Bis(carbamoyloxymethyl) esters of 2′,3′-dideoxyuridine 5′-monophosphate (ddUMP) as potential ddUMP prodrugs

Pharmaceutical Research

Volumn 22, Issue 3, 2005, Pages 390-396

  Khan, Saeed R ^a   Kumar, Srinivas K ^a   Farquhar, David ^b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

2 ,3 dideoxyuridine 5 monophosphate; Membrane permeable prodrugs; Nanticancer

Indexed keywords

(N PIPERIDINOCARBAMOYLOXYMETHYL) 2',3' DIDEOXYURIDINE 5' PHOSPHATE; (N,N' DIMETHYLCARBAMOYLOXYMETHYL) 2',3' DIDEOXYURIDINE 5' PHOSPHATE; BATROXOBIN; BIS(N PIPERIDINOCARBAMOYLOXYMETHYL) 2',3' DIDEOXYURIDINE 5' PHOSPHATE; BIS(N,N' DIMETHYLCARBAMOYLOXYMETHYL) 2',3' DIDEOXYURIDINE 5' PHOSPHATE; CARBOXYLIC ACID DERIVATIVE; DEOXYURIDINE DERIVATIVE; PHOSPHODIESTERASE I; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIFFUSION; DRUG DEGRADATION; DRUG DESIGN; DRUG STABILITY; DRUG SYNTHESIS; ENZYME DEGRADATION; HUMAN; INCUBATION TIME; MITSUNOBU REACTION; PH MEASUREMENT; PLASMA HALF LIFE; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN HYDROLYSIS;

ANIMALS; CROTALID VENOMS; DIDEOXYNUCLEOSIDES; ESTERS; HUMANS; PRODRUGS;

EID: 17644377247     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11095-005-1876-4     Document Type: Article

References (21)

1. J. Beres, W. G. Bentrude, G. Kruppa, P. A. McKernan, and R. K. Robins. Synthesis and antitumor and antiviral activities of a series of 1-beta-D-ribofuranosyl-5-halocytosine (5-halocytidine) cyclic 3′,5′-monophosphates. J. Med. Chem. 28:418-422 (1985).
2. N. W. Bischofberger, R. J. Jones, M. N. Arimilli, K. Y. Lin, M. S. Louie, L. R. McGee, E. J. Prisbe, W. A. Lee, and K. C. Cundy. Preparation of viricidal nucleotide analogs. PCT Int. Appl. 154 pp. (1995).
3. P. D. Cook, G. Wang, T. W. Bruice, V. Rajappan, K. Sakthivel, K. D. Tucker, J. L. Brooks, J. M. Leeds, M. E. Ariza, and P. C. Fagan. Preparation of nucleotide 5′-monophosphate mimics and their prodrugs useful as antiviral, antibacterial, anticancer, and immunomodulatory agents. PCT Int. Appl. 75 pp. (2003).
4. S. Warren. Targetable nucleotide-based prodrugs with cleavable ester linkages. PCT Int. Appl. 137 pp. (1999).
5. 32P-labeled ribonucleotides in tissue slices and cell suspensions. J. Biol. Chem. 316:823-830 (1955).
6. P. M. Roll, H. Weinfeld, E. Carroll, and G. B. Brown. The utilization of nucleotides by the mammal. IV. Triply labeled purine nucleotides. J. Biol. Chem. 220:439-454 (1956).
7. D. Farquhar, D. N. Srivastava, N. J. Kuttesch, and P. P. Saunders, Biological reversible phosphate protective groups. J. Pharm. Sci. 72:324-325 (1983).
8. S. Khan, B. Nowak, W. Plunkett, and D. Farquhar. Nucleotide bis(pivaloyloxy methyl)esters bypass nucleoside kinase deficiency. Proc. Am. Assoc. Cancer Res. 31:425-426 (1990).
9. K. J. Sastry, P. N. Nehete, S. Khan, W. Plunkett, R. B. Arlinhaus, and D. Farquhar. A newstrategy for the chemotherapy of acquired immune immunodeficiency syndrome: membrane permeable dideoxyuridine monophosphate analogs as a potent inhibitors of human immunodeficiency virus infection. Mol. Pharmacol. 41:441-445 (1992).
10. D. Farquhar, S. Khan, D. N. Srivastva, and P. P. Saunders. Synthesis and antitumor evaluation of Bis[(pivaloyloxy)methyl] 2′-Deoxy-5-fluorouridine 5′-Monophosphate (FdUMP): A strategy to introduce nucleotides into cells. J. Med. Chem. 37:3902-3909 (1994).
11. D. N. Srivastva and D. Farquhar. Bioreversible phosphate protective groups: synthesis and stability of model acyloxymethyl phosphates. Bioorg. Chem. 12:118-129 (1984).
12. O. Mitsunobo. The use of diethyl azadicarboxylate and triphenylphosphine in the synthesis and transformation of natural products. Synthesis (Mass.) 1:1-28 (1981).
13. A. J. Kirby. New synthesis of monoalkyl phosphates. Chem. Ind. (London) 47:1877-1878 (1963).
14. S. Khan. Design, synthesis and biological evaluation of 5′-mononucleotide prodrugs: Strategies to introduce nucleotides into cells. Ph.D. Dissertation UT M.D. Anderson Cancer Center, Houston, TX (1997).
15. S. R. Khan and D. Farquhar. Bis(N,N-dimethylcarbamoyloxymethyl) 2′,3′-dideoxyuridine 5′-monophosphate (DM2-ddUMP): a potential ddUMP prodrug. Tetrahedron Lett. 40:607-610 (1999).
16. H. F. Haugen and S. Skrede. Nucleotide pyrophosphate and phosphodiesterase I. Organ distribution and activities in body fluids. Clin. Chem. 23:1531-1537 (1977).
17. M. Land, R. A. Everard, and L. G. Butler. 5′-Nucleotide phosphodiesterase: features of substrate binding site as deduced from specificity and kinetics of some novel substrates. Biochemistry 19:138-143 (1980).
18. H. G. Khorana and W. E. Razell. Studies on polynucleotides. III. Enzymic degradation: substrate specificity and properties of snake venom phosphodiesterase. J. Bio. Chem. 234:2105-2113 (1959).
19. H. Fukazawa, T. Nishimura, N. Tanaka, and H. Suzuki. 5′-Nucleotide phosphodiesterase and alkaline phospatase in tumor cells: evidence for existence of novel species in the cytosol. Biochim. Biophys. Acta 966:99-106 (1988).
20. H. G. Boman. Snake venom phosphodiesteras exonuclease action. Nature 180:1181-1184 (1957).
21. M. Yoshikawa, T. Kato, and T. Takenishi. A novel method for phosphorylation of nucleosides to 5′-nucleotides. Tetrahedron Lett. 8:5065-5068 (1967).