A cyclic imine intermediate in the in vitro metabolic conversion of 1,6-diaminohexane to 6-aminohexanoic acid and caprolactam

References

• Bachrach U., Abzug S., Bekierkunst A. Cytotoxic effect of oxidized spermine on Ehrlich ascites cells. Biochimica et Biophysica Acta 1967; 134: 174–181
   Web of Science ®Google Scholar
• Brandange S., Lindblom L. The enzyme “aldehyde oxidase” is an iminium oxidase. Reaction with nicotine Δ1′(5′)iminium ion. Biochemical and Biophysical Research Communications 1979; 91: 991–996
   PubMed Web of Science ®Google Scholar
• Brandange S., Eriksson L. H., Rodriquez B. Ring-chain tautomerism of an N, N-acetal formed by enzymatic oxidation of spermine or spermidine. Acta Chemica Scandinavica 1984; B38: 526–528
   Google Scholar
• Callery P. S., Geelhaar L. A. Biosynthesis of 5-aminopentanoic acid and 2-piperidone from cadaverine and 1-piperideine in mouse. Journal of Neurochemistry 1984; 43: 1631–1634
   PubMed Web of Science ®Google Scholar
• Callery P. S., Nayar M. S. B., Geelhaar L. A., Stogniew M., Jakubowski E. M. Applications of deuterium labeling in the study of the in vitro conversion of Δ1-pyrroline to 4-aminobutanoic acid and 2-pyrrolidinone. Biomedical Mass Spectrometry 1980; 7: 525–528
   PubMedGoogle Scholar
• Callery P. S., Geelhaar L. A., Nayar M. S. B., Stogniew M., Rao K. G. Pyrrolines as prodrugs of γ-aminobutyric acid analogues. Journal of Neurochemistry 1982; 38: 1063–1067
   PubMed Web of Science ®Google Scholar
• Callery P. S., Nayar M. S. B., Geelhaar L. A. Putrescine metabolism: Enzymatic formation and non-enzymatic isotope exchange of Δ1-pyrroline. Biomedical Mass Spectrometry 1984; 11: 118–120
   PubMedGoogle Scholar
• Callery P. S., Egorin M. J., Geelhaar L. A., Nayar M. S. B. Identification of metabolites of the cell-differentiating agent hexamethylene bisacetamide in humans. Cancer Research 1986; 46: 4900–4903
   PubMed Web of Science ®Google Scholar
• Chun H. G., Leyland-Jones B., Hoth D., Shoemaker D., Wolpert-DeFillipes M., Grieshaber C, Cradock J., Davignon P., Moon R., Rifkind R., Wittes R. E. Hexamethylene bisacetamide: a polar-planar compound entering trials as a differentiating agent. Cancer Treatment Reports 1986; 70: 991–996
   PubMedGoogle Scholar
• Claxton G. P., Allen L., Grisar J. M. 2, 3, 4, 5-Tetrahydropyridine. Organic Syntheses. John Wiley and Sons, Inc., New York 1977; 56: 118–122
   Google Scholar
• Conley B. A., Callery P. S., Egorin M. J., Subramanyam B., Geelhaar L. A., Pan S. Involvement of monoamine oxidase and diamine oxidase in the metabolism of the cell differentiating agent hexamethylene bisacetamide (HMBA). Life Sciences 1988; 43: 793–800
   PubMed Web of Science ®Google Scholar
• Egorin M. J., Sigman L. M., Van Echo D. A., Forrest A., Whitacre M. Y., Aisner J. Phase I clinical and pharmacokinetic study of hexamethylene bisacetamide (NSC95580) administered as a five-day continuous infusion. Cancer Research 1987; 47: 617–623
   PubMed Web of Science ®Google Scholar
• Felsted R. L., Chaykin S. N1-Methylnicotinamide oxidation in a number of mammals. Journal of Biological Chemistry 1967; 242: 1274–1279
   PubMed Web of Science ®Google Scholar
• Fenselau C., Lehman J. P., Myles A., Brandt J., Yost G. S., Friedman O. M., Colvin M. Iminocyclophosphamide as a chemically reactive metabolite of cyclophosphamide. Drug Metabolism and Disposition 1982; 10: 636–640
   PubMed Web of Science ®Google Scholar
• Gaugas J. M., Dewey D. L. Hog kidney diamine oxidase conversion of biogenic diamines to inhibitors of cell proliferation. Journal of Pathology 1981; 134: 243–252
   PubMed Web of Science ®Google Scholar
• Gross P. Biological activity of π-caprolactam. CRC Critical Reviews 1984; 13: 205–216
   Google Scholar
• Hall W. W., Krenitsky T. A. Aldehyde oxidase from rabbit liver: Specificity toward purines and their analogs. Archives of Biochemistry and Biophysics 1986; 251: 36–46
   PubMed Web of Science ®Google Scholar
• Hasse K., Maisack H. Die reaktionsprodukte der enzymatischen oxydation von putrescin und cadaverin. Biochemische Zeitschrift 1955; 327: 296–304
   PubMedGoogle Scholar
• Hasse K., Maisack H. Δ1-Aza-cyclohepten, ein enzymatisches oxydationsprodukt von hexamethylendiamin. Biochemische Zeitschrift 1957; 328: 429–432
   PubMedGoogle Scholar
• Knox W. E. The quinine-oxidizing enzyme and liver aldehyde oxidase. Journal of Biological Chemistry 1946; 163: 699–711
   PubMed Web of Science ®Google Scholar
• Lundgren D. W., Lloyd H. A., Hankins J. Δ1-Pyrroline: An intermediary metabolite in the conversion of putrescine to 2-pyrrolidone. Biochemical and Biophysical Research Communications 1980; 97: 667–672
   PubMed Web of Science ®Google Scholar
• Mann P. J. G., Smithies W. R. Plant enzyme reactions leading to the formation of heterocyclic compounds. Biochemical Journal 1955; 61: 89–100
   PubMed Web of Science ®Google Scholar
• March J. Advanced Organic Chemistry, 3rd Edition. Wiley-Interscience, New York 1985; 370
   Google Scholar
• Pegg A. E. Recent advances in the biochemistry of polyamines in eukaryotics. Biochemical Journal 1986; 234: 249–262
   PubMed Web of Science ®Google Scholar
• Rajagopalan K. V., Handler P. Hepatic aldehyde oxidase III. The substrate-binding site. Journal of Biological Chemistry 1964; 239: 2027–2035
   PubMed Web of Science ®Google Scholar
• Rajagopalan K. V., Handler P. Aldehyde oxidase. Methods in Enzymology 1966; 9: 364–368
   Google Scholar
• Reuben R. C., Khanna P. L., Gazitt Y., Breslow R., Rifkind R. A. Inducers of erythroleukemic differentiation. Relationships of structure to activity among polar-planar compounds. Journal of Biological Chemistry 1978; 253: 4214–4218
   PubMed Web of Science ®Google Scholar
• Rowinsky E. K., Ettinger D. S., Growchow L. S., Brundrett R. B., Cates A. E., Donehower R. C. Phase I and pharmacologic study of hexamethylene bisacetamide in patients with advanced cancer. Journal of Clinical Oncology 1986; 4: 1835–1844
   PubMed Web of Science ®Google Scholar
• Schopf V. C., Komzak A., Braum F., Jacobi E. Uber die polymeren des Δ1-piperideins. Justus Liebigs Annalen Der Chemie 1948; 559: 1–42
   Google Scholar
• Snyder S. W., Eggrin M. J., Geelhaar L. A., Hamburger A. W., Callery P. S. Induction of differentiation of human promyelocytic leukemia cells (HL60) by metabolites of hexamethylene bisacetamide. Cancer Research 1988; 48: 3613–3616
   PubMed Web of Science ®Google Scholar
• Stephenson N. R. The oxidative deamination of diamines by histaminase. Journal of Biological Chemistry 1943; 149: 169–176
   Google Scholar
• Taylor S. M., Stubley-Beedham C., Stell J. G. P. Simultaneous formation of 2-and 4-quinolones from quinolinium cations catalysed by aldehyde oxidase. Biochemical Journal 1984; 220: 67–74
   PubMed Web of Science ®Google Scholar
• Zeller E. A., Stern R., Wenk M. Uber die diaminoxydase-reaktion. Helvetica Chimica Acta 1940; 23: 3–17
   Google Scholar