Solution NMR conformational analysis of the potent equilibrative sensitive (ES) nucleoside transporter inhibitor, S6-(4- nitrobenzyl)mercaptopurine riboside (NBMPR)

Nucleosides and Nucleotides

Volumn 16, Issue 12, 1997, Pages 2101-2110

  Buolamwini, John K ^a   Barchi Jr , Joseph J ^b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; NUCLEOSIDE TRANSPORT INHIBITOR; S6 (4 NITROBENZYL)MERCAPTOPURINE RIBOSIDE; UNCLASSIFIED DRUG;

ARTICLE; COMPUTER PROGRAM; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; MAMMAL; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; NUCLEOSIDE TRANSPORT; SPECTROSCOPY; STRUCTURE ANALYSIS;

MAMMALIA;

EID: 0031452806     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319708002561     Document Type: Article

References (19)

1. P. G. W., Plagemann, R. M. Wohlhueter, and C. Woffendin. Nucleoside and nucleobase transport in animal cells. Biochim. Biophys. Acta 947: 405-443 (1988).
2. C. E. Cass. Nucleoside transport. In N. H. Georgopapadakou (ed.), Drug Transport in Antimicrobial and Anticancer Chemotherapy ; Marcel Dekker, New York, 1995, pp. 403-451.
3. J. K. Buolamwini. Nucleoside transport inhibitors: structure-activity relationships, and potential therapeutic applications. Curr. Med. Chem. 4: 35-66 (1997).
4. 6S, a potent inhibitor of nucleoside transport. Acta Cryst. C40: 1897-1901 (1984), and references cited therein.
5. G. D. Wu, A. S. Seriani, and R. Baker. Stereoselective deuterium exchange of methylene protons in methyl tetrafuranosides: hydroxymethyl group conformations in methyl pentafuranosides. J. Org. Chem. 48, 1750-1757 (1983).
6. C. A. G. Haasnoot, F. A. A. M. de Leeuw, H. P. M. de Leeuw, and C. Altona. The relationship between proton-proton NMR coupling constants and substituent electronegativities II. Conformational analysis of the sugar ring in nucleosides and nucleotides in solution using the generalized Karplus equation. Org. Magn. Res. 15: 43-52 (1981).
7. hh coupling constants. Program PSEUROT. J. Comp. Chem. 4: 428-437 (1983).
8. J. Van Wijk, B. H. Huckriede, J. H. Ippel, and C. Altona. Furanose sugar conformations in DNA from NMR coupling constants. Method. Enzymol. 211: 286-306 (1992).
9. L. A. Donders, F. A. A. M. de Leeuw, and C. Altona. The relationship between proton-proton NMR coupling constants and substituent electronegativities-IV. ETH set results. Magn. Res. Chem. 27: 556-563 (1989).
10. G. I. Birnbaum, and D. Shugar. Biologically active nucleosides and nucleotides: conformational features and interaction with enzymes. In S. Neidle (ed.), Nucleic Acid Structure; Part 3, VCH, New York, 1987, pp. 1-70.
11. 1H NOE difference spectroscopy: a simple graphical method based on conformationally rigid molecules. J. Org. Chem. 55: 5784-5790 (1990).
12. S. L. Moodie, and J. M. Thornton. A study into the effects of protein binding on nucleotide conformation. Nucleic Acids Res. 21, 1369-1380 (1993).
13. M. K. Gurjar, A. C. Kunwar, D. V. Reddy, A. Islam, S. V. Lalita, B. Jagannadha, and A. V. Rama-Rao. Synthesis and conformational studies on AZT and its deuterated analogues. Tetrahedron 49: 4373-4382 (1993).
14. Van Roey, P. Salerno, J. M., Chu, C. K. and Schinazi, R. F. (1989). Correlations between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus. Proc. Natl. Acad. Sci. USA 86, 3929-3933
15. S. Dijkstra, J. M. Benevides, and G. J. Thomas, Jnr. Solution conformations of nucleoside analogues exhibiting antiviral activity against human immunodeficiency virus. J. Mol. Struct. 242, 283-301 (1990).
16. E. W. Taylor, P. Van Roey, R. F. Schinazi, and C. K. Chu. A stereochemical rationale for the activity of anti-HIV nucleosides. Antiviral Chem. Chemother. 1, 163-173 (1990).
17. J. W. Quail, L. T. J. Delbaere, and A. R. P. Paterson. Structure and conformation of a tightly bound inhibitor of adenosine transport 2-amino-6-[(4-nitrobenzyl)thio]-β-D-ribofuranosylpurine. Acta Cryst. C44: 1614-1617 (1988).
18. 3OH. Nucleosides & Nucleotides 6: 877-885 (1987), and references cited therein.
19. V. N. Viswanadhan, A. K. Ghose, and J. N. Weinstein. Mapping the Binding Site of the Nucleoside Transporter Protein: A 3D-QSAR Study. Biochim. Biophys. Acta 1039: 356-366 (1990).