Über einen Antagonisten des Lactoflavins

Kühn, Richard; Weygand, Friedrich; Möller, Ernst Friedrich

doi:10.1002/cber.19430761017

Cited by 47 publications

(11 citation statements)

References 8 publications

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“…On the basis of mixed-crystal formation between methyl-and chloro-substituted compounds in the benzene series, Kuhn, Weygand, and Moller (209) When the redox potentials of the vitamin and antivitamin were compared, it was found that the dihydro derivative of dichloroflavin was a considerably weaker reducing agent. At pH 7 the values were: With L. casei Foster (129) was unable to demonstrate any growth inhibition with isoriboflavin, even when it was tested at 100,000 times the concentration of riboflavin.…”

Section: Ribojlawinmentioning

confidence: 99%

Metabolite Antagonists.

Roblin¹

1946

Chem. Rev.

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Section: Ribojlawinmentioning

confidence: 99%

Metabolite Antagonists.

Roblin¹

1946

Chem. Rev.

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“…This value is in agreement with published data. 8,20 In summary, we have described a more efficient and faster protocol than previous methods for the synthesis of 7,8-dichlororiboflavin.…”

mentioning

confidence: 97%

“…In particular, antibiotic activity has been studied for analogs that induce growth inhibition for several microorganisms. [8][9][10] Flavin analogs are also extensively used to alter or enhance molecular processes of catalysis by flavoproteins. More precisely, those variants are used to analyze cofactor-enzyme covalent binding, molecular oxygen activation, enantioselectivity, semiquinone intermediate formation or photochemical properties of flavins or flavoproteins.…”

mentioning

confidence: 99%

“…Like various other riboflavin analogs that are substituted in positions 7 or 8, it is classically synthesized as described by Kuhn and coworkers. 8 This synthesis is a five-step protocol with a rather low yield, based on monoribitylation of a di-substituted dinitrophenylene with ribamine, followed by catalyzed hydrogenation of the remaining nitro group. Ribamine must first be synthesized by reacting ribose with ammonia at high pressure and temperature.…”

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confidence: 99%

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A two-step synthesis of 7,8-dichloro-riboflavin with high yield

et al. 2012

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“…Eighteen gin. of 1,2-dichloro-4, 5-dinitrobenzene (15) was suspended in 120 cc. of concentrated HCI, the mixture was heated on a steam bath, and 30 gin.…”

mentioning

confidence: 99%

Selective Toxicity of 1,2-Dichloro-4,5-Diaminobenzene: Its Relation to Requirements for Riboflavin and Vitamin B12

Woolley

1951

Journal of Experimental Medicine

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Recent investigations have indicated that one way in which to achieve selectively toxic antimetabolites is to find a biological precursor of a vitamin, and then to construct a suitable analog of it. Such an analog may then harm those species which synthesize this vitamin, and should not affect those which have a nutritional requirement for it. Thus, the selective toxicity of sulfanilamide and its congeners for certain bacteria in contrast to higher animals has been postulated to reside in the difference in requirement for folic acid (1-3). This postulate has received support in the finding that the harmful action of a pimelic acid analog could be foretold with fair precision from a knowledge of nutritional requirements for biotin (4). The vitamin which arises from the precursor by a series of biosynthetic reactions (e.g., biotin) sometimes may be able completely and non-competitively to erase the effects of the analog.The present investigation was undertaken with two questions in mind. (a) Could additional substances of predictable selective toxicity be realized by construction of structural analogs of a precursor of another vitamin? (b) Could a means be found to foretell antimetabolites of the precursor which would not be counteracted by the vitamin?With regard to the first question, the correlation of the selective toxicity of sulfanilamide and of the pimelic acid analog with nutritional requirements for the vitamins, folic acid or biotin, was just cited. In the present study a single precursor of both riboflavin and vitamin B~2 was sought, an analog of this precursor was prepared, and it has been shown to retard the growth of all species examined except those with a nutritional need for these two vitamins. This demonstration added evidence in favor of the postulate that selectively toxic substances can be achieved in this general way.The bearing of the second question on some of the problems of chemotherapy and of pharmacology can be seen from consideration of the action of sulfanilamide, in contrast to that of the pimelic acid analog mentioned above. This

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Über einen Antagonisten des Lactoflavins

Cited by 47 publications

References 8 publications

Metabolite Antagonists.

Metabolite Antagonists.

A two-step synthesis of 7,8-dichloro-riboflavin with high yield

Selective Toxicity of 1,2-Dichloro-4,5-Diaminobenzene: Its Relation to Requirements for Riboflavin and Vitamin B12

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