Abstract
It was recognized about two decades ago that analogs of nucleic acid bases could be utilized as substrates for incorporation into polynucleotides, resulting in the formation of “fraudulent” nucleic acids containing an aberrant base. Among the compounds most extensively studied which are able to replace a base in nucleic acids are 8-azaguanine, 2-thiouracil, 5-bromouracil, 5-fluorouracil, 6-azathymine and 6-thioguanine. The total number of analogs which are incorporated into polynucleotides is quite limited. A general review on metabolite analog incorporation appeared in 1958 (Matthews, 1958) which described the functions associated with the presence of such an abnormal base in nucleic acids. Because most of the analogs had carcinostatic activity, the anabolism and catabolism of such compounds in relation to their biochemical and chemotherapeutic actions was the subject of another review (Mandel, 1959).
This review was supported in part by USPHS Grant CA 02978 from the National Cancer Institute, N.I.H., Bethesda, Maryland.
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References
Andon, T., and E. Chargaff: Formation and fate of abnormal ribosomes of E. coli cells treated with 5-fluorouracil. Proc. nat. Acad. Sci. (Wash.) 54, 1181–1189 (1965).
Aposhian, H. V., and A. Kornberg: Enzymatic synthesis of deoxyribonucleic acid. IX. The polymerase formed after T2 bacteriophage infection of Escherichia coli: A new enzyme. J. biol. Chem. 237, 519–525 (1962).
Aronson, A. I.: The inhibition of bacteriophage protein synthesis by 5-fluorouracil. Biochim. biophys. Acta (Amst.) 49, 89–97 (1961).
Aronson, A. I.: The effect of 5-fluorouracil on bacterial protein and ribonucleic acid synthesis. Biochim. biophys. Acta (Amst.) 49, 98–107 (1961).
Aronson, A. I., and M. R. Del Valle: Rna and protein synthesis required for bacterial spore formation. Biochim. biophys. Acta (Amst.) 87, 267–276 (1964).
Barnett, W. E., and H. E. Brockman: Induced phenotypic reversion by 8-azaguanine and 5-fluorouracil. Biochem. biophys. Res. Commun. 7, 199–203 (1962).
Beéarevié, A., B. Djordjevie, and D. Surfé: Effect of ultra-violet light on tobacco mosaic virus containing 5-fluorouracil. Nature (Lond.) 198, 612–613 (1963).
Ben-Hamida, F., and D. Schlessinger: Stability of ß-galactosidase messenger ribonucleic acid in Escherichia coli. J. Bact. 90, 1611–1616 (1965).
Ben-Ishai, R., B. Z. Cavari, H. Goldin, and S. Kerpel: On the mechanism of 5-fluoro-uracil-induced resistance to ultraviolet irradiation in Escherichia coli. Biochim. biophys. Acta (Amst.) 95, 291–301 (1965).
Bodmer, W. F., and S. Grether: Uptake and incorporation of thymine, thymidine, uracil, uridine, and 5-fluorouracil into the nucleic acids of Bacillus subtilis. J. Bact. 89, 1011–1014 (1965).
Bonner, J., and J. A. D. Zeevaart: Ribonucleic acid synthesis in the bud, an essential component of floral induction in Xanthium. Plant Physiol. 37, 43–49 (1962).
BoscH, L., E. Harmers, and C. Heidelberger: Studies on fluorinated pyrimidines. V. Effects on nucleic acid metabolism in vitro. Cancer Res. 18, 335–343 (1958).
Brockman, R. W., and E. P. Anderson: Pyrimidine analogues. In: Metabolic inhibitors, I. pp. 239–285.
Hochsrer, R. M., and J. H. Quastel, Eds. New York: Academic Press 1963.
Hochsrer, R. M., J. M. Davis, and P. Srurrs: Metabolism of uracil and 5-fluorouracil by drug-sensitive and by drug-resistant bacteria. Biochim. biophys. Acta (Amst.) 40, 22–32 (1960).
Bujard, H., and C. Heidelberger: Fluorinated pyrimidines. XXVII. Attempts to determine transcription errors during the formation of fluorouracil-containing messenger ribonucleic acid. Biochemistry 5, 3339–3345 (1966).
Bull, M. J., and J. Lascelles: The association of protein synthesis with the formation of pigments in some photosynthetic bacteria. Biochem. J. 87, 15–28 (1963).
Bussard, A., S. Naono, F. Groset J. Monod: Effets d’un analogue de l’uracile sur les propriétés d’une protéine enzymatique synthétisée en sa présence. C. R. Acad. Sci. (Paris) 250, 4049–4051 (1960).
Erna, J., J. Rychl1k, D. Grünberger, and F. Dorm: The effect of 5-fluorouracil-containing ribonucleic acid on protein synthesis by Escherichia coli in vivo. Coll. Czech. Chem. Commun. 28, 1215–1223 (1963).
Champs, S. P. and S. Benzer: Reversal of mutant phenotypes by 5-fluorouracil: An approach to nucleotide sequences in messenger-RNA. Proc. nat. Acad. Sci. (Wash.) 48, 532–546 (1962).
Chaudhuri, N. K., B. J. Montag, and C. Heidelberger: Studies On fluorinated pyrimidines. III. The metabolism of 5-fluorouracil-2-C14 and 5-fluoroorotic-2-C14 acid in vivo. Cancer Res. 18, 318–328 (1958).
Cherry, J. H., and R. Van Huystee: Effects of 5-fluorouracil on photoperiodic induction and nucleic acid metabolism of Xanthium. Plant Physiol. 40, 987–993 (1965).
Cohen, S. S., J. G. Flaks, H. D. Barner, M. R Loeb, and J. Lichtenstein: The mode of action of 5-fluorouracil and its derivatives. Proc. nat. Acad. Sci. (Wash.) 44, 1004–1012 (1958).
Cooper, P. D.: The mutation of poliovirus by 5-fluorouracil. Virology 22, 186–192 (1964).
Cooper, S., and N. D. Zinder: The growth of an RNA bacteriophage: The role of DNA synthesis. Virology 18, 405–411 (1962).
Dagg, C. P., A. Doerr, and C. Offurr: Incorporation of 5-fluorouracil-2-C14 by mouse embryos. Biol. Neonat. (Basel) 10, 32–46 (1966).
Davern, C. I.: The inhibition and mutagenesis of an RNA bacteriophage by 5-fluorouracil. Austral. J. biol. Sci 17, 726–737 (1964)
Davern, C. I., and J. Bonner: The influence of 5-fluorouracil on tobacco-mosaic virus production in tobacco-leaf discs. Biochim. biophys. Acta (Amst.) 29, 205–206 (1958).
De Kloft, S. R.: Effects of 5-fluorouracil and 6-azauracil on the synthesis of ribonucleic acid and protein in Saccharomyces carlsbergensis. Biochem. J. 106, 167–178 (1968).
De Kloft, S. R., and P. J. Strijkert: Selective inhibition of ribosomal RNA synthesis in Saccharomyces carlsbergensis by 5-fluorouracil. Biochem. biophys. Res. Commun. 23, 49–55 (1966).
Del Valle, M. R., and A. I. Aronson: Evidence for the synthesis of stable informational RNA required for bacterial spore formation. Biochem. biophys. Res. Commun. 9, 421–425 (1962).
Duschinsky, R., E. Pleven, and C. Heidelberger: The synthesis of 5-fluoropyrimidines. J. Amer. chem. Soc. 79, 4559–4560 (1957).
Ebel, J. P., J. H. Weil, B. Retheret J. Heinrich: Nature des sites responsables de l’acti-vité acceptrice du s-RNA. Bull. Soc. Chim. biol. (Paris) 47, 1599–1608 (1965).
Elion, G. B., and G. H. Hitchings: Metabolic basis for the actions of analogs of purines and pyrimidines. In: Advanc. Chemotherapy 2, 91–177 (1965).
Fikus, M., K. L. Wierzchowski, and D. Shugar: Reversible photochemical transformation of 5-fluorouracil analogues and poly-5-fluorouridylic acid. Biochem. biophys. Res. Commun. 16, 478–483 (1964).
Gaetani, S., and M. A. Spadoni: Effect of 5-fluorouracil on hepatic induced increase of tryptophan-pyrrolase. Nature (Lond.) 191, 1296–1297 (1961).
Galun, E., and J. Gressel: Morphogenesis in trichoderma: Suppression of photoinduction by 5-fluorouracil. Science 151, 696–698 (1966).
Garen, A., and O. Stnniqi: Suppression of mutations in the alkaline phosphatase structural cistron of E. coli. Proc. nat. Acad. Sci. (Wash.) 48, 1121–1127 (1962).
Garren, L. D., R. R. Howell, G. M. Tomkins, and R. M. Crocco: A paradoxical effect of actinomycin D: The mechanism of regulation of enzyme synthesis by hydrocortisone. Proc. nat. Acad. Sci. (Wash.) 52, 1121–1129 (1964).
Goldberg, A. R., J. H. Machledt, JR., and A. B. Pardee: On the action of fluorouracil on leukemia cells. Cancer Res. 26, 1611–1615 (1966).
Goodman, F.: Nucleic acid metabolism and bacteriophage multiplication: Effects of 5-fluorouracil on coliphage synthesis. Virology 21, 249–257 (1963).
Goodman, F.: Partial satisfaction of a uracil requirement by 5-fluorouracil. J. Bact. 89, 1156–1157 (1965).
Gordon, M. P., and M. Staehelin: The incorporation of 5-fluorouracil into the nucleic acid of tobacco mosaic virus. J.A mer. chem. Soc. 80, 2340–2341 (1958).
Gordon, M. P., and M. Staehelin: Studies on the incorporation of 5-fluorouracil into a virus nucleic acid. Biochim. biophys. Acta (Amst.) 36, 351–361 (1959).
Graham, A. F., and C. Kirk: Effect of 5-fluorouracil on the growth of bacteriophage R17. J. Bact. 90, 928–935 (1965).
Gray, P. N., and M. Rachmeler: The effects of 5-fluorouracil and 6-thioguanine incorporation on the amino acid acceptor activity of Escherichia coli tRNA. Biochim. biophys. Acta (Amst.) 138, 432–435 (1967).
Gressel, J., and E. Galun: Effect of 5-fluorouracil on the soluble RNA of Trichoderma. Biochem. biophys. Res. Commun. 24, 162–168 (1966).
Gros, F., W. Gilbert, H. H. Hiatt, G. Attardi, P. F. Spahr, and J. D. Watson: Mole-cular and biological characterization of messenger RNA. Cold Spr. Harb. Symp. quant. Biol. 26, 111–126 (1961).
Gros, F., W. Gilbert, H. H. Hiatt, G. Attardi, P. F. Spahr, and S. Naono: Bacteria] synthesis of “modified” enzymes in the presence of a pyrimidine analogue. In: Protein biosynthesis, pp. 195–205. Harris, R. J. C., Ed. London: Academic Press 1961.
Gros, F., W. Gilbert, H. H. Hiatt, G. Attardi, P. F. Spahr, D. Hayes, F. Hayeset J. D. Watson: Etude du role de l’ARN dans le transfert de l’information génétique. Colloq. Intern. Centre Nat. Rech. Sci (Paris) 106, 437–459 (1962).
Grunberg-Manago, M., and A. M. Michelson: Polynucleotide analogues IV. Polyfluorouridylic acid and copolymers containing fluorouridylic acid. Biochim. biophys. Acta (Amst.) 87, 593–600 (1964).
Grünberger, D., and H. G. Mandel: Enhanced messenger activity of RNA from 8-azaguanine-treated Bacillus cereus. Molec. Pharmacol. 1, 157–162 (1965).
Grünberger, D., and H. G. Mandel: Effect of 5-fluorouraci] on ribosomal synthesis in Bacillus cereus. Fed. Proc. 26, 729 (1967).
Barbers, E., N. K. Chaudhuri, and C. Heidelberger: Studies on fluorinated pyrimidines. VIII. Further biochemical and metabolic investigations. J. biol. Chem. 234, 1255–1262 (1959).
Heidelberger, C.: Fluorinated pyrimidines. In: Progr. Nucl. Acid Res. and Molec. Biol. 4, 1–50 (1965).
Heidelberger, C., N. K. Chaudhuri, P. Danneberg, D. Mooren, L. Griesbach, R. Duschinsky, R. J. Schnitzer, E. Pleven, and J. Scheiner: Fluorinated pyrimidines, a new class of tumor-inhibitory compounds. Nature (Lond.) 179, 663–666 (1957).
Heidelberger, C., A. Giiobar, R. K. Baker, and K. L. Mukherjee: (1) Studies on fluorinated pyrimidines. X. In vivo studies on tumor resistance. Cancer Res. 20, 897–902 (1960).
Heidelberger, C., G. Kaldor, K. L. Mukherjee, and P. B. Danneberg: Studies on fluorinated pyrimidines. XI. In vitro studies on tumor resistance. Cancer Res. 20, 903–909 (1960).
Hignett, R. C.: The incorporation of 5-fluorouracil by Staphylococcus aureus (strain Duncan). II. Biochim. biophys. Acta (Amst.) 91, 584–591 (1964).
Hignett, R. C.: The incorporation of 5-fluorouracil by Staphylococcus aurea: (strain Duncan). III. Biochim. biophys. Acta (Amst.) 95, 538–543 (1965).
Hignett, R. C.: Interference of 5-fluorouracil in the biosynthesis of ribosomes in Staphylococcus aureus (strain Duncan). Biochim. biophys. Acta (Amst.) 114, 559–564 (1966).
Hills, D. C., and J. Horowitz: Ribosome synthesis in Escherichia coli treated with 5-fluorouracil. Biochemistry 5, 1625–1632 (1966).
Holoubek, V.: The composition of tobacco mosaic virus protein after the incorporation of 5-fluorouracil into the virus. J. molec. Biol. 6, 164–166 (1963).
Horowitz, J., and E. Chargaff: Massive incorporation of 5-fluorouracil into a bacterial ribonucleic acid. Nature (Lond.) 184, 1213–1215 (1959).
Horowitz, J., and E. Chargaff, and V. Kohlmeier: Formation of active ß-galactosidase by Escherichia coli treated with 5-fluorouracil. Biochim. biophys. Acta (Amst.) 142, 208–218 (1967).
Horowitz, J., J. J. Saukkonen, and E. Chargaff: Effect of 5-fluorouracil on a uracil-requiring mutant of Escherichia coli. Biochim. biophys. Acta (Amst.) 29, 222–223 (1958).
Horowitz, J.: Effects of fluoropyrimidines on the synthesis of bacterial proteins and nucleic acids. J. biol. Chem. 235, 3266–3272 (1960).
Iwabuchi, M., E. Otaka, M. Kono, and S. Osawa: The effect of 5-fluorouracil on the ribosome formation in Escherichia coli. Biochim. biophys. Acta (Amst.) 114, 83–94 (1966).
Jacob, F., and J. Monod: Genetic regulatory mechanism in the synthesis of proteins. J. molec. Biol. 3, 318–356 (1961).
Kadowaki, K., J. Hosoda, and B. Maruo: Effects of actinomycin D and 5-fluorouracil on the formation of enzymes in Bacillus subtilis. Biochim. biophys. Acta (Amst.) 103, 311 —318 (1965).
Kahan, F. M., and J. Huawltz: The role of deoxyribonucleic acid in ribonucleic acid synthesis. IV. The incorporation of pyrimidine and purine analogues into ribonucleic acid. J. biol. Chem. 237, 3778–3785 (1962).
Kaplan, H. S., K. C. Smith, and P. A. Tomlin: Effect of halogenated pyrimidines on radio-sensitivity of E. coli. Radiat. Res. 16, 98–113 (1962).
Kempner, E. S.: The selection and utilization of metabolic analogs for nucleic acid synthesis. Biochim. biophys. Acta (Amst.) 53, 111–122 (1961).
Kempner, E. S., and J. H. Miller: Alteration of carbon metabolism by a base analog. Biophys. J. 2, 327–337 (1962).
Kempner, E. S.: The mechanism of action of purine and pyrimidine analogs in microorganisms. Biochim. biophys. Acta (Amst.) 76, 341–346 (1963).
Kessel, D., T. C. Hall, and I. Wodinsky: Nucleotide formation as a determinant of 5-fluorouracil response in mouse leukemias. Science 154, 911–913 (1966).
Key, J. L.: Effect of purine and pyridimine analogues on growth and RNA metabolism in the soybean hypocotyl: The selective action of 5-fluorouracil. Plant Physiol. 41, 12571264 (1966).
Key, J. L., and J. Ingle: Requirement for the synthesis of DNA-like RNA for growth of excised plant tissue. Proc. nat. Acad. Sci. (Wash.) 52 1382 —1388(1964).
Kilgore, W. W., and R. R. Painter: The effect of 5-fluorouracil on the viability of house fly eggs. J. Econ. Entomology 55, 710–712 (1962).
Kilgore, W. W., and R. R. Painter,: nsect chemosterilants: Incorporation of 5-fluorouracil into house fly eggs. J. Econ. Entomology 59, 746–747 (1966).
Klubes, P., and K. L. Hartmann: The differential effects of 8-azaguanine, 5-fluorouracil, 6-mercaptopurine, and 6-thioguanine on the activities of some Krebs cycle enzymes in cell-free extracts from Bacillus cereus. Biochem. Pharmacol., in press (1969).
Koechlin, B. A., F. Rubio, S. Palmer, T. Gabriel, and R. Duschinsky: The metabolism of 5-fluorocytosine-2–14C and of cytosine-14C in the rat and the disposition of 5-fluorocytosine-2–14C in man. Biochem. Pharmacol. 15, 435–446 (1966).
Kono, M., and S. Osawa: Intermediary steps of ribosome formation in Escherichia coli. Biochim. biophys. Acta (Amst.) 87, 326–334 (1964).
Kono, M., E. Otaka, and S. Osawa: Changes in sedimentation properties of ribosomal ribonucleic acids during the course of ribosome formation in Escherichia coli. Biochim. biophys. Acta (Amst.) 91, 612–618 (1964).
Kramer, G., H. G. Wirrmann und H. Schuster: Die Erzeugung von Mutanten des Tabakmosaikvirus durch den Einbau von Fluoruracil in die Virusnucleinsäure. Z. Naturforsch. 19b, 46–51 (1964).
Kröger, H., und B. Greuer• Einfluß von Antagonisten des Nucleinsäurestoffwechsels und von Röntgenstrahlen auf die Induktion von Enzymen. Biochem. Z. 341, 190–198 (1965).
Lampkin-Hibbard, J. M., K. L. Mukherjee, and C. Heidelberger: Effects of steroids and fluoropyrimidines on lymphomas. II. In vivo studies on tumor resistance and collateral sensitivity. Cancer Res. 23, 468–476 (1963).
Lengyel, P., J. F. Speyer, and S. Ochoa: Synthetic polynucleotides and the amino acid code. Proc. nat Acad. Sci. (Wash.) 47, 1936–1942 (1961).
Lodish, H. F., S. Cooper, and N. D. Zinder: Host-dependent mutants of the bacteriophage f2. IV. On the biosynthesis of a viral RNA polymerase. Virology 24, 60–70 (1964).
Lodish, H. F., K. Horiuchi, and N. D. Zinder: Mutants of the bacteriophage f2 V. On the production of noninfectious phage particles. Virology 27, 139–155 (1965).
Lowrie, R. J., and P. L. Bergquist: Transfer ribonucleic acids from Escherichia coli treated with 5-fluorouracil. Biochemistry 7, 1761–1770 (1968).
Lozeron, H. A., and M. P. Gordon: Ultraviolet sensitization and photoreactivation of tobacco mosaic virus ribonucleic acid containing 5-fluorouraci1. Biochemistry 3, 507–510 (1964).
Lozeron, H. A., and M. P. Gordon, T. Gabriel, W. Tutz, and R. Duschinsky: The photochemistry of 5-fluorouracil. Biochemistry 3, 1844–1850 (1964).
Madison, J. T., G. A. Evererr, and H. Kung: Nucleotide sequence of a yeast tyrosine transfer RNA. Science 153 531–534 (1966).
Mandel, H. G.: The physiological disposition of some anticancer agents. Pharmacol. Rev. 11, 743–838 (1959).
Mandel, H. G., R. Markham, and R. E. F. Marchews: The distribution of thiouiacil in nucleic acid of tobacco mosaic virus. Biochim. biophys. Acta (Amst.) 24, 205–206 (1957).
Marver, H. S., A. Collins, D. P. Tschudy, and M. Reghcigl, JR.: 6-Am1n0le VU11II1C acid synthetase. II. Induction in rat liver. J. biol. Chem. 241, 4323–4329 (1966).
Massoulié, J., A. M. Michelson, and F. Pochon: Polynucleotide analogues VI. Physical studies on 5-substituted pyrimidine polynucleotides. Biochim. biophys. Acta (Amst.) 114, 16–26 (1966).
Marrxews, R. E. F.: Biosynthetic incorporation of metabolic analogues. Pharmacol. Rev. 10, 359–406 (1958).
Mukherjee, K. L., A. R. Curaeri, M. Javid, and C. Heidelberger: Studies on fluorinated pyrimidines. XVII. Tissue distribution of 5-fluorouracil-2-C14 and 5-fluoro-2’-deoxyuridine in cancer patients. Cancer Res. 23, 67–77 (1963).
Munyon, W., and N. P. Salzman: The incorporation of 5-fluorouracil into poliovirus. Virology 18, 95–101 (1962).
Nakada, D.: Formation of ribosomes by a “relaxed” mutant of Escherichia coli. J. molec. Biol. 12, 695–725 (1965).
Nakada, D., and B. Magasanik: The roles of inducer and catabolite repressor in the synthesis of ß-galactosidase by Escherichia coli. J. molec. Biol. 8, 105–127 (1964).
Naono, S., et F. Gros: Effets d’un analogue de base nucléique sur la biosynthèse de protéines bactériennes. C.angements de la composition globale des protéines. C. R. Acad. Sci. (Paris) 250, 3527–3529 (1960).
Naono, S., et F. Gros,: Synthèse par E. coli d’une phosphatase modifiée en présence d’un analogue pyrimidique. C. R. Acad. Sci. (Paris) 250, 3889–3891 (1960).
Nemeth, A. M.: The effect of 5-fluorouracil on the developmental and adaptive formation of tryptophan pyrrolase. J. biol. Chem. 237, 3703–3706 (1962).
Otaka, E., S. Osawa, and A. Sibatani: Stimulation of 14C-leucine incorporation into protein in vitro by ribosomal RNA of Escherichia coli. Biochem. biophys. Res. Commun. 15, 568–574 (1964).
Pardee, A. B., and L. S. Prestidge: The initial kinetics of enzyme induction. Biochim biophys. Acta (Amst.) 49, 77–78 (1961).
Pitot, H. C., and C. Peraino: Studies on the induction and repression of enzymes in rat liver. I. Induction of threonine dehydrase and ornithine-S-transaminase by oral intubation of casein hydrolysate. J. biol. Chem. 239, 1783–1788 (1964).
Reich, M., and H. G. Mandel: Uracil: Failure to restore DNA synthesis while relieving 5-fluorouracil-induced inhibition. Science 145, 276–277 (1964).
Reich, M., and H. G. Mandel: Dissociation of cellular functions in Bacillus cereus by 5-fluorouracil. J. Bact. 91, 517–523 (1966).
Rich, M. A., J. L. Bolaffi, J. E. Knoll, L. Cheong, and M. L. Eidinoff: Growth inhibition of a human tumor cell strain by 5-fluorouracil, 5-fluorouridine, and 5-fluoro-2’deoxyuridine — Reversal studies. Cancer Res. 18, 730–735 (1958).
Rogers, H. J., and H. R. Perkins: 5-Fluorouracil and mucopeptide biosynthesis by Staphylococcus aureus. Biochem. J. 77, 448–459 (1960).
Rosen, B.: Characteristics of 5-fluorouracil-induced synthesis of alkaline phosphatase. J. molec. Biol. 11, 845–850 (1965).
Rutman, R. J., A. Cantarow, and K. E. Paschkis: Studies in 2-acetylaminofluorene carcinogenesis. III. The utilization of uracil-2-C14 by preneoplastic rat liver and rat hepatoma. Cancer Res. 14, 119–123 (1954).
Saunders, P. P., G. A. Schultz, R. E. Bass, and G. F. Saunders: Effects of 5-fluorouracil on a uracil and thymine requiring strain of Bacillus subtilis. Bact. Proc. 1968, 131.
Sells, B. H., and K. Crudup: Ribosome production during recovery from puromycin treatment: Influence of 5-fluorouracil. Biochim. biophys. Acta (Amst.) 123, 253–264 (1966).
Shimura, Y., and D. Nathans: The preparation of coliphage MS2 containing 5-fluorouracil. Biochem. biophys. Res. Commun. 16, 116–120 (1964).
Shimura, Y., R. E. Moses, and D. Nathans: Coliphage MS2 containing 5-fluorouracil. I. Preparation and physical properties. J. molec. Biol. 12, 266–279 (1965).
Shimura, Y., R. E. Moses, and D. Nathans: Coliphage MS2 containing 5-fluorouracil. II. RNA-deficient particles formed in the presence of 5-fluorouracil. J. molec. Biol. 28, 95–102 (1967).
Singer, M. F., and P. Leder: Messenger RNA: An evaluation. Ann. Rev. Biochem. 35, 195–230 (1966).
Skoda, J., and R. E. Handschumacher: The influence of certain antimetabolites on the incorporation of orotic acid into pseudouridine in animals. Biochim. biophys. Acta (Amst.) 68, 481–483 (1963).
Slapikoff, S., and P. Berg: Mechanism of ribonucleic acid polymerase action. Effect of nearest neighbors on competition between uridine triphosphate and uridine triphosphate analogs for incorporation into ribonucleic acid. Biochemistry 6, 3654–3658 (1967).
Soffer, R. L.: Studies on the biological activity of ribonucleic acid isolated from Escherichia coli after exposure to 5-fluorouracil. Biochim. biophys. Acta (Amst.) 87, 416–422 (1964).
Staehelin, M.: Chemical modifications of virus infectivity: Reactions of tobacco mosaic virus and its nucleic acid. Experientia (Basel) 16, 473–483 (1960).
Staehelin, M., and M. P. Gordon: Effects of halogenated pyrimidines on the growth of tobacco mosaic virus. Biochim. biophys. Acta (Amst.) 38, 307–315 (1960).
Sueoka, N., and T. Yamane: Fractionation of aminoacyl-acceptor RNA and the coding problem. In: Informational Macromolecules, pp. 205–227.
Vogel, H. J., V. Bryson, and J. O. Lampen, Eds. New York: Academic Press 1963.
Sundaram, T. K.: Phenotypic reversal by 5-fluorouracil of the auxotrophy of am mutants of Stine, crassa. Biochim. biophys. Acta (Amst.) 138, 611–613 (1967).
Jutic, D., and B. Djordjevre: Effect of 5-fluorouracil on antigenic properties of tobacco mosaic virus. Nature (Lond.) 203, 434–435 (1964).
Seer, W., and D. Shugar: Preparation of poly-5-fluorouridylic acid and the properties of halogenated poly-uridylic acids and their complexes with poly-adenylic acid. Acta biochim pol. 10, 219–231 (1963).
Tershak, D. R.: Effect of 5-fluorouracil on poliovirus growth. Virology 24, 262–269 (1964).
Tershak, D. R.: Effect of 5-fluorouracil on poliovirus-induced RNA polymerase. J. molec. Biol. 21, 43–50 (1966).
Tomasz, A., and E. Borek: The mechanism of an osmotic instability induced in E. coli K-12 by 5-fluorouracil. Biochemistry 1, 543–552 (1962).
Tooze, J., and K. Weber: Isolation and characterization of amber mutants of bacteriophage R17. J. molec. Biol. 28, 311–330 (1967).
Wachsman, J. T., S. Kemp, and L. Hogg: Comparative effects of 5-fluorouracil on strains of Bacillus megaterium. J. Bact. 87, 1011–1018 (1964).
Wagner, N. J., and C. Heidelberger: Some effects of 5-fluoroorotic acid and 5-fluorouracil on the soluble ribonucleic acid of rat liver. Biochim. biophys. Acta (Amst.) 61, 373–379 (1962).
Wahba, A. J., R. S. Gardner, C. Basilio, R. S. Miller, J. F. Speyer, and P. Lengyel: Synthetic polynucleotides and the amino acid code. VIII. Proc. nat. Acad. Sci. (Wash.) 49, 116–122 (1963).
White, P. J., and C. A. Nichol: Effects of uracil and thymidine on the development of resistance to 5-fluorouracil in Pediococcus cerevisiae. J. Bact. 85, 97–105 (1963).
Willén R., and U. Stenram: RNA synthesis in the liver of rats treated with 5-fluorouracil. Arch. Biochem. Biophys. 119, 501–503 (1967).
Wittmann, H. G.: Proteinanalysen von chemisch induzierten Mutanten des Tabakmosaik-virus. Z. Vererbungsl. 95, 333–344 (1964).
Wittmann-Liebold, B., and H. G. Wirrmann: Lokalisierung von Aminosäureaustauschen bei Spontanmutanten and nach Fluoruracileinbau isolierten Mutanten des Tabakmosaikvirus. Z. Vererbungsl. 97, 218–225 (1965).
Wittmann-Liebold, B., and H. G. Wirrmann: Lokalisierung von Aminosäureaustauschen bei Nitritmutanten des Tabakmosaik-virus. Z. Vererbungsl. 97, 305–326 (1965).
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Mandel, H.G. (1969). The Incorporation of 5-Fluorouracil Into RNA and its Molecular Consequences. In: Hahn, F.E. (eds) Progress in Molecular and Subcellular Biology. Progress in Molecular and Subcellular Biology, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46200-9_4
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