Synthesis, structural studies and biological properties of new TBA analogues containing an acyclic nucleotide

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8244-8253

  Coppola, Teresa ^a   Varra, Michela ^a   Oliviero, Giorgia ^a   Galeone, Aldo ^a   D'Isa, Giuliana ^a   Mayol, Luciano ^a   Morelli, Elena ^a   Bucci, Maria Rosaria ^a   Vellecco, Valentina ^a   Cirino, Giuseppe ^a   Borbone, Nicola ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Acyclic nucleoside phosphoramidite; CD quadruplex structures; TBA analogues; Thrombin inhibitor

Indexed keywords

ACYCLIC NUCLEOSIDE; APTAMER; N 1 (3 HYDROXY 2 HYDROXYMETHYL 2 METHYLPROPYL)THYMIDINE; NUCLEOTIDE DERIVATIVE; THROMBIN BINDING APTAMER DERIVATIVE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; DRUG ACTIVITY; DRUG EFFECT; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; PROTHROMBIN TIME; STRUCTURE ACTIVITY RELATION;

APTAMERS, NUCLEOTIDE; BLOOD COAGULATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; FIBRINOGEN; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEOTIDES; REFERENCE STANDARDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE; THROMBIN; TIME FACTORS;

EID: 50349084256     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.040     Document Type: Article

References (45)

1. Bode W. Blood Cell. Mol. Dis. 36 (2006) 122-130
2. Dahlback B. J. Int. Med. 257 (2005) 209-223
3. Colman R.W., Hirsh J., Marder V.J., and Clowes A.W. Hemostasis and Thrombosis: Basic Principles and Clinical Practice. 4th ed. (2004), Lippincott Williams and Wilkins, Philadelphia 17-20
4. Weitz J.I., and Hirsh J. Chest 119 (2001) 95S-107S
5. Di Nisio M., Middeldorp S., and Buller H.R. N. Engl. J. Med. 353 (2005) 1028-1040
6. Bock L.C., Griffin L.C., Latham J.A., Vermaas E.H., and Toole J.J. Nature 355 (1992) 564-566
7. Griffin L.C., Tidmarsh G.F., Bock L.C., Toole J.J., and Leung L.L.K. Blood 81 (1993) 3271-3276
8. Tsiang M., Gibbs C.S., Griffin L.C., Dunn K.E., and Leung L.L.K. J. Biol. Chem. 270 (1995) 19370-19376
9. Paborsky L.R., McCurdy S.N., Griffin L.C., Toole J.J., and Leung L.L.K. J. Biol. Chem. 268 (1993) 20808-20811
10. Tasset D.M., Kubik M.F., and Steiner W. J. Mol. Biol. 272 (1997) 688-698
11. Padmanabhan K., Padmanabhan K.P., Ferrara J.D., Sadler J.E., and Tulinsky A. J. Biol. Chem. 268 (1993) 17651-17654
12. Macaya R.F., Schultze P., Smith F.W., Roe J.A., and Feigon J. Proc. Natl. Acad. Sci. U.S.A 90 (1993) 3745-3749
13. Wang K.Y., McCurdy S., Shea R.G., Swaminathan S., and Bolton P.H. Biochemistry 32 (1993) 1899-1904
14. Wang K.Y., Krawczyk S.H., Bischofberger N., Swaminathan S., and Bolton P.H. Biochemistry 32 (1993) 11285-11292
15. Padmanabhan K., and Tulinsky A. Acta Crystallogr. D52 (1996) 272-282
16. Tuerk C., and Gold L. Science 249 (1990) 505-510
17. Abelson J. Science 249 (1990) 488-489
18. Nimjee S.M., Rusconi C.P., and Sullenger B.A. Annu. Rev. Med. 56 (2005) 555-583
19. Mao X., and Gmeiner W.H. Biophys. Chem. 113 (2005) 155-160
20. Kelly J.A., Feigon J., and Yeates T.O. J. Mol. Biol. 256 (1996) 417-422
21. Fialová M., Kypr J., and Vorlìcková M. Biochem. Biophys. Res. Commun. 344 (2006) 50-54
22. He G.-X., Krawczyk S.H., Swaminathan S., Shea R.G., Dougherty J.P., Terhorst T., Law V.S., Griffin L.C., Coutré S., and Bischofberger N. J. Med. Chem. 41 (1998) 2234-2242
23. He G.-X., Williams J.P., Postich M.J., Swaminathan S., Shea R.G., Terhorst T., Law V.S., Mao C.T., Sueoka C., Coutré S., and Bischofberger N. J. Med. Chem. 41 (1998) 4224-4231
24. Krawczyk S.H., Bischofberger N., Griffin L.C., Law V.S., Shea R.G., and Swaminathan S. Nucleosides Nucleotides Nucleic Acids 14 (1995) 1109-1116
25. Martino L., Virno A., Randazzo A., Virgilio A., Esposito V., Giancola C., Bucci M., Cirino G., and Mayol L. Nucleic Acids Res. 34 (2006) 6653-6662
26. Merle Y., Bonneil E., Merle L., Sage J., and Szmezö A. Int. J. Biol. Macromol. 17 (1995) 239-246
27. Marshalko S.J., Schweitzer I.B., and Beardsley G.P. Biochemistry 34 (1995) 9235-9248
28. Zhang L., Periz A., and Meggers E.V. J. Am. Chem. Soc. 127 (2005) 4174-4175
29. Joyce G.F. Nature 418 (2002) 214-221
30. Mitsunobu O. Synthesis 1 (1981) 1-28
31. Di Grandi M.J., and Tilley J.W. Tetrahedron Lett. 37 (1996) 4327-4330
32. Cruickshank K.A., Jiricny J., and Reese C.B. Tetrahedron Lett. 25 (1984) 681-684
33. Park K.H., Yoon Y.J., and Lee S.G. Tetrahedron Lett. 35 (1994) 9737-9740
34. Sinha N.D., Biernat J., McManus J., and Koster H. Nucleic Acids Res. 12 (1984) 4539-4557
35. Dapić V., Abdomerović V., Marrington R., Peberdy J., Rodger A., Trent J.O., and Bates P.J. Nucleic Acids Res. 31 (2003) 2097-2107
36. Mergny J.-L., Phan A.-T., and Lacroix L. FEBS Lett. 435 (1998) 74-78
37. Mergny J.-L., Li J., Lacroix L., Amrane S., and Chaires J.B. Nucleic Acids Res. 33 (2005) e138/1-e138/6
38. Saccà B., Lacroix L., and Mergny J.-L. Nucleic Acids Res. 33 (2005) 1182-1192
39. Gros J., Rosu F., Amrane S., De Cian A., Gabelica V., Lacroix L., and Mergny J.-L. Nucleic Acids Res. 35 (2007) 3064-3075
40. Baldrich E., and O'Sullivan C.K. Anal. Biochem. 341 (2005) 194-197
41. Nagatoishi S., Tanaka Y., and Tsumoto K. Biochem. Biophys. Res. Commun. 352 (2007) 812-817
42. Kretz C.A., Stafford A.R., Fredenburgh J.C., and Weitz J. J. Biol. Chem. 281 (2006) 37447-37485
43. Hwang T.L., and Shaha A.J. J. Magn. Res. A112 (1995) 275-279
44. Dalvit C. J. Biomol. NMR 11 (1998) 437-444
45. Gray D.M., Hung S.-H., and Johnson K.H. Methods Enzymol. 246 (1995) 19-34