Crystal and molecular structure of 5-trifluorothymine, a metabolite from human urine: Role of fluorine in stacking and hydrogen bonded interactions

Journal of Fluorine Chemistry

Volumn 129, Issue 6, 2008, Pages 493-497

  Rajeswaran, Manju ^a   Srikrishnan, Thamarapu ^b  

^a EASTMAN KODAK COMPANY   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

Dimeric hydrogen bonding of nucleic acid bases; Polyflourinated thymines; Stacking of fluorinated bases

Indexed keywords

EID: 44649191738     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.03.003     Document Type: Article

References (42)

1. Dunn D.B., Smith J.D., Zamenhof S., and Griboff G. Nature 174 (1954) 305-306
2. Zamenhof S., Griboff G., and Marullo N. Biochim. Biophys. Acta 13 (1954) 459-470
3. Soni S.D., Srikrishnan T., and Alderfer J.L. Nucleosides Nucleotides 15 (1996) 1945-1957
4. Soni S.D., and Srikrishnan T. Nucleosides Nucleotides Nucleic Acids 23 (2004) 1779-1795
5. Blokhina N.G., Vozny E.K., and Garin A.M. Cancer 30 (1972) 390-392
6. Karev N.I., Blokhina N.G., Vozhy E.K., and Pershin M.P. Neoplasma 19 (1972) 347-350
7. Valdidieso N., Bodey G.P., Gottlieb J.A., and Freirich E.J. Cancer Res. 36 (1976) 1821-1824
8. Cohen A.M. Drug Metab. Dispos. 3 (1975) 303-308
9. Fujimoto S., Akao T., Itoh B., Koshizuka I., Koyano K., Kitusakawa Y., Takahashi M., Minami T., Ishigami H., Nomura Y., and Itoh K. Cancer Res. 36 (1976) 33-36
10. Smolyanaskaya A.Z., and Tugarinov O.A. Neoplasma 19 (1972) 341-345
11. Stokes D.M., Paul B., Alderfer J.L., Wollman R.M., and Srikrishnan T. Nucleosides Nucleotides Nucleic Acids 21 (2002) 863-890
12. Tandon M., Kumar P., Wiebe G., and Wiebe L.I. Biochem. Pharm. 44 (1992) 2223-2228
13. Gupta O.D., Twamley B., Kirchmeier R.L., and Shreeve J.M. J. Flourine Chem. 106 (2000) 199-204
14. Chheda G.B. In: Fasman G. (Ed). Handbook of Biochemistry. 3rd ed. vol. 1 (1975), Chemical Rubber Company, Cleveland, OH 251-270
15. Chheda G.B., Dutta S.P., Mittleman A., Montgomery J.A., Sethi S.K., McCloskey J.A., and Patrzyc H.B. Cancer Res. 45 (1985) 5958-5963
16. Pendyala L., Cowens J.W., Chheda G.B., Dutta S.P., and Creaven P.J. Cancer Res. 48 (1988) 3533-3536
17. Heldman D., Graver M.R., Speicher C.F., and Twewyn R.W. J. Lab. Clin. Med. 101 (1983) 783-792
18. Tomey D.C., Waakas T.P., Altmann D., Gehrke C.W., and Zumalt R.W. J. Snyder. Cancer 35 (1975) 1095-1100
19. Dutta S.P., Grossberg A., Bhargava A.K., and Chheda G.B. Anticancer Res. 6 (1986) 135-138
20. Parthasarathy R., Ohrt J.M., and Chheda G.B. Biochemistry 16 (1977) 4999-5008
21. Arakali A.V., McCloskey J., Parthasarathy R., Alderfer J.L., and Chheda G.B. Nucleosides Nucleotides Nucleic Acids 16 (1997) 2193-2218
22. Srikrishnan T., Parthasarathy R., Pfleiderer W., De N.C., and Chheda G.B. Nucleosides Nucleotides 16 (1997) 239-255
23. Srikrishnan T., Parthasarathy R., Alderfer J.L., Dutta S.P., and Chheda G.B. Nucleosides Nucleotides 7 (1988) 45-60
24. Srikrishnan T., Parthasarathy R., De N.C., and Chheda G.B. Acta Cryst. C39 (1983) 1441-1445
25. Heldelberger C., Bohar J., and Kampschroer B. Cancer Res. 25 (1965) 377-381
26. Heidelberger C., Parsons D.G., and Remy D.C. J. Med. Chem. 7 (1964) 1-5
27. Ozeki K., Sakabe N., and Tanaka J. Acta Cryst. B25 (1969) 1038-1045
28. Portoalone G., Bencivenni L., Colapietro M., Pieretti A., and Ramondo F. Acta Chem. Scand. 53 (1999) 57-59
29. Twamley B., Gupta O.D., and Shreeve J.M. Acta Cryst. E58 (2002) o1040-o1042
30. G.R. Desiraju, T. Steiner. The Weak Hydrogen Bond in Structural Chemistry & Biology, IUCr Monograph No. 9, Oxford Press.
31. Prins L.J., Reinhoudt D.N., and Timmerman P. Angew. Chem. (Int. Ed.) 40 (2001) 2382-2426
32. Fallon III L. Acta Cryst. B29 (1973) 2549-2556
33. Voet D., and Rich A. J. Am. Chem. Soc. 91 (1969) 3069-3075
34. Portalone G., and Colapietro M. Acta Cryst. C63 (2007) o423-o425
35. Barnett S.A., Hulme A.T., and Tocher D.A. Acta Cryst. C62 (2006) o412-o415
36. Chaudhuri N.K., Montag B.J., and Heidelberger C. Cancer Res. 18 (1958) 318-328
37. Chaudhuri N.K., Mukherjee K.L., and Heidelberger C. Biochem. Pham. 1 (1959) 328-341
38. Harbers E., Chaudhuri N.K., and Heidelberger C. J. Biol. Chem. 234 (1959) 1255-1262
39. Mukherjee K.L., Bohar J., Wentland D., Ansfield F.J., and Heidelberger C. Cancer Res. 23 (1963) 49-66
40. Mukherjee K.L., and Heidelberger C. J. Biol. Chem. 235 (1960) 433-437
41. Z. Otwinowski, W. Minor, in: C.W. Carter Jr., R.M. Sweets (Eds.), Methods in Enzymol., 276: Macromolecular Crystallography, Part A, Academic Press, pp. 307-326.
42. SHELXTL: Structure Analysis Program, Version 6.10, Bruker Analytical X-ray Systems, Madison, WI, 2000.