703-95-7 Usage
Description
5-Fluoroorotic acid (5-FOA) is a synthetic compound that has gained significant importance in molecular genetics research and as a potential antimalarial agent. It is structurally similar to orotic acid, a naturally occurring compound involved in the biosynthesis of pyrimidine nucleotides.
Used in Molecular Genetics Research:
5-Fluoroorotic acid is used as a selective agent for identifying orotidine-5'-phosphate decarboxylase mutants of Saccharomyces cerevisiae. It is employed in the selection of resistant strains that possess a mutant URA3 gene, which renders them deficient in this enzyme. This property makes 5-FOA a valuable tool for genetic studies and strain selection in yeast.
Used in Antimalarial Applications:
5-Fluoroorotic acid has demonstrated potent antimalarial activity against both chloroquine-susceptible and chloroquine-resistant clones of Plasmodium falciparum, the parasite responsible for causing malaria. Studies have shown that thymidylate synthase (TS) is the primary target of 5-FOA in malarial parasites, with its conversion to 5-fluorouridine monophosphate (5-FUMP) and subsequent toxic metabolites leading to the inhibition of DNA synthesis in the parasites.
Used in Combination Therapy for Malaria:
The combination of 5-FOA and uracil has been effective in treating mice infected with Plasmodium yoelli, a rodent malaria parasite. This suggests that 5-FOA may have potential in the treatment of human malarial infections when used in combination with other agents, offering a promising avenue for further research and development in antimalarial therapies.
Check Digit Verification of cas no
The CAS Registry Mumber 703-95-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 3 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 703-95:
(5*7)+(4*0)+(3*3)+(2*9)+(1*5)=67
67 % 10 = 7
So 703-95-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)
703-95-7Relevant articles and documents
Anticandidal activity of pyrimidine-peptide conjugates
Ti,Steinfeld,Naider,Gulumoglu,Lewis,Becker
, p. 913 - 918 (1980)
The ability of conjugates of peptides and 5-fluorocytosine or 5-fluoro-ortic acid to enter 'Candida albicans' was investigated. A number of conjugates of 5-fluoro-orotic acid and peptides were synthesized using 1-(ethoxycarbonyl)-2-ethoxy-1,2-dihydroquinoline as the coupling agent. Orotyl-L-leucyl-L-leucine, 5-fluoro-4-(N-succinamoyl-L-alanyl-L-leucine)-2(1H)-pyrimidinone [a 5-fluorocytosine derivative], and 5-fluoro-orotyl-L-leucyl-L-leucine all inhibited the uptake of trimethionine into 'C. albicans' WD 18-4. Inhibition by 5-fluoro-orotyl-L-leucine was competitive, as judged using double-reciprocal plots. Evaluation of minimum inhibitory concentrations of peptide - 5 - fluorocytosine conjugates suggest that these conjugates enter 'C. albicans' in the intact form. These results provide the first experimental evidence that peptides can carry pyrimidines into a eukaryote.
An improved synthesis and mass fragmentometry of 5 fluoroorotic acid
Alam,Shires,Aboul Enein
, p. 375 - 378 (2007/10/06)
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