. Stanosz S., Puk E., Grobelny W., Stanosz M., Kazikowska A.: Przegl. Menopauz. 3, 182 (2006).
73. Polkowski K., Popiolkiewicz J., Krzeczynski P., et al.: Cancer Lett. 203, 59 (2004).
74. Rusin A., Gogler A., Bochenek D., Glowala- Kosinska M., Grynkiewicz G., Krawczyk Z.: Cancer Mol. Pharmacol. submitted.
75. Lewis P.T., Kaltia S., Wähälä K.: J. Chem. Soc., Perkin Trans. 1. 2481 (1998).
76. Lewis P.T., Wähälä K.: Tetrahedron Lett. 39, 9559 (1998).
77. Boryski J., Grynkiewicz G.: Synthesis 2170 (2001).
78. Allevi P., Anastasia M., Ciuffreda P., Bigatti E., Macdonald P.: J. Org. Chem. 58, 4175 (1993).
79. Bender R.P., Jablonsky M.J., Shadid M., et al.: Biochemistry 47, 4501 (2008).
80. Wiczkowski W., Romaszko J., Bucinski A., Szawara-Nowak D., Honke J., Zielinski H., Piskula M.K.: J. Nutr. 138, 885 (2008).
81. Fernandez S.P., Wasowski C., Loscalzo L.M., Granger R.E., Johnston G.A.R., Paladini A.C., Marder M.: Eur. J. Pharmacol. 539, 168 (2006).
82. Harborne J.B., Williams C.A.: Nat. Prod. Rep. 15, 631 (1998).
83. Feizi T.: Curr. Opin. Struct. Biol. 3, 701 (1993).
84. Křen V.: in Glycoscience; Chemistry and Chemical Biology, B. Fraser-Reid, K. Tatsuka, J. Thiem, Eds., Vol 1, Chapter 9.3, p. 2471, Springer, Berlin 2001.
85. Larsen E., Kharazmi A., Christensen L.P., Christensen S.B.: J. Nat. Prod. 66, 994 (2003).
86. Natori N.; Koezuka Y., Higa T.: Tetrahedron Lett. 34, 5591 (1993).
87. Brutkiewicz R. R., Sriram V.: Crit. Rev. Oncol./Hematol. 41, 287 (2002).
88. Brutkiewicz R. R., Lin Y., Cho S., Hwang Y. K., Sriram V., Roberts T. J.: Crit. Rev. Immunol. 23, 403 (2003).
89. Zhou D., Cantu C., Sagiv Y., et al.: Science 303, 523 (2004).
90. Crul M., Mathor R.A.A., Giaccone G., et al.: Cancer Chemother. Pharmacol. 49, 287 (2002).
91. Wrotnowski C.: Genet. Eng. News 21, 1 (2001).
92. Mocchetti I.: Cell Mol. Life Sci. 62, 2283 (2005).
93. Mimee B., Labbe C., Pelletier R., Belanger R.R.: Antimicrob. Agents Chemother. 49, 1597 (2005).
94. Sihorkar V., Vyas S.P.: J. Pharm. Pharmaceut. Sci. 4, 138 (2001).
95. Sato T., Sunamoto J.: Prog. Lipid Res. 31, 345 (1992).
96. Ochi A., Shibata S., Mori K., Sato T., Sunamoto J.: Drug Deliv. Syst. 5, 261 (1990).
97. Antiviral Drug Development. A Multidisciplinary Approach, De Clercq E., Walker R.T. Eds., Plenum Press, New York & London 1988.
98. Antiviral chemotherapy, Jefferies D.J., De Clercq E. Ed., Wiley, Chichester 1995.
99. Boryski J.: in: Antiviral activity of nucleoside analogs and their application in therapy. Barciszewski J., Łastowski K., Koroniak H. Eds., New trends in molecular biology, genetic engineering and medicine (in Polish), Sorus, Poznaò 1996.
100. Schaeffer H.J., Beuchamp L., de Miranda P., Elion G.B, Bauer D.J., Collins P.: Nature 272, 583 (1978).
101. Elion G.B.: Am. J. Med., 73, 7 (1982).
102. Agrofolio L.A., Challand S.R.: in Acyclic, Carbocyclic and L-Nucleosides, Kluwer, Dordrecht, Boston, London 1998.
103. De Clercq E., Holy A., Rosenberg I., Sakuma T., Balzarini J., Maudgal P.C.: Nature 323, 464 (1986).
104. De Clercq E.: J. Med. Chem. 29, 1561 (1986).
105. Prusoff W.H.: Biochim. Biophys. Acta 32, 295 (1959).
106. Witkowski J.T., Robins R.K., Sidwell R.W., Simon L.N.: J. Med. Chem. 15, 1150 (1972).
107. Janeba Z., Balzarini J., Andrei G., Snoeck R., De Clercq E., Robins M.J.: J. Med. Chem. 48, 4690 (2005).
108. Malet-Martino M., Martino R.: Oncologist 7, 288 (2002).
109. Miles R.W., Tyler P.C., Furneaux R.H., Bagdassarian C.K., Schramm V.L.: Biochemistry 37, 8615 (1998).
110. Knapp S.: Chem. Rev. 95, 1859 (1995).
111. Garner P.: in Synthetic Approaches to Complex Nucleoside Antibiotics. Studies in Natural Product Chemistry, Atta-ur-Rahman Ed., Elsevier, Amsterdam 1988.
112. Reichstein T., Weiss E.: Angew. Chem. Int. Ed. 1, 572 (1962).
113. Oleszek W., Głowniak K., Leszczyński B. Eds., Biochemical environmental interactions (in Polish), p. 213, AM, Lublin 2001.
114. th ed., p. 289, WB Saunders, Edinburgh 2002.
115. Kubinyi H.: Arzneim. Forsch. 28, 493 (1978).
116. Geuns J.M.: Phytochemistry 64, 913 (2003).
117. Lei J., Li X., Gong X., Zheng Y.: Molecules 12, 2140 (2007).
118. Fahey J.W., Zalcmann A.T., Talalay P.: Phytochemistry 56, 5 (2001).
119. Mikuni T., Nakanishi K., Hara K., et al.: Biol. Pharm. Bull. 31, 1155 (2008).
120. Jimenez C., Riguera R.: Nat. Prod. Rep. 11, 591 (1994).
121. Stella V. J.: J. Med. Chem. 23, 1275 (1980).
122. Priebe W., Fokt I., Grynkiewicz G. in: Glycoscience Chemistry and Chemical Biology, Fraser-Reid B.O., Tatsuta K., Thiem J. Eds., Vol. 1, p. 699, Springer Verlag, Berlin 2008.
123. Lipinski C.A., Lombard F., Dominy B.W., Feeney P.J: Adv. Drug Deliv. Rev. 23, 3 (1997).
124. Thibodeaux C.J., Melancon C.E., Liu H.: Nature 446, 1008 (2007).