Chloramphenicol<sup>1</sup> (Chloromycetin). IX. Some Analogs Having Variations of the Acyl Group

Rebstock, Mildred C.

doi:10.1021/ja01166a129

Cited by 19 publications

(9 citation statements)

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“…L( +)-threo isomer of chloramphenicol. The L(+)-threo isomer of chloramphenicol was prepared from L( + ) -threo-1-p-nitro phenyl-2-amino-1, 3-propanediol and methyl dichloracetate by a published procedure (3,11 Chemicals. Chloramphenicol and the precursor of the isomer were generous gifts from Parke-Davis & Co., Sydney, Australia.…”

Section: Methodsmentioning

confidence: 99%

Relationship between Dimorphology and Respiration in Mucor genevensis Studied with Chloramphenicol

Clark-Walker

1973

J Bacteriol

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Growth of Mucor genevensis , a facultatively anaerobic dimorphic mold, in high concentrations of chloramphenicol (4 mg/ml) leads to increased numbers of yeast-like cells and small club-like mycelial forms. This change in morphology is accompanied by a threefold increase in the mass doubling time, the loss of cyanide-sensitive respiration, and the development of cyanide-insensitive respiration. Associated with these changes is the absence of cytochromes aa 3 and b and the inability of the organism to utilize ethanol; in addition, mitochondria appear more numerous and have less internal membrane. A further inhibitory action of the antibiotic, other than eliminating functional mitochondria, appears likely since microaerobic cultures which lack respiratory ability have twice the mass doubling time in the presence of the drug. Although a small inhibition of amino acid incorporation by cytoplasmic ribosomes is found with a high chloramphenicol concentration, it is insufficient to account for the effect on growth of the microaerobic culture. The nature of this additional effect of chloramphenicol remains to be determined, but it has been shown that increasing the glucose concentration can partially reverse this action of the antibiotic. The effect of the drug on the morphology of the organism is not as dramatic as that of phenethyl alcohol in producing yeast-like forms. However, in view of the action of chloramphenicol in eliminating functional mitochondria in M. genevensis the suggestion that phenethyl alcohol exerts its effect in promoting yeast-like morphology by uncoupling oxidative phosphorylation should be re-examined.

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Section: Methodsmentioning

confidence: 99%

Relationship between Dimorphology and Respiration in Mucor genevensis Studied with Chloramphenicol

Clark-Walker

1973

J Bacteriol

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“…The compounds used in these investigations were prepared synthetically and consisted of the DL threo racemic mixtures unless otherwise indicated. The synthetic methods employed have been described previously by Controulis, Rebstock, and Crooks (1949), Long and Troutman (1949a, b), Rebstock, Crooks, Controulis, and Bartz (1949), and Rebstock (1950).…”

Section: Methodsmentioning

confidence: 99%

Reduction of Chloromycetin and Related Compounds by Escherichia Coli

Smith

Worrel

1953

J Bacteriol

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“…Although these studies have so far failed to provide any definite idea about the exact structural component responsible for the activity, the dichloroacetamide (-NHCOCHC12) group appears to play an important role in the biological activity of the antibiotic. The replacement of the dichloroacetyl group (-COCHC12) with various acyl or aryl groups leads to 0108-2701/84/111972-03501.50 © 1984 International Union of Crystallography some interesting findings (Rebstock, 1950). The present paper deals with the structure of 4'-amino-2,2,3'trichloroacetophenone, a structural analogue of chloramphenicol.…”

Section: Cor-3441mentioning

confidence: 98%

Structure of 4'-amino-2,2,3'-trichloracetophenone, C8H6Cl3NO

De¹

1984

Acta Crystallogr C

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Chloramphenicol¹ (Chloromycetin). IX. Some Analogs Having Variations of the Acyl Group

Cited by 19 publications

References 0 publications

Relationship between Dimorphology and Respiration in Mucor genevensis Studied with Chloramphenicol

Relationship between Dimorphology and Respiration in Mucor genevensis Studied with Chloramphenicol

Reduction of Chloromycetin and Related Compounds by Escherichia Coli

Structure of 4'-amino-2,2,3'-trichloracetophenone, C8H6Cl3NO

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Chloramphenicol1 (Chloromycetin). IX. Some Analogs Having Variations of the Acyl Group

Cited by 19 publications

References 0 publications

Relationship between Dimorphology and Respiration in Mucor genevensis Studied with Chloramphenicol

Relationship between Dimorphology and Respiration in Mucor genevensis Studied with Chloramphenicol

Reduction of Chloromycetin and Related Compounds by Escherichia Coli

Structure of 4'-amino-2,2,3'-trichloracetophenone, C8H6Cl3NO

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Chloramphenicol¹ (Chloromycetin). IX. Some Analogs Having Variations of the Acyl Group