Synthesis and Bioactivity of Carbohydrate Derivatives of Indigo, Its Isomers and Heteroanalogues

ChemMedChem

Volumn 6, Issue 1, 2011, Pages 25-37

  Karapetyan, Gnuni ^a   Chakrabarty, Kuheli ^a   Hein, Martin ^a   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Antitumor agents; Enzyme inhibitors; Glycosides; Indigo; Indirubin

Indexed keywords

AKASHIN A; ANTINEOPLASTIC AGENT; CARBOHYDRATE; GALACTOSE; GLYCOSIDE; INDIGO; INDIRUBIN; INDIRUBIN 3 MONOXIM; INDIRUBIN N RHAMNOSIDE; ISOINDIGO; MANNOSE; N (BETA LEVO RHAMNOPYRANOSYL)INDIRUBIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CANCER CELL CULTURE; DEPROTECTION REACTION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HUMAN; HUMAN CELL; IC 50; ISOMER; PRIORITY JOURNAL; REVIEW; SUBSTITUTION REACTION;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; FEMALE; GLYCOSIDES; GLYCOSYLATION; HUMANS; INDOLES; ISOMERISM; MALE; MICE; NEOPLASMS;

EID: 78650577464     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000374     Document Type: Review

References (91)

1. Z. Q. Xia, M. H. Zenk, Phytochemistry 1992, 31, 2695-2697;
2. H. Schweppe, Handbuch der Naturfarben, Ecomed, Landsberg/Lech, 1993, 282-318.
3. P. G. Miles, H. Lund, J. R. Raper, Arch. Biochem. Biophys. 1956, 62, 1-5;
4. T. Hosoe, K. Nozawa, N. Kawahara, K. Fukushima, K. Nishimura, M. Miyaji, K. Kawai, Mycopathologia 1999, 146, 9-12;
5. H. Falanghe, P. A. Bobbio, Arch. Biochem. Biophys. 1962, 96, 430-433;
6. H. Laatsch, H. Ludwig-Koehn, Liebigs Ann. Chem. 1986, 1847-1853.
7. P. Friedlaender, Justus Liebigs Ann. Chem. 1907, 351, 390-420.
8. P. J. Scheuer, T. Higa, Heterocycles 1976, 4, 227-230.
9. R. P. Maskey, I. Grün-Wollny, H. H. Fiebig, H. Laatsch, Angew. Chem. 2002, 114, 623-625; Angew. Chem. Int. Ed. 2002, 41, 597-599;
10. R. P. Maskey, I. Grün-Wollny, H. Laatsch, Nat. Prod. Res. 2005, 19, 137-142.
11. Indirubin, the Red Shade of Indigo (Eds.: L. Meijer, N. Guyard, L.-A. Skaltsounis, G. Eisenbrand), Station Biologique, Roscoff, 2006.
12. Z. Xiao, Y. Hao, B. Liu, L. Qian, Leuk. Lymphoma 2002, 43, 1763-1768;
13. K. Iwaki, M. Kurimoto, Recent Res. Dev. Cancer 2002, 4, 429-437.
14. A. Beauchard, Y. Ferandin, S. Frere, O. Lozach, M. Blairvacq, L. Meijer, V. Thiery, T. T. Besson, Bioorg. Med. Chem. 2006, 14, 6434-6443.
15. J. W. Lee, M. J. Moon, H. Y. Min, H. J. Chung, E. J. Park, H. J. Park, J. Y. Hong, Y. C. Kim, S. K. Lee, Bioorg. Med. Chem. Lett. 2005, 15, 3948-3952;
16. M. J. Moon, S. K. Lee, J.-W. Lee, W. K. Song, S. W. Kim, J. I. Kim, C. Cho, S. J. Choi, Y.-C. Kim, Bioorg. Med. Chem. 2006, 14, 237-246;
17. R. Jautelat, T. Brumby, M. Schaefer, H. Briem, G. Eisenbrand, S. Schwahn, M. Krueger, U. Luecking, O. Prien, G. Siemeister, ChemBioChem 2005, 6, 531-540;
18. R. Jautelat, T. Brumby, O. Prien, M. Schaefer, G. Siemeister, WO 2002100401, 2002 [Chem. Abstr., 2003, 138, 39-142];
19. T. Matsuda, Farumashia 2006, 42, 705-708.
20. T. Hunter, Cell 1995, 80, 225-236.
21. P. Cohen, Nat. Rev. Drug Discovery 2002, 1, 309-315;
22. M. E. Noble, J. A. Endicott, L. N. Johnson, Science 2004, 303, 1800-1805.
23. M. Malumbres, M. Barbacid, Trends Biochem. Sci. 2005, 30, 630-641;
24. M. Knockaert, P. Greengard, L. Meijer, Trends Pharmacol. Sci. 2002, 23, 417-425;
25. G. I. Shapiro, J. Clin. Oncol. 2006, 24, 1770-1783;
26. Inhibitors of Cyclin-Dependent Kinases as Antitumor Agents (Eds.: P.-J. Smith, E.-W. Yue), CRC Press, Taylor & Francis, Boca Raton, 2007.
27. L. Meijer, M. Flajolet, P. Greengard, Trends Pharmacol. Sci. 2004, 25, 471-480.
28. E. Xingi, D. Smirlis, V. Myrianthopoulos, P. Magiatis, K. M. Grant, L. Meijer, E. Mikros, A. L. Skaltsounis, K. Soteriadou, Int. J. Parasitology 2009, 39, 1289-1303.
29. S. Leclerc, M. Garnier, R. Hössel, D. Marko, J. A. Bibb, G. L. Snyder, P. Greengard, J. Biernat, E.-M. Mandelkow, G. Eisenbrand, L. Meijer, J. Biol. Chem. 2001, 276, 251-260;
30. M. Knockaert, M. Blondel, S. Bach, M. Leost, C. Elbi, G. Hager, S. R. Naggy, D. Han, M. Denison, M. French, X. P. Ryan, P. Magiatis, P. Polychronopoulos, P. Greengard, L. Skaltsounis, L. Meijer, Oncogene 2004, 23, 4400-4412.
31. C. J. Cooksey, Molecules 2001, 6, 736-739.
32. L. Meijer, A.-L. Skaltsounis, P. Magiatis, P. Polychronopoulos, M. Knockaert, M. Leost, X. P. Ryan, A. C. Vonica, A. Brivanlou, R. Dajani, A. Crovace, C. Tarricone, A. Musacchio, S. M. Roe, L. Pearl, P. Greengard, Chem. Biol. 2003, 10, 1255-1266;
33. P. Polychronopoulos, P. Magiatis, A. L. Skaltsounis, V. Myrianthopoulos, E. Mikros, A. Tarricone, A. Musacchio, S. M. Roe, L. Pearl, M. Leost, P. Greengard, L. Meijer, J. Med. Chem. 2004, 47, 935-946.
34. A. Beauchard, H. Laborie, H. Rouillard, O. Lozach, Y. Ferandin, R. L. Guevel, C. G. Guillouzo, L. Meijer, T. Besson, V. Thiery, Bioorg. Med. Chem. 2009, 17, 6257-6263.
35. L. Meijer, R. Hössel, S. Leclerc, J. A. Endicott, M. E. M. Nobel, A. Lawrie, P. Tunnah, M. Loest, E. Damiens, D. Marie, D. Marko, E. Niederberger, W. Thang, G. Eisenbrand, Nat. Cell Biol. 1999, 1, 60-67.
36. For a review, see: G. Eisenbrand, F. Hippe, S. Jakobs, A. Muehlbeyer, J. Cancer Res. Clin. Oncol. 2004, 130, 627-635.
37. X. J. Ji, F. R. Zhang, Acta Pharm. Sin. 1985, 20, 137-139.
38. T. G. Davies, P. Tunnah, L. Meijer, D. Marko, G. Eisenbrand, J. A. Endicott, M. Noble, Structure 2001, 9, 389-397.
39. C. Li, Y. Go, Z. Mao, K. Koyano, Y. Kay, N. Kanehisha, Q. Zhu, Z. Zhou, S. Wu, Bull. Chem. Soc. Jpn. 1996, 69, 1621-1627.
40. S. H. Kim, S. J. Choi, Y. C. Kim, H. J. Kuh, Arch. Pharmacal Res. 2009, 32, 915-922.
41. D. Marko, S. Schätzle, A. Friedel, A. Genzlinger, H. Zankl, G. Eisenbrand, British J. Cancer 2001, 84, 283-289.
42. G. Eisenbrand, WO 200061555, 2000 [Chem. Abstr., 2000, 133, 296-321].
43. S. Libnow, K. Methling, M. Hein, D. Michalik, M. Harms, K. Wende, A. Flemming, M. Koeckerling, H. Reinke, P. J. Bednarski, M. Lalk, P. Langer, Bioorg. Med. Chem. 2008, 16, 5570-5583.
44. L. Wang, X. Liu, R. Chen, US 6566341, 2003 [Chem. Abstr. 2003, 138, 379-213];
45. L. Wang, X. Liu, R. Chen, WO 2003051900, 2003 [Chem. Abstr. 2003, 139, 47-135].
46. G. W. Gribble, S. J. Berthel in Studies in Natural Products Chemistry, Vol. 12, Elsevier Science, New York, 1993, pp.-365-409; Isolation of staurosporine.
47. S. Omura, Y. Iwai, A. Hirano, A. Nakagawa, J. Awaya, H. Tsuchiya, Y. Takahashi, R. Masuma, J. Antibiot. 1977, 30, 275-282; Synthesis.
48. J. T. Link, S. Raghavan, M. Gallant, S. J. Danishefsky, T. C. Chou, L. M. Ballas, J. Am. Chem. Soc. 1996, 118, 2825-2842; Pharmacological activity.
49. Y. Yamashita, N. Fujii, C. Murakata, T. Ashizawa, M. Okabe, H. Nakano, Biochemistry 1992, 31, 12069-12075.
50. M. Hein, D. Michalik, P. Langer, Synthesis 2005, 3531-3534;
51. M. Hein, T. B. P. Nguyen, D. Michalik, H. Görls, M. Lalk, P. Langer, Tetrahedron Lett. 2006, 47, 5741-5745.
52. J. D. Chisholm, D. L. Van-Vranken, J. Org. Chem. 1995, 60, 6672-6673;
53. E. J. Gilbert, D. L. Van-Vranken, J. Am. Chem. Soc. 1996, 118, 5500-5501.
54. J.-B. Meng, P. Li, Y.-Z. He, L.-L. Xu, Y.-M. Wang, Gaodeng Xuexiao Huaxue Xuebao 2001, 22, 63-65; [Chem. Abstr. 2002, 137, 179-362].
55. B. Li, B. Yu, Y. Hui, M. Li, X. Han, K.-P. Fung, Carbohydr. Res. 2001, 331, 1-7.
56. L. Kalb, Ber. Dtsch. Chem. Ges. 1909, 42, 3642-3652.
57. S. Libnow, M. Hein, D. Michalik, P. Langer, Tetrahedron Lett. 2006, 47, 6907-6909.
58. C. Chavis, C. De-Gourcy, F. Dumont, J.-L. Imbach, Carbohydr. Res. 1983, 113, 1-20;
59. J. G. Douglas, J. Honeyman, J. Chem. Soc. 1955, 3674-3680;
60. M. N. Preobrazhenskaya, I. V. Yartseva, L. V. Ektova, Nucleic Acid Chem. 1978, 2, 725-727;
61. I. V. Yartseva, L. V. Ektova, M. N. Preobrazhenskaya, Bioorg. Khim. 1975, 1, 189-194.
62. S. J. Holt, P. W. Sadler, Proc. R. Soc. (London) 1958, 148B, 481-494;
63. J. C. Rodriguez-Dominguez, A. Balbuzano-Deus, M. A. Lopez-Lopez, G. Kirsch, J. Heterocycl. Chem. 2007, 44, 273-275.
64. P. Langer, S. Libnow, M. Hein, Synlett 2009, 221-224.
65. J. E. Pretka, H. G. Lindwall, J. Org. Chem. 1954, 19, 1080-1088.
66. M. Sassatelli, E. Saab, F. Anizon, M. Prudhomme, P. Moreau, Tetrahedron Lett. 2004, 45, 4827-4830;
67. M. Sassatelli, F. Bouchikhi, S. Messaoudi, F. Anizon, E. Debiton, C. Barthomeuf, M. Prudhomme, P. Moreau, Eur. J. Med. Chem. 2006, 41, 88-100;
68. M. Sassatelli, F. Bouchikhi, B. Aboab, F. Anizon, F. Doriano, M. Prudhomme, P. Moreau, Anti-Cancer Drugs 2007, 18, 1069-1074.
69. S. Messaoudi, M. Sancelme, V. Polard-Housset, B. Aboab, P. Moreau, M. Prudhomme, Eur. J. Med. Chem. 2004, 39, 453-458.
70. C. Papageorgiou, X. Borer, Helv. Chim. Acta 1988, 71, 1079-1083.
71. F. Bouchikhi, F. Anizon, P. Moreau, Eur. J. Med. Chem. 2008, 43, 755-762;
72. F. Bouchikhi, F. Anizon, P. Moreau, Eur. J. Med. Chem. 2009, 44, 2705-2710.
73. A. Echalier, K. Bettayeb, Y. Ferandin, O. Lozach, M. Clement, A. Valette, F. Liger, B. Marquet, J. C. Morris, J. A. Endicott, B. Joseph, L. Meijer, J. Med. Chem. 2008, 51, 737-751.
74. Q. Yao, C. Wang, J. Cheng, W. Hua, CN 101074229, 2007 [Chem. Abstr., 2008, 148, 78-880].
75. S. Libnow, PhD Thesis, Universität Rostock, 2008.
76. M. Kunz, K. M. Driller, M. Hein, S. Libnow, I. Hohensee, R. Ramer, B. Hinz, A. Berger, J. Eberle, P. Langer, ChemMedChem 2010, 5, 534-539.
77. A. J. Miller, M. C. Mihm, -Jr., New Engl. J. Med. 2006, 355, 51-65.
78. Y. Chudnovsky, P. A. Khavari, A. E. Adams, J. Clin. Invest. 2005, 115, 813-824.
79. S. Libnow, M. Hein, P. Langer, Tetrahedron Lett. 2008, 49, 289-291.
80. Similar conditions were used for the aldol condensation of thiazolidinones with isatins: H. Altuntas, O. Ates, B. S. Uydes-Dogan, F. I. Alp, D. Kaleli, O. Oezdemir, S. Birteksoez, G. Oetuek, D. Satana, M. Uzun, Arzneim. Forsch. 2006, 56, 239-248.
81. G. A. Russell, G. Kaupp, J. Am. Chem. Soc. 1969, 91, 3851-3859.
82. R. Miethchen, V. Fehring, Liebigs Ann. Recl. 1997, 553-561.
83. H. Paulsen, Angew. Chem. 1982, 94, 184-201; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-173.
84. L. Hough, K. C. McCarthy, A. C. Richardson, Recl. Trav. Chim. Pays-Bas 1991, 110, 450-458.
85. S. Nam, R. Buettner, J. Turkson, D. Kim, J. Q. Cheng, S. Muehlbeyer, F. Hippe, S. Vatter, K. H. Merz, G. Eisenbrand, R. Jove, Proc. Natl. Acad. Sci. USA 2005, 102, 5998-6003.
86. O. Prien, A. Steinmeyer, G. Siemeister, R. Jautelat, WO 200234717, 2002 [Chem. Abstr., 2002, 136, 340-538].
87. S. Jakobs, PhD Thesis, Universität Kaiserslautern, 2002.
88. S. Jakobs, K. H. Merz, S. Vatter, G. Eisenbrand, Int. J. Clin. Pharmacol. Ther. 2005, 43, 592-594.
89. S. Mühlbeyer, PhD Thesis, Universität Kaiserslautern, 2007.
90. G. Eisenbrand, F. Hippe, WO 2003070703, 2003 [Chem. Abstr., 2003, 139, 197-710].
91. E. Wille, W. Lüttke, Chem. Ber. 1973, 106, 3240-3257.