Abstract
The prophage-inducing capability of hydroxylamine sulfate and 36 of its derivatives, and of hydrazine dihydrochloride and dihydrazine sulfate and 43 of their derivatives, was determined in Escherichia coli W1709 (λ). Maximal nontoxic concentrations up to 1 mg/ml were tested. Hydroxylamine sulfate was active at 2.5 μg/ml and the following 17 derivatives were active at concentrations ranging up to 500 μg/ml: α-naphthylhydroxylamine, N-hydroxy-2-aminofluorene, oxamyl hydroxamic acid, O-carbamoyl hydroxylamine (isohydroxyurea), N-hydroxyurethane, N-methylhydroxylamine HCl, salicylhydroxamic acid, oxalohydroxamic acid, methoxyamine HCl, ethoxyamine HCl, N, N-diethylhydroxylamine oxalate, formaldoxime, formamidoxime, acetohydroxamic acid, acetaldoxime, acetone oxime, and hydroxyguanidine sulfate. Hydrazine dihydrochloride and dihydrazine sulfate were effective inducers at 5.0 and 2.5 μg/ml, respectively, and the following nine derivatives of them were active at concentrations ranging up to 500 μg/ml: phthalic acid hydrazide, phenylhydrazine HCl, p-nitrophenylhydrazine, p-chlorophenylhydrazine HCl, formylhydrazine, carbohydrazide, semicarbazide HCl, 1-methyl-1-phenyl-hydrazine sulfate, and acetic acid hydrazide. Nineteen hydroxylamine and 34 hydrazine derivatives were ineffective as inducers. Application of the prophage-induction system as a tool for detection of responsive hydroxylamino and hydrazino compounds which may be potential toxicological hazards in the environment is discussed.
Full text
PDF





Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- ADAMSON R. H. ACTIVITY OF CONGENERS OF HYDROXYUREA AGAINST ADVANCED LEUKEMIA L1210. Proc Soc Exp Biol Med. 1965 Jun;119:456–458. doi: 10.3181/00379727-119-30209. [DOI] [PubMed] [Google Scholar]
- BERENBLUM I., BEN-ISHAI D., HARAN-GHERA N., LAPIDOT A., SIMON E., TRAININ N. Skin initiating action and lung carcinogenesis byderivatives of urethane (ethyl carbamate) and related compounds. Biochem Pharmacol. 1959 Sep;2:168–176. doi: 10.1016/0006-2952(59)90065-6. [DOI] [PubMed] [Google Scholar]
- BERNHEIM M. L. THE ENZYMIC HYDROLYSIS OF CERTAIN HYDROXAMIC ACIDS. Arch Biochem Biophys. 1964 Aug;107:313–318. doi: 10.1016/0003-9861(64)90336-4. [DOI] [PubMed] [Google Scholar]
- BIANCIFIORI C., BUCCIARELLI E., CLAYSON D. B., SANTILLI F. E. INDUCTION OF HEPATOMAS IN CBA-CB-SE MICE BY HYDRAZINE SULPHATE AND THE LACK OF EFFECT OF CROTON OIL ON TUMOUR INDUCTION IN BALB-C-CB-SE MICE. Br J Cancer. 1964 Sep;13:543–550. doi: 10.1038/bjc.1964.62. [DOI] [PMC free article] [PubMed] [Google Scholar]
- BIANCIFIORI C., RIBACCHI R. Pulmonary tumours in mice induced by oral isoniazid and its metabolites. Nature. 1962 May 5;194:488–489. doi: 10.1038/194488a0. [DOI] [PubMed] [Google Scholar]
- BORENFREUND E., KRIM M., BENDICH A. CHROMOSOMAL ABERRATIONS INDUCED BY HYPONITRITE AND HYDROXYLAMINE DERIVATIVES. J Natl Cancer Inst. 1964 Mar;32:667–679. [PubMed] [Google Scholar]
- Boyland E., Nery R., Peggie K. S. The induction of chromosome aberrations in Vicia faba root meristems by N-hydroxyurethane and related compounds. Br J Cancer. 1965 Dec;19(4):878–882. doi: 10.1038/bjc.1965.102. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Chaube S., Murphy M. L. The effects of hydroxyurea and related compounds on the rat fetus. Cancer Res. 1966 Jul;26(7):1448–1457. [PubMed] [Google Scholar]
- Cohen S. M., Ertürk E., Price J. M., Bryan G. T. Comparative carcinogenicity in the rat of 2-hydrazinothiazoles with nitrofuryl, nitrophenyl, or aminophenyl substituents in the 4-position. Cancer Res. 1970 Apr;30(4):897–901. [PubMed] [Google Scholar]
- Epstein S. S., Saporoschetz I. B. On the association between lysogeny and carcinogenicity in nitroquinolines and related compounds. Experientia. 1968 Dec 15;24(12):1245–1248. doi: 10.1007/BF02146650. [DOI] [PubMed] [Google Scholar]
- FEDOROV M. V. Chastichnoe otvlechenie produktov fiksatsii molekuliarnogo azota iz kletok azotobaktera v pitatel-nuiu sredu. Mikrobiologiia. 1952 Jul-Aug;21(4):395–405. [PubMed] [Google Scholar]
- FREESE E. B., FREESE E. TWO SEPARABLE EFFECTS OF HYDROXYLAMINE ON TRANSFORMING DNA. Proc Natl Acad Sci U S A. 1964 Nov;52:1289–1297. doi: 10.1073/pnas.52.5.1289. [DOI] [PMC free article] [PubMed] [Google Scholar]
- FREESE E., BAUTZ-FREESE E., BAUTZ E. Hydroxylamine as a mutagenic and inactivating agent. J Mol Biol. 1961 Apr;3:133–143. doi: 10.1016/s0022-2836(61)80040-5. [DOI] [PubMed] [Google Scholar]
- Fishbein W. N., Carbone P. P., Hochstein H. D. Acetohydroxamate: bacterial urease inhibitor with therapeutic potential in hyperammonaemic states. Nature. 1965 Oct 2;208(5005):46–48. doi: 10.1038/208046a0. [DOI] [PubMed] [Google Scholar]
- Heinemann B., Howard A. J., Hollister Z. J. Application of paper chromatograms to the study of inducers of lambda bacteriophage in Escherichia coli. Appl Microbiol. 1967 Jul;15(4):723–725. doi: 10.1128/am.15.4.723-725.1967. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Kriek E. On the interaction of N-2-fluorenylhydroxylamine with nucleic acids in vitro. Biochem Biophys Res Commun. 1965 Sep 22;20(6):793–799. doi: 10.1016/0006-291x(65)90088-4. [DOI] [PubMed] [Google Scholar]
- LEIN J., HEINEMANN B., GOUREVITCH A. Induction of lysogenic bacteria as a method of detecting potential antitumour agents. Nature. 1962 Nov 24;196:783–784. doi: 10.1038/196783a0. [DOI] [PubMed] [Google Scholar]
- LEVENBERG B. ISOLATION AND STRUCTURE OF AGARITINE, A GAMMA-GLUTAMYL-SUBSTITUTED ARYLHYDRAZINE DERIVATIVE FROM AGARICACEAE. J Biol Chem. 1964 Jul;239:2267–2273. [PubMed] [Google Scholar]
- LINGENS F. ERZEUGUNG BIOCHEMISCHER MANGELMUTANTEN VON ESCHERICHIA COLI MIT HILFE VON HYDRAZIN UND HYDRAZINDERIVATEN. Z Naturforsch B. 1964 Feb;19:151–156. [PubMed] [Google Scholar]
- Lijinsky W., Epstein S. S. Nitrosamines as environmental carcinogens. Nature. 1970 Jan 3;225(5227):21–23. doi: 10.1038/225021a0. [DOI] [PubMed] [Google Scholar]
- MILLER E. C., MILLER J. A., HARTMANN H. A. N-Hydroxy-2-acetylaminofluorene: a metabolite of 2-acetylaminofluorene with increased carcinogenic activity in the rat. Cancer Res. 1961 Jul;21:815–824. [PubMed] [Google Scholar]
- Magee P. N., Barnes J. M. Carcinogenic nitroso compounds. Adv Cancer Res. 1967;10:163–246. doi: 10.1016/s0065-230x(08)60079-2. [DOI] [PubMed] [Google Scholar]
- Miller J. A., Miller E. C. The metabolic activation of carcinogenic aromatic amines and amides. Prog Exp Tumor Res. 1969;11:273–301. doi: 10.1159/000391399. [DOI] [PubMed] [Google Scholar]
- Mirvish S. S. The carcinogenic action and metabolism of urethan and N-hydroxyurethan. Adv Cancer Res. 1968;11:1–42. doi: 10.1016/s0065-230x(08)60386-3. [DOI] [PubMed] [Google Scholar]
- Neilands J. B. Hydroxamic acids in nature. Science. 1967 Jun 16;156(3781):1443–1447. doi: 10.1126/science.156.3781.1443. [DOI] [PubMed] [Google Scholar]
- PRICE K. E., BUCK R. E., LEIN J. SYSTEM FOR DETECTING INDUCERS OF LYSOGENIC ESCHERICHIA COLI W1709 (LAMBDA) AND ITS APPLICABILITY AS A SCREEN FOR ANTINEOPLASTIC ANTIBIOTICS. Appl Microbiol. 1964 Sep;12:428–435. doi: 10.1128/am.12.5.428-435.1964. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Perez G., Radomski J. L. The mutagenicity of the N-hydroxy naphthylamines in relation to their carcinogenicity. Ind Med Surg. 1965 Sep;34(9):714–716. [PubMed] [Google Scholar]
- Rosenkranz H. S., Pollak R. D., Schmidt R. M. Biologic effects of isohydroxyurea. Cancer Res. 1969 Jan;29(1):209–218. [PubMed] [Google Scholar]
- SOMERS C. E., HSU T. C. Chromosome damage induced by hydroxylamine in mammalian cells. Proc Natl Acad Sci U S A. 1962 Jun 15;48:937–943. doi: 10.1073/pnas.48.6.937. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Stoll R., Bodit F., Maraud R. Sur l'action de divers antimitotiques apparentés à l'hydroxyurée et à la semicarbazide chez l'embryon de Poulet. C R Seances Soc Biol Fil. 1967;161(10):1963–1967. [PubMed] [Google Scholar]
- TOIDA I. Isoniazid-hydrolyzing enzyme of mycobacteria. Am Rev Respir Dis. 1962 May;85:720–726. doi: 10.1164/arrd.1962.85.5.720. [DOI] [PubMed] [Google Scholar]
- Tarnowski G. S., Kreis W., Schmid F. A., Cappuccino J. G., Burchenal J. H. Effect of hydroxylamine (NSC-26250) and related compounds on growth of transplanted animal tumors. Cancer Res. 1966 Nov;26(2 Pt 2):1279–1301. [PubMed] [Google Scholar]
