3590-48-5Relevant articles and documents
Improved nucleic acid triggered probe activation through the use of a 5-thiomethyluracil peptide nucleic acid building block
Cai, Jianfeng,Li, Xiaoxu,Taylor, John Stephen
, p. 751 - 754 (2005)
(Chemical Equation Presented) To improve the efficiency of a nucleic acid triggered probe activation (NATPA) system a 5-thiomethyluracil peptide nucleic acid (PNA) building block has been synthesized. Attachment of imidazole and a coumarin ester to uracils at the ends of two PNAs resulted in a 550 000-fold acceleration of DNA-triggered coumarin release relative to imidazole and a 6-fold increase in kcat relative to a system which had these groups attached to the amino and carboxy ends of PNAs.
Synthesis and Spectroscopy of Phosphonate Derivatives of Uracil and Thymine. X-Ray Crystal Structure of Diethyl 6-Uracilmethylphosphonate
Ochocki, Justyn,Erxleben, Andrea,Lippert, Bernhard
, p. 1179 - 1184 (1997)
A new class of phosphonate ligands, derived from uracil and thymine was designed, prepared and characterised. Dimethyl (4, 7) and diethyl (5, 8) uracilmethylphosphonates have been prepared by the reaction of chloromethyluracil isomers 2 and 3 with trimethyl phosphite and triethyl phosphite, respectively. The corresponding free acids, 5-uracilmethylphosphonic acid 6 and 6-uracilmethylphosphonic acid 9, have also been isolated. The structure of the compounds has been assigned by nmr spectroscopy and, in the case of 8, confirmed by X-ray analysis.
C(5) modified uracil derivatives showing antiproliferative and erythroid differentiation inducing activities on human chronic myelogenous leukemia K562 cells
Brognara, Eleonora,Lampronti, Ilaria,Breveglieri, Giulia,Accetta, Alessandro,Corradini, Roberto,Manicardi, Alex,Borgatti, Monica,Canella, Alessandro,Multineddu, Chiara,Marchelli, Rosangela,Gambari, Roberto
scheme or table, p. 30 - 37 (2012/05/04)
The K562 cell line has been proposed as a useful experimental system to identify anti-tumor compounds acting by inducing terminal erythroid differentiation. K562 cells exhibit a low proportion of hemoglobin-synthesizing cells under standard cell growth conditions, but are able to undergo terminal erythroid differentiation when treated with a variety of anti-tumor compounds. In this paper we report a screening study on a set of different modified C(5) uracil derivatives for the evaluation of their antiproliferative effect in connection with erythroid differentiation pathways, and for defining a new class of drug candidates for the treatment of chronic myelogenous leukemia. Activity of the derivatives tested can be classified in two effect: an antiproliferative effect linked to a high level of erythroid differentiation activity and an antiproliferative effect without activation of gamma globin genes The highest antiproliferative effect and erythroid induction was shown by compound 9, a thymine derivative bearing a n-octyl chain on nitrogen N(1), whereas thymine did not show any effect, suggesting the importance of the linear alkyl chain in position N(1). To our knowledge this compound should be considered among the most efficient inducers of erythroid differentiation of K562 cells. This work is the starting point for the quest of more effective and specific drugs for the induction of terminal erythroid differentiation, for leading new insights in the treatment of neoplastic diseases with molecules acting by inducing differentiation rather than by simply exerting cytotoxic effects.