Abstract
Schiff bases of the diamines 1,3-diaminopropane, putrescine, and cadaverine and the polyamines spermidine and spermine with pyridoxal or pyridoxal phosphate occur in human urine, as shown by gas chromatographic/mass spectrometric selected ion-monitoring techniques. By use of synthetic standards, procedures were devised for conversion of the Schiff bases to stable derivatives amenable to gas chromatographic/mass spectrometric analysis. These procedures involve borohydride reduction of the C = N double bond, hydrolytic removal of the phosphate group, chromatographic separation from the bulk of urinary constituents, and trifluoroacetylation of polar functional groups. The levels of the polyamine-pyridoxal Schiff bases were estimated to be in the range of pmol/ml or urine.
Full text
PDF



Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Bartos F., Bartos D., Grettie D. P., Campbell R. A. Polyamine levels in normal human serum. Comparison of analytical methods. Biochem Biophys Res Commun. 1977 Apr 25;75(4):915–919. doi: 10.1016/0006-291x(77)91469-3. [DOI] [PubMed] [Google Scholar]
- Bosron W. F., Veitch R. L., Lumeng L., Li T. K. Subcellular localization and identification of pyridoxal 5'-phosphate-binding proteins in rat liver. J Biol Chem. 1978 Mar 10;253(5):1488–1492. [PubMed] [Google Scholar]
- Dobbelstein H., Körner W. F., Mempel W., Grosse-Wilde H., Edel H. H. Vitamin B6 deficiency in uremia and its implications for the depression of immune responses. Kidney Int. 1974 Mar;5(3):233–239. doi: 10.1038/ki.1974.28. [DOI] [PubMed] [Google Scholar]
- Heller J. S., Canellakis E. S., Bussolotti D. L., Coward J. K. Stable multisubstrate adducts as enzyme inhibitors. Potent inhibition of ornithine decarboxylase by N-(5'-phosphopyridoxyl)-ornithine. Biochim Biophys Acta. 1975 Sep 22;403(1):197–207. doi: 10.1016/0005-2744(75)90022-4. [DOI] [PubMed] [Google Scholar]
- Lumeng L., Ryan M. P., Li T. K. Validation of the diagnostic value of plasma pyridoxal 5'-phosphate measurements in vitamin B6 nutrition of the rat. J Nutr. 1978 Apr;108(4):545–553. doi: 10.1093/jn/108.4.545. [DOI] [PubMed] [Google Scholar]
- Nandi D. L. Delta-aminolevulinic acid synthase of rhodopseudomonas spheroides. Binding of pyridoxal phosphate to the enzyme. Arch Biochem Biophys. 1978 Jun;188(2):266–271. doi: 10.1016/s0003-9861(78)80008-3. [DOI] [PubMed] [Google Scholar]
- Nishioka K., Romsdahl M. M. Elevation of putrescine and spermidine in sera of patients with solid tumors. Clin Chim Acta. 1974 Dec 2;57(2):155–161. doi: 10.1016/0009-8981(74)90424-0. [DOI] [PubMed] [Google Scholar]
- O'Leary M. H. A proposed structure for the 330 -nm chromophore of glutamate decarboxylase and other pyridoxal 5'-phosphate dependent enzymes. Biochim Biophys Acta. 1971 Aug 20;242(2):484–492. doi: 10.1016/0005-2744(71)90241-5. [DOI] [PubMed] [Google Scholar]
- Rosenblum M. G., Durie B. G., Beckerman R. C., Taussig L. M., Russell D. H. Cystic fibrosis: decreased conjugation and excretion of [14C]spermidine. Science. 1978 Jun 30;200(4349):1496–1497. doi: 10.1126/science.663632. [DOI] [PubMed] [Google Scholar]
- Rosenblum M. G., Russell D. H. Conjugation of radiolabeled polyamines in the rat. Cancer Res. 1977 Jan;37(1):47–51. [PubMed] [Google Scholar]
- Russell D. H., Levy C. C., Schimpff S. C., Hawk I. A. Urinary polyamines in cancer patients. Cancer Res. 1971 Nov;31(11):1555–1558. [PubMed] [Google Scholar]
- Smith R. G., Bartos D., Bartos F., Grettie D. P., Frick W., Campbell R. A., Daves G. D., Jr 1-N-Acetylspermidine: occurrence in normal human serum. Biomed Mass Spectrom. 1978 Sep;5(9):515–517. doi: 10.1002/bms.1200050902. [DOI] [PubMed] [Google Scholar]
- Smith R. G., Daves G. D., Jr Gas chromatography mass spectrometry analysis of polyamines using deuterated analogs as internal standards. Biomed Mass Spectrom. 1977 Jun;4(3):146–151. doi: 10.1002/bms.1200040305. [DOI] [PubMed] [Google Scholar]
- Snell E. E. Analogs of pyridoxal or pyridoxal phosphate: relation of structure to binding with apoenzymes and to catalytic activity. Vitam Horm. 1970;28:265–290. doi: 10.1016/s0083-6729(08)60897-3. [DOI] [PubMed] [Google Scholar]
- Tabor H., Tabor C. W., Irreverre F. Quantitative determination of aliphatic diamines and polyamines by an automated liquid chromatography procedure. Anal Biochem. 1973 Oct;55(2):457–467. doi: 10.1016/0003-2697(73)90136-x. [DOI] [PubMed] [Google Scholar]
- Tsuji M., Nakajima T., Sano I. Putrescine, spermidine, N-acetylspermidine and spermine in the urine of patients with leukaemias and tumors. Clin Chim Acta. 1975 Mar 10;59(2):161–167. doi: 10.1016/0009-8981(75)90024-8. [DOI] [PubMed] [Google Scholar]
- WACHSTEIN M., KELLNER J. D., ORTIZ J. M. Pyridoxal phosphate in plasma and leukocytes in patients with leukemia and other diseases. Proc Soc Exp Biol Med. 1960 Dec;105:563–566. doi: 10.3181/00379727-105-26177. [DOI] [PubMed] [Google Scholar]
