Sequence- and base-specific delivery of nitric oxide to cytidine and 5-methylcytidine leading to efficient deamination

Journal of the American Chemical Society

Volumn 126, Issue 29, 2004, Pages 8864-8865

  Ali, Monsur ^b   Alam, Rowshon ^b   Kawasaki, Takeshi ^a   Nakayama, Shizuka ^b   Nagatsugi, Fumi ^b   Sasaki, Shigeki ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 METHYLCYTIDINE; CYTIDINE; DNA; NITRIC OXIDE; NUCLEIC ACID BASE; OLIGODEOXYNUCLEOTIDE; TIOGUANINE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; DEAMINATION; DNA DAMAGE; ENERGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NITROSYLATION; NUCLEIC ACID SYNTHESIS; NUCLEOTIDE SEQUENCE; POINT MUTATION; POLYMERIZATION; PROTEIN STABILITY; QUANTITATIVE ANALYSIS; ROOM TEMPERATURE;

CYTIDINE; DEAMINATION; NITRIC OXIDE; NITRIC OXIDE DONORS; S-NITROSO-N-ACETYLPENICILLAMINE; SUBSTRATE SPECIFICITY; THERMODYNAMICS; THIOGUANINE;

EID: 3242771283     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0498888     Document Type: Article

References (21)

1. Moncada, S.; Palmer, R. M.; Higgs, E. A. Pharmacol. Rev. 1991, 43, 109-142.
2. Williams, D. L. H. Acc. Chem. Res. 1999, 32, 869-876.
3. Al-Sa'doni, H.; Ferro, A. Clin. Sci. 2000, 98, 507-520.
4. Lala, P. K.; Chakraborty, C. Lancet Oncol. 2001, 2, 149-156.
5. Burney, S.; Caulfield, J. L.; Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. Murat. Res. 1999, 424, 37-49.
6. Recent examples: (a) Seidman, M. M.; Glazer, P. M. J. Clin. Invest. 2003, 112,487-494.
7. (b) Zhou, Q. B.; Rokita, S. E., Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 15452-15457.
8. (c) Sasaki, S. Eur. J. Pharm. Sci. 2001, 13, 43-51 and references therein.
9. An ab initio caluculation was done at the B3LYP/6-31G* level to produce a transition state with an activation energy of 13.8 kcal/mol.
10. Kadokura, M.; Wada, T.; Seio K.; Sekine, M. J. Org. Chem. 2000, 65, 5104-5113. See also references on thionucleosides cited therein.
11. Wang, K.; Wen, Z.; Zhang, W.; Xian, M.; Cheng, J. P.; Wang, P. G. Bioorg. Med. Chem. Lett. 2001, 11, 433-436.
12. Kojima, H.; Nakatsubo, N.; Kikuchi, K.; Kawahara, S.; Kirino, Y.; Nagoshi, H.; Hirata, Y.; Nagano, T. Anal. Chem. 1998, 70, 2446-2453.
13. Nakatsubo, N.; Kojima, H.; Kikuchi, K.; Nagoshi, H.; Hirata, Y.; Maeda D.; Imai, Y.; Irimura, T.; Nagano, T. FEBS Lett. 1998, 427, 263-266.
14. Li, H.; Meininger, C. J.; Wu, G. J. Chromatogr. B 2000, 746, 199-207.
15. See Figures 7 and 9 in Supporting Information.
16. 3- found 1690.31, calcd 1689.97.
17. a values tend to produce more stable S-NO bonds: Lu, J. M.; Wittbrodt, J. M.; Wang, K.; Wen, Z.; Schlegel, H. B.; Wang, P. G.; Cheng, J. P. J. Am. Chem. Soc. 2001, 123, 2903-2904.
18. Figure 5 in Supporting Information.
19. Progress of NO transfer reaction and the detection of DAF-2 triazole are illustrated in Figures 6-9 in Supporting Information.
20. Suzuki, T.; Nakamura, T.; Yamada, M.; Ide, H.; Kanaori, K.; Tajima K.; Morii, T.; Makino, K. Biochemistry 1999, 38, 7151-7158.
21. Suzuki, T.; Yamada, M.; Nakamura, T.; Ide, H.; Kanaori, K.; Tajima, K.; Morii, T.; Makino K. Bioorg. Med. Chem. 2002, 10, 1063-1067.