Polyphosphates and Pyrophosphates of Hexopyranoses as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Effect on Oxygen Release

ChemMedChem

Volumn 6, Issue 1, 2011, Pages 153-168

  Fylaktakidou, Konstantina C ^a,b   Duarte, Carolina D ^a,c,d   Koumbis, Alexandros E ^a,e   Nicolau, Claude ^a,c,f   Lehn, Jean Marie ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b DEMOCRITUS UNIVERSITY OF THRACE   (Greece)

^c NormOxys Inc   (United States)

^d IQVIA   (United States)

^e ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^f TUFTS UNIVERSITY   (United States)

Author keywords

Allosteric effectors; Hemoglobin; Oxygen release; Phosphorylated carbohydrates; Structure activity relationships

Indexed keywords

1 O METHYL ALPHA GLUCOSE 2,3,4 TRIPHOSPHATE; 1 O METHYL ALPHA GLUCOSE BISPYROPHOSPHATE; 1 O METHYL ALPHA GLUCOSE TETRAKISPHOSPHATE; 1 O METHYL ALPHA MANNOSE 2,3,4 TRISPHOSPHATE; 1 O METHYL ALPHA MANNOSE TETRAKISPHOSPHATE; ALPHA GALACTOSE 1,2,3,4 TETRAKISPHOSPHATE; ALPHA GALACTOSE PENTAKISPHOSPHATE; ALPHA GLUCOSE 1,2,3,4 TETRAKISPHOSPHATE; ALPHA GLUCOSE PENTAKISPHOSPHATE; ALPHA MANNOSE 1,2,3,4 TETRAKISPHOSPHATE; ALPHA MANNOSE PENTAKISPHOSPHATE; BETA GALACTOSE 1,2,3,4 TETRAKISPHOSPHATE; BETA GLUCOSE 1,2,3,4 TETRAKISPHOSPHATE; BETA MANNOSE 1,2,3,4 TETRAKISPHOSPHATE; CARBOHYDRATE; DISACCHARIDE; GALACTOSE; GLUCOSE; HEMOGLOBIN; LACTOSE OCTAKISPHOSPHATE; MANNOSE; MONOSACCHARIDE; MYO INOSITOL HEXAKISPHOSPHATE; OXYGEN; PENTASODIUM 1,2,3,4,6 (ALPHA DEXTRO GLUCOPYRANOSYL) PENTAKISPHOSPHATE; PHOSPHATE; SUCROSE OCTAKISPHOSPHATE; SUGAR; TETRASODIUM 2,3,4,6 (1 O METHYL ALPHA DEXTRO MANNOPYRANOSYL) TETRAKISPHOSPHATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AFFINITY CHROMATOGRAPHY; ALLOSTERISM; ARTICLE; BINDING AFFINITY; DISSOCIATION CONSTANT; DRUG SYNTHESIS; HYDROGENATION; OXYGEN SATURATION; PHOSPHORYLATION; PRIORITY JOURNAL; SILYLATION; STRUCTURE ACTIVITY RELATION;

ALLOSTERIC REGULATION; ANOXIA; BINDING, COMPETITIVE; DIPHOSPHATES; DISACCHARIDES; HEMOGLOBINS; HUMANS; KINETICS; MONOSACCHARIDES; OXYGEN; PHYTIC ACID; POLYPHOSPHATES; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 78650572337     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000366     Document Type: Article

References (69)

1. R. Benesch, R. E. Benesch, Biochem. Biophys. Res. Commun. 1967, 26, 162-167;
2. R. Benesch, R. E. Benesch, C. I. Yu, Proc. Natl. Acad. Sci. USA 1968, 59, 526-532;
3. R. Benesch R. E. Benesch, Nature 1969, 221, 618-622.
4. A. Arnone, Nature 1972, 237, 146-149;
5. R. E. Benesch, R. Benesch, R. Renthal, W. B. Gratzer, Nature New Biol. 1971, 234, 174-176.
6. R. E. Benesch, R. Edalji, R. Benesch, Biochemistry 1977, 16, 2594-2597;
7. A. Arnone, M. F. Perutz, Nature 1974, 249, 34-36.
8. B. Teisseire, C. Ropars, M. O. Vallez, R. A. Herigault, C. Nicolau, J. Appl. Physiol. 1985, 58, 1810-1817.
9. K. C. Fylaktakidou, J.-M. Lehn, R. Greferath, C. Nicolau, Bioorg. Med. Chem. Lett. 2005, 15, 1605-1608.
10. C. Nicolau, R. Greferath, J.-M. Lehn, K. C. Fylaktakidou, Patent US 2006258626, 2006, [Chem. Abstr. 2006, 145, 483 718];
11. C. Kieda, R. Greferath, C. Crola da-Silva, K. C. Fylaktakidou, J.-M. Lehn, C. Nicolau, Proc. Natl. Acad. Sci. USA 2006, 103, 15576-15581;
12. G. Sihn, T. Walter, J.-C. Klein, I. Queguiner, H. Iwao, C. Nicolau, J.-M. Lehn, P. Corvol, J.-M. Gasc, FEBS Lett. 2007, 581, 962-966;
13. C. Nicolau, J.-M. Lehn, L'Arbre Vasculaire 2009, n°5, 24-25.
14. A. Biolo, R. Greferath, D. A. Siwik, F. Qin, E. Valsky, K. C. Fylaktakidou, S. Pothukanuri, C. D. Duarte, R. P. Schwarz, J.-M. Lehn, C. Nicolau, W. S. Colucci, Proc. Natl. Acad. Sci. USA 2009, 106, 1926-1929.
15. D. L. Currell, H. Goldwhite, S. Lim, N. Patel, Phosphorus Sulfur Silicon Relat. Elem. 1990, 51/52, 35-38.
16. M. Martin Lomas, J.-M. Mato de La Paz (Europharma SA), ES 2019839, 1991, [Chem. Abstr. 1992, 117, 49 136];
17. H. N. Caro, M. Martin-Lomas, M. Bernabe, Carbohydr. Res. 1993, 240, 119-131.
18. T. Usui, T. Igami, T. Kakigami, H. Hamashima, T. Jomori, A. Tashita, Y. Ishiwatari, S. Yokochi, T. Mitani, Y. Suzuki, A. Hasegawa, (Sanwa Kagaku Kenkyusho Co., Ltd.), EP0771815, 1997, [Chem. Abstr. 1997, 127, 17 911];
19. T. Ikami, N. Tsuruta, H. Inagaki, T. Kakigami, Y. Matsumoto, N. Tomiya, T. Jomori, T. Usui, Y. Suzuki, H. Tanaka, D. Miyamoto, H. Ishida, A. Hasegawa, M. Kiso, Chem. Pharm. Bull. 1998, 46, 797-806.
20. D. Mamelak, M. Mylvaganam, E. Tanahashi, H. Ito, H. Ishida, M. Kiso, C. Lingwood, Carbohydr. Res. 2001, 335, 91-100.
21. M. Siren, (Bioneris AB), WO 2004022123, 2004, [Chem. Abstr. 2004, 140, 259 175].
22. A. G. Roth, S. Redmer, C. Arenz, Bioorg. Med. Chem. 2010, 18, 939-944.
23. P. Camilleri, R. F. Jones, A. J. Kirby, R. Stroemberg, J. Chem. Soc. Perkin Trans. 2 1994, 10, 2085-2090;
24. A. J. Kirby, R. Stroemberg, J. Chem. Soc. Chem. Commun. 1994, 709-710.
25. J. E. M. Basten, C. A. A. Van-Boeckel, R. C. Buijsman, C. M. Dreef-Tromp, (Akzo Nobel NV, Univ. Leiden), WO 9965934, 1999, [Chem. Abstr. 2000, 132, 36 036];
26. R. C. Buijsman, J. E. M. Basten, C. M. Dreef-Tromp, G. A. van der Marel, C. A. A. van-Boeckel, J. H. van-Boom, Bioorg. Med. Chem. 1999, 7, 1881-1890.
27. N. P. Zakurdaeva, E. D. Derzhavina, V. V. Andreyanov, V. N. Kryazhev, (Vgni i Pi Chimiko Photografi), SU 1420592, 1988, [Chem. Abstr. 1989, 110, 104 842];
28. G. Faraone, A. Giorgetti, F. Weickmann, DE 1302 721, 1971, [Chem. Abstr. 1971, 75, 78 367];
29. G. Faraone, A. Giorgetti, (Ferrania SPA), GB 957 132, 1964 [Chem. Abstr. 1964, 61, 26 236];
30. G. Faraone, A. Giorgetti, (Ferrania SPA), IT 630 656, 1961, [Chem. Abstr. 1963, 58, 9043];
31. G. H. Harris, R. S. Olson, R. D. Wilcox, (Dow Chemical Co.), US 3652 743, 1972, [Chem. Abstr. 1972, 76, 139 922].
32. M. Malmberg, N. Rehnberg, Tetrahedron Lett. 1995, 36, 8879-8880.
33. M. Siren, (Perstorp AB), WO 9749 408, 1997, [Chem. Abstr. 1998, 128, 123 820];
34. L. Persson, N. Rehnberg, (Perstorp AB), WO 9609 310, 1996, [Chem. Abstr. 1996, 125, 115 065].
35. C. M. H. Hensgens, H. Santos, C. Zhang, W. H. Kruizinga, T. A. Hansen, Eur. J. Biochem. 1996, 242, 327-331.
36. J. N. S. Evans, C. J. Tolman, S. Kanodia, M. F. Roberts, Biochemistry 1985, 24, 5693-5698;
37. A. Lehmacher, A. B. Vogt, R. Hensel, FEBS Lett. 1990, 272, 94-98.
38. J. C. Su, W. Z. Hassid, J. Biol. Chem. 1960, 235, PC36-PC37;
39. H. N. Wood, D. G. Lynn, Differentiation 1981, 18, 51-53;
40. C.-C. Su, W. Z. Hassid, Biochemistry 1962, 1, 474-480.
41. A. Galione, Science 1993, 259, 325-326;
42. A.-H. Tashjian, -Jr., D. Zhao, J. Yang, K.-E. Jones, C. Gerald, C. Gerald, P. Hogan, W.-W. Chin, H. Koshiyama, Y. Tanaka, International Congress Series (1992), 1003 (Calcium Regulating Hormones and Bone Metabolism, Vol.-11), 102-104.
43. G. Zhang, E. G. Teggatz, A. Y. Zhang, M. J. Koeberl, F. Li, L. Chen, P.-L. Li, Am. J. Physiol. Heart Circ Physiol. 2005, 290, H1172-H1181;
44. D. A. Deshpande, T. A. White, S. Dogan, T. F. Walseth, P. A. Panettieri, M. S. Kannan, Am. J. Physiol. 2005, 288, L773-L788;
45. H. Koshiyama, H. C. Lee, A. H. Tashjian, -Jr., J. Biol. Chem. 1991, 266, 16985-16988.
46. E. Abel-Santos, T. Dodatko, New J. Chem. 2007, 31, 748-755.
47. R. P. Newton, N. A. Hakeem, B. J. Salvage, G. Wassenaar, E. E. Kingston, Rapid Commun. Mass Spectrom. 1988, 2, 118-126;
48. R. P. Newton, E. E. Kingston, B. J. Salvage, J. H. Beynon, N. A. Hakeem, G. Wassenaar, Biochem. Soc. Trans. 1986, 14, 964-965.
49. A. Hoshi, F. Kanzawa, K. Kuretani, T. Kanai, K. Kikugawa, M. Ichino, Gann 1973, 64, 519-522.
50. R. P. Newton, E. E. Kingston, A. Overton, Rapid Commun. Mass Spectrom. 1995, 9, 305-311.
51. P. Besada, D. H. Shin, S. Costanzi, H. Ko, C. Mathe, J. Gagneron, G. Gosselin, S. Maddileti, T. K. Harden, K. A. Jacobson, J. Med. Chem. 2006, 49, 5532-5543;
52. E. Nandanan, E. Camaioni, S.-Y. Jang, Y.-C. Kim, G. Cristalli, P. Herdewijn, J. A. Secrist -III, K. N. Tiwari, A. Mohanram, T. K. Harden, J. L. Boyer, K. A. Jacobson, J. Med. Chem. 1999, 42, 1625-1638.
53. S. G. Brown, B. F. King, Y.-C. Kim, S. Y. Jang, G. Burnstock, K. A. Jacobson, Drug Dev. Res. 2000, 49, 253-259.
54. S. N. Lam, J. Gervay-Hague, Carbohydr. Res. 2002, 337, 1953-1965.
55. R. T. Brown, S. P. Mayalarp, J. Watts, J. Chem. Soc. Perkin Trans. 1 1997, 1633-1638.
56. R. R. Schmidt, W. Klotz, Synlett 1991, 168-170.
57. A. Boto, D. Hernández, R. Hernández, E. Suárez, J. Org. Chem. 2006, 71, 1938-1948.
58. M. M. Sim, H. Kondo, C.-H. Wong, J. Am. Chem. Soc. 1993, 115, 2260-2267;
59. M. M. Vaghefi, R. J. Bernacki, W. J. Hennen, R. K. Robins, J. Med. Chem. 1987, 30, 1391-1399;
60. M. P. Huestis, G. A. Aish, J. P. M. Hui, E. C. Soo, D. L. Jakeman, Org. Biomol. Chem. 2008, 6, 477-484;
61. J. V. O'Connor, H. A. Nunez, R. Barker, Biochemistry 1979, 18, 500-507.
62. S. J. Angyal, Angew. Chem. 1969, 81, 172-182; Angew. Chem. Int. Ed. Engl. 1969, 8, 157-166.
63. A. Zamyatina, S. Gronow, M. Puchberger, A. Graziani, A. Hofinger, P. Kosma, Carbohydr. Res. 2003, 338, 2571-2589.
64. K. Bock, C. Pedersen, Adv. Carbohydr. Chem. Biochem. 1983, 41, 27-66.
65. L. F. Johnson, M. E. Tate, Can. J. Chem. 1969, 47, 63-73.
66. L. Dee Nord, N. Kent Dalley, P. A. McKeman, R. K. Robins, J. Med. Chem. 1987, 30, 1044-1054.
67. A related behavior has been observed in the case of myo-inositol trispyrophosphate; S. Pothukanuri, J.-M. Lehn, unpublished results.
68. R. Benesch, R. Edalji, R. E. Benesch, Biochemistry 1976, 15, 3396-3398.
69. A. Riggs, Methods Enzymol. 1981, 76, 5-29.