Studies in Chemotherapy. VIII. Methionine and Purine Antagonists and their Relation to the Sulfonamides<sup>1</sup>

Roblin, Richard O.; Lampen, J. O.; English, J. P.; Cole, Q. P.; Vaughan, J.

doi:10.1021/ja01218a043

Cited by 207 publications

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“…Thus Roblin, Lampen, English, Cole & Vaughan (1945) found that the triazolo analogues of guanine, adenine and hypoxanthine inhibited growth of Bacterium coli and StaphyZococcus aureus. found guanazolo to be a potent inhibitor of growth of the micro-organism Tetrahymena geleii, and Kidder et al (1949) found it inhibited the growth of malignant cells in mice.…”

Section: Discussionmentioning

confidence: 99%

Chemotherapy and Plant Viruses

Matthews

1953

Journal of General Microbiology

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SUMMARY : When the guanine analogue, 5-amino-7-hydroxy-1-v-triazolo (D) pyrimidine (guanazolo), was sprayed on the leaves of tobacco or Nicotiana glutinosa plants it reduced the number of local lesions and delayed or inhibited systemic spread of lucerne mosaic virus. Guanazolo was more effective when applied before inoculation, but had some effect if applied up to about the second day after inoculation. The compound was more effective in solution in 0.1 yo sodium bicarbonate than in aqueous suspension. With mechanically inoculated plants guanazolo watered on the soil around the plants was less effective than when sprayed on the leaves. Incubated with the virus i n witro the compound did not affect infectivity. In concentrations up to c. 0.005~ guanazolo usually caused negligible plant damage, but a t higher concentrations produced a slight yellowing and distortion in the younger leaves with general stunting if treatments were prolonged.The virus-inhibitory activity of guanazolo was reversed by adenine, guanine and possibly by hypoxanthine, but not by xanthine, uric acid, theobromine, theophylline, caffeine, uracil or thymine.The triazolo analogue of adenine severely damaged plants and had only slight virus inhibitory activity. The hypoxanthine analogue caused no plant damage. It was less effective than guanazolo in tobacco and N. glutinosa but more effective in reducing the number of local lesions produced in beans. Thiouracil, methylthiouracil and propylthiouracil were ineffective against lucerne mosaic virus. Thiouracil caused fairly severe plant damage.Guanazolo had slight or negligible effects on spotted Wilt virus in tomato, potato viruses X and Y in potato, and tobacco and pea mosaic virus in peas. Applied as a leaf spray a t 0 . 0 1~ concentration guanazolo delayed or prevented systemic movement of cucumber mosaic virus from mechanically inoculated cucumber leaves, but had no effect when watered on the soil. However, watering the compound on the soil gave some control when the virus was introduced by aphids.The indirect measures at present used to control plant-virus diseases, such as eliminating sources of infection and developing resistant varieties, are for many diseases only partially effective. The development of compounds which delay or inhibit virus multiplication within the plant could form a basis for a more widely applicable method of control. A variety of compounds, mainly antibiotics, plant-growth substances and dyestuffs, has been tested for possible antivirus activity. Takahashi (1948), using a detached leaf technique, found that malachite green decreased the amount of tobacco mosaic virus produced in Nicotiana glutinosa leaf tissue. Stoddard (1947) stated that the virus causing X disease of peach could be inactivated in living peach buds by soaking buds in solutions of a variety of compounds, and that trees watered or injected with various compounds could be protected against disease. Limasset, Levieil & Sechet (1948) found that 2-methyl-4-chlorophenoxy acetic acid temporarily inhibited t...

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Section: Discussionmentioning

confidence: 99%

Chemotherapy and Plant Viruses

Matthews

1953

Journal of General Microbiology

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“…This nucleobase modification, i.e. the replacement of (C8)H by N [26], was initiated by the more than 50-yearsold discovery of the antibacterial [27] and antitumor [28] properties of 8-azaguanine, which has led to a continued interest in 8-azapurines and related nucleosides [29,30,31,32]. Interestingly, the present study reveals that the metal ion-binding properties of 9,8aPMEA 2À are very similar to those of PMEA 2À whereas the ones of 8,8aPMEA…”

Section: Introductionmentioning

confidence: 99%

Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA)

et al. 2004

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“…Certain modifications of the bases and corresponding nucleosides and nucleotides of ribonucleic acids (RNA) and deoxyribonucleic acids (DNA) have proven to possess very interesting biological and chemotherapeutic properties (Skoda, 1963;Roblin, Lampen, English, Cole & Vaughan, 1945;Kidder, Dewey, Parks & Woodside, 1949;Montgomery, Elliot & Thomas, 1975). The differences in activity between the naturally occurring bases and the modified bases are due in part to the structural changes and in part to the electronic effects brought about by the various modifications.…”

Section: Introduetlonmentioning

confidence: 99%

Pyridazine nucleosides. The structure and conformational analysis of 5-hydroxy-2-(1-β-D-ribofuranosyl)-3(2H)-pyridazinone

Graves¹,

Hodgson²

1981

Acta Crystallogr Sect B

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The crystal structure of the doubly modified nucleoside 5-hydroxy-2-( 1 -fl-D-ribofuranosyl)-3 (2H)-pyridazinone or 3-deaza-6-azauridine (C9HI2N206, M r = 244.206) has been determined using three-dimensional X-ray counter data. The uridine analog crystallizes in the monoelinic space group P21 with two molecules in a unit cell of dimensions a = 7. 136 (7), b = 7.636 (7), c = 10.119 (8) A, and fl= 101.54 (6) °. D O (by flotation in tetrahydrofuran-tribromomethane) = 1.50, De= 1.504 Mg m -3, #(Cu Ka)= 1.06 mm -~. The structure was solved by direct methods and refined by full-matrix least squares using 848 independent data with I > 3a

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Studies in Chemotherapy. VIII. Methionine and Purine Antagonists and their Relation to the Sulfonamides¹

Cited by 207 publications

References 0 publications

Chemotherapy and Plant Viruses

Chemotherapy and Plant Viruses

Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA)

Pyridazine nucleosides. The structure and conformational analysis of 5-hydroxy-2-(1-β-D-ribofuranosyl)-3(2H)-pyridazinone

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Studies in Chemotherapy. VIII. Methionine and Purine Antagonists and their Relation to the Sulfonamides1

Cited by 207 publications

References 0 publications

Chemotherapy and Plant Viruses

Chemotherapy and Plant Viruses

Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA)

Pyridazine nucleosides. The structure and conformational analysis of 5-hydroxy-2-(1-β-D-ribofuranosyl)-3(2H)-pyridazinone

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Studies in Chemotherapy. VIII. Methionine and Purine Antagonists and their Relation to the Sulfonamides¹