Alterations in purine nucleotide biosynthesis induced by 2-amino-6-chloropurine☆

Add time:09/01/2019    Source:sciencedirect.com

Exposure of sarcoma 180 ascites cells to 2-amino-6-chloropurine (6-C1G) in vivo resulted in several metabolic lesions in the pathways of purine nucleotide biosynthesis. Pronounced inhibition of the incorporation of glycine-2-14C into the guanine and adenine nucleotides of the nucleic acids, coupled with blockade of the utilization of 4-amino-5-imidazolecarboxamide-2-14C solely for the formation of guanine nucleotides, indicated the presence of a site of inhibition on the pathway of purine nucleotide formation de novo. The conversion of hypoxanthine-8-14C to nucleic acid guanine was markedly decreased by 6-CIG, whereas the utilization of this labeled precursor for the formation of nucleic acid adenine was not lowered by this agent. Under these conditions neither the incorporation of xanthine-8-14C nor of guanine-8-14C into the guanine moiety of the nucleic acids was depressed, indicating that 6-CIG or a derivative thereof inhibited the conversion of inosine 5′-phosphate to xanthosine 5′-phosphate. Blockade of this site was confirmed by the finding that 2-amino-6-chloropurine ribonucleoside 5′-phosphate inhibited the activity of inosine 5′-phosphate dehydrogenase. Molar equivalent levels of 2-amino-6-chloropurine ribonucleoside and 2-amino-6-chloropurine ribonucleoside triacetate caused a degree of inhibition of the conversion of hypoxanthine-8-14C to guanine nucleotides comparable to that produced by 6-C1G. 2-Amino-6-iodopurine ribonucleoside was at least as active an inhibitor of the formation of nucleic acid guanine as the chloro-derivatives.

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