56
Views
7
CrossRef citations to date
0
Altmetric
Research Article

Synthesis and in vitro evaluation of N-nicotinoylglycyl-2-(5-fluorouracil-1-yl)-d,l-glycine as a colon-specific prodrug of 5-fluorouracil

, , , , &
Pages 199-205 | Received 18 Aug 2006, Accepted 04 Jan 2007, Published online: 08 Oct 2008

References

  • Boxenbaum HG, Jodhka GS, Ferguson AC, Riegelman S, MacGregor TR. The influence of bacterial gut hydrolysis on the fate of orally administered isonicotinuric acid in man. J Pharmacokinet Biopharm 1974; 2: 211–237
  • Buur A, Bundgarrd H. Prodrugs of 5-fuorouracil. I. Hydrolysis kinetics and physicochemical properties of various N-acyl derivatives of 5-fluorouracil. Int J Pharm 1984; 21: 349–364
  • Chourasia MK, Jain SK. Pharmaceutical approaches to colon targeted drug delivery systems. J Pharm Pharm Sci 2003; 6: 33–66
  • Ho DH, Townsend L, Luna MA, Bodey GP. Distribution and inhibition of dihydrouracil dehydrogenase activities in human tissues using 5-fluorouracil as a substrate. Anticancer Res 1986; 6: 781–784
  • Jung YJ, Lee JS, Kim YM. Synthesis and in vitro/in vivo evaluation of 5-aminosalicyl-glycine as a colon-specific prodrug of 5-aminosalicylic acid. J Pharm Sci 2000; 89: 594–602
  • Jung YJ, Lee JS, Kim YM. Colon-specific prodrugs of 5-aminosalicylic acid: Synthesis and in vitro/in vivo properties of acidic amino acid derivatives of 5-aminosalicylic acid. J Pharm Sci 2001; 90: 1767–1775
  • Kingsbury WD, Boehm JC, Mehta RJ, Grappel SF, Gilvarg C. A novel peptide delivery system involving peptidase activated prodrugs as antimicrobial agents. Synthesis and biological activity of peptidyl derivatives of 5-fluorouracil. J Med Chem 1984; 27: 1447–1451
  • Lee JS, Jung YJ, Kim YM. Synthesis and evaluation of N-acyl-2-(5-fluorouracil-1-yl)-d,l-glycine as a colon-specific prodrug of 5-fluorouracil. J Pharm Sci 2001; 90: 1787–1794
  • Mukherjee KL, Heidelberger C. Studies of fluorinated pyrimidines. XV. Inhibition of the incorporation of formate-C14 into DNA thymine of Ehrlich ascites carcinoma cells by 5-fluoro-2′-deoxyuridine-5′-monophosphate and related compounds. Cancer Res 1962; 22: 815–822
  • Nakamura J, Asai K, Nishida K, Sasaki H. A novel prodrug of salicylic acid, salicylic acid–glycylglycine conjugate, utilizing the hydrolysis in rabbit intestinal microorganisms. J Pharm Pharmacol 1992; 44: 713–716
  • Nichifor M, Schacht E. Synthesis of peptide derivatives of 5-fluorouracil. Tetrahedron 1994; 50(12)3747–3760
  • Queener SF, Morris HP, Weber G. Dihydrouracil dehydrogenase activity in normal, differentiating and regnerating liver and in hepatomas. Cancer Res 1971; 31: 1004–1009
  • Ragnhammar P, Blomgren H. How to optimize the effect of 5-fluorouracil modulated therapy in advanced colorectal cancer. Med Oncol 1995; 12: 187–201
  • Rubinstein A. Microbially controlled drug delivery to the colon. Biopharm Drug Dispos 1990; 11: 465–475
  • Scheline RR. Metabolism of foreign compounds by gastrointestinal microorganisms. Pharmacol Rev 1973; 25: 451–523
  • Shareef MA, Khar RK, Ahuja A, Ahmad FJ, Raghava S. Colonic drug delivery: An updated review. AAPS PharmSci 2003; 5: E17
  • Sinha VR, Kumria R. Colonic drug delivery: Prodrug approach. Pharm Res 2001; 18: 557–564
  • Sinha VR, Kumria R. Microbially triggered drug delivery to the colon. Eur J Pharm Sci 2003; 18: 3–18
  • Suda Y, Shimidzu K, Sumi M, Oku N, Kusumoto S, Nadai T, Yamashita S. The synthesis and in vitro and in vivo stability of 5-fluorouracil prodrugs which possess serum albumin binding potency. Biol Pharm Bull 1993; 16: 876–878

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.