Polyamine flux analysis by determination of heavy isotope incorporation from 13C, 15N-enriched amino acids into polyamines by LC-MS/MS

Amino Acids

Volumn 42, Issue 2-3, 2012, Pages 451-460

  Cerrada Gimenez, Marc ^a   Häkkinen, Merja R ^a   Vepsäläinen, Jouko ^a   Auriola, Seppo ^a   Alhonen, Leena ^a   Keinänen, Tuomo A ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

Fetal fibroblasts; LC MS MS; MDL 72527; Polyamine flux; Polyamines; SSAT

Indexed keywords

ACYLTRANSFERASE; AMINO ACID; ARGININE; CARBON 13; METHIONINE; NITROGEN 15; ORNITHINE; POLYAMINE; SPERMIDINE SPERMINE N1 ACETYLTRANSFERASE; UNCLASSIFIED DRUG; CARBON; NITROGEN;

AMINE TRANSPORT; ANIMAL CELL; ARTICLE; CELL LINE; CONTROLLED STUDY; FETUS; LIQUID CHROMATOGRAPHY; METHODOLOGY; MOUSE; NONHUMAN; POLYAMINE TRANSPORT; PRIORITY JOURNAL; PROTEIN EXPRESSION; SEPARATION TECHNIQUE; TANDEM MASS SPECTROMETRY; TIME; ANIMAL; C57BL MOUSE; CALIBRATION; CULTURE MEDIUM; METABOLISM; TRANSGENIC MOUSE; VALIDATION STUDY;

AMINO ACIDS; ANIMALS; BIOGENIC POLYAMINES; CALIBRATION; CARBON ISOTOPES; CHROMATOGRAPHY, LIQUID; CULTURE MEDIA; MICE; MICE, INBRED C57BL; MICE, TRANSGENIC; NITROGEN ISOTOPES; TANDEM MASS SPECTROMETRY;

EID: 84861668845     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-1024-x     Document Type: Article

References (43)

1. Alhonen L, Karppinen A, Uusi-Oukari M, Vujcic S, Korhonen VP, Halmekytö M, Kramer DL, Hine R, Jänne J, Porter CW (1998) Correlation of polyamine and growth repsonses to N1, N11- diethylnorspermine in primare fetal fibroblasts derived from transgenic mice overexepressing spermidine/spermien N1-acetyltransferase. J Biol Chem 273:1964-1969 (Pubitemid 28069241)
2. Babbar N, Murray-Stewart T, Casero RA (2007) Inflammation and polyamine catabolism: the good, the bad and the ugly. Biochem Soc Trans 35:300-304 (Pubitemid 46596495)
3. Bachrach U, Bekierkunst A, Abzug S (1967) The occurrence of putrescine, spermidine and spermine in Ehrlich ascites cells. Isr J Med Sci 3:474-477
4. Balasundaram D, Tyagi AK (1991) Polyamine-DNA nexus: structural ramifications and biological implications. Mol Cell Biochem 100:129-140
5. Casero RA, Marton LJ (2007) Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases. Nat Rev Drug Discov 6:373-390 (Pubitemid 46705201)
6. Cerrada-Gimenez M, Häyrinen J, Juutinen S, Reponen T, Jänne J, Alhonen L (2009) Proteomic analysis of livers from a transgenic mouse line with activated polyamine catabolism. Amino Acids 38:613-622
7. Dezeure F, Sarhan S, Seiler N (1988) Chain-fluorinated polyamines as tumor markers-IV: comparison of 2-fluoroputrescine and 2, 2-difluoroputrescine as substrates of spermidine synthase in vitro and in vivo. Int J Biochem 20:1299-1312 (Pubitemid 19000862)
8. Gerner EW, Meyskens FL (2004) Polyamines and cancer: old molecules, new understanding. Nat Rev Cancer 4:781-792 (Pubitemid 39331150)
9. Gerner EW, Meyskens FL (2009) Combination chemoprevention for colon cancer targeting polyamine synthesis and inflammation. Clin Canc Res 15:758-761
10. Gerner EW, Meyskens FL, Goldschmid S, Lance P, Pelot D (2007) Rationale for, and design of, a clinical trial targeting polyamine metabolism for colon cancer chemoprevention. Amino Acids 33:189-195 (Pubitemid 47222961)
11. Häkkinen MR, Keinänen TA, Vepsäläinen J, Khomutov AR, Alhonen L, Jänne J, Auriola S (2007) Analysis of underivatized polyamines by reversed phase liquid chromatography with electrospray tandem mass spectrometry. J Pharm Biomed Anal 45:625-634 (Pubitemid 350007954)
12. Häkkinen MR, Keinänen TA, Vepsäläinen J, Khomutov AR, Alhonen L, Jänne J, Auriola S (2008) Quantitative determination of underivatized polyamines by using isotope dilution RP-LC-ESIMS/ MS. J Pharm Biomed Anal 48:414-421
13. Häkkinen MR, Keinänen TA, Khomutov AR, Auriola S, Weisell J, Alhonen L, Jänne J, Vepsäläinen J (2009) Synthesis of novel deuterium labelled derivatives of N-alkylated polyamines. Tetrahedron 65:547-562
14. Häkkinen MR, Hyvönen MT, Auriola S, Casero RA, Vepsäläinen J, Khomutov AR, Alhonen L, Keinänen TA (2010) Metabolism of N-alkylated spermine analogues by polyamine and spermine oxidases. Amino Acids 38:369-381
15. Höltta E, Jänne J (1972) Ornithine decarboxylase activity and the accumulation of putrescine at early stages of liver regeneration. Febs Lett 23:117-121
16. Höltta E, Sinervirta R, Jänne J (1971) Synthesis and accumulation of polyamines in rat liver regenerating after treatment with carbon tetrachloride. Biochem Biophys Res Commun 5:350-357
17. Hyvönen T, Keinänen TA, Khomutov AR, Khomutov RM, Eloranta TO (1992) Monitoring of the uptake and metabolism of aminooxy analogues of polyamines in cultured cells by highperformance liquid chromatography. J Chromatogr 574:17-21
18. Hyvönen MT, Merentie M, Uimari A, Keinänen TA, Jänne J, Alhonen L (2007) Mechanisms of polyamine catabolisminduced acute pancreatitis. Biochem Soc Trans 35:326-330 (Pubitemid 46596501)
19. Jänne J, Alhonen L, Pietilä M, Keinänen TA (2004) Genetic approaches to the cellular functions of polyamines in mammals. Eur J Biochem 271:877-894 (Pubitemid 38299643)
20. Jell J, Merali S, Hensen ML, Mazurchuk R, Spernyak JA, Diegelman P, Kisiel ND, Barrero C, Deeb KK, Alhonen L, Patel MS, Porter CW (2007) Genetically altered expression of spermidine/ spermine N1-acetyltransferase affects fat metabolism in mice via acetyl-CoA. J Biol Chem 282:8404-8413 (Pubitemid 47093580)
21. Johnson TD (1996) Modulation of channel function by polyamines. Trends Pharmacol Sci 17:22-27 (Pubitemid 26027737)
22. Kramer D, Stanek J, Diegelman P, Regenass U, Schneider P, Porter CW (1995) Use of 4-fluoro-L-ornithine to monitor metabolic flux through the polyamine biosynthetic pathway. Biochem Pharmacol 50:1433-1443
23. Kramer DL, Diegelman P, Jell J, Vujcic S, Merali S, Porter CW (2008) Polyamine acetylation modulates polyamine metabolic flux, a prelude to broader metabolic consequences. J Biol Chem 283:4241-4251
24. Liu LF, Wang JC (1987) Supercoiling of the DNA template during transcription. Proc Natl Acad Sci USA 84:7024-7027
25. Merentie M, Uimari A, Pietilä M, Sinervirta R, Keinänen TA, Vepsäläinen J, Khomutov A, Grigorenko N, Herzig KH, Jänne J, Alhonen L (2007) Oxidative stress and inflammation in the pathogenesis of activated polyamine catabolism-induced acute pancreatitis. Amino Acids 33:323-330 (Pubitemid 47222968)
26. Meyskens FL, McLaren CE, Pelot D, Fujikawa-Brooks S, Carpenter PM, Hawk E, Kelloff G, Lawson MJ, Kidao J, McCracken J, Albers CG, Ahnen DJ, Turgeon DK, Goldschmid S, Lance P, Hagedorn CH, Gillen DL, Gerner EW (2008) Difluoromethylornithine plus sulindac for the prevention of sporadic colorectal adenomas: a randomized placebo-controlled double-blind trial. Cancer Prev Res 1:32-38
27. Niiranen K, Keinänen TA, Pirinen E, Heikkinen S, Tusa M, Fatrai S, Suppola S, Pietilä M, Uimari A, Laakso M, Alhonen L, Jänne J (2006) Mice with targeted disruption of spermidine/spermine N1- acetyltransferase gene maintain nearly normal tissue polyamine homeostasis but show signs of insulin resistance upon aging. J Cell Mol Med 10:933-945
28. O'Brien TG, Simsiman RC, Boutwell RK (1975) Induction of the polyamine-biosynthetic enzymes in mouse epidermis by tumorpromoting agents. Cancer Res 35:1662-1670
29. Park MH, Cooper HL, Folk JE (1981) Identification of hypusine, an unusual amino acid, in a protein from human lymphocytes and of spermidine as its biosynthetic precursor. PNAS 78:2869-2873
30. Park MH, Nishimura K, Zanelli CF, Valentini SR (2010) Functional significance of eIF5A and its hypusine modification in eukaryotes. Amino Acids 38:491-500
31. Paulus TJ, Davis RH (1983) A double-isotope derivative assay for polyamines. Methods Enzymol 94:36-42 (Pubitemid 13051004)
32. Pirinen E, Kuulasmaa T, Pietilä M, Heikkinen S, Tusa M, Itkonen P, Boman S, Skommer J, Virkamäki A, Hohtola E, Kettunen M, Fatrai S, Kansanen E, Koota S, Niiranen K, Parkkinen J, Levonen AL, Ylä-Herttuala S, Hiltunen JK, Alhonen L, Smith U, Jänne J, Laakso M (2007) Enhanced polyamine catabolism alters homeostatic control of white adipose tissue mass, energy expenditure, and glucose metabolism. Mol Cell Biol 27:4953-4967 (Pubitemid 47016144)
33. Pirinen E, Gylling H, Itkonen P, Yaluri N, Heikkinen S, Pietilä M, Kuulasma T, Tusa M, Cerrada-Gimenez M, Pihlajamäki J, Alhonen L, Jänne J, Miettinen T, Laakso M (2010) Activated polyamine catabolism leads to low cholesterol levels by enhancing bile acid synthesis. Amino Acids 28:549-560
34. Russell DH, McVicker TA (1971) Polyamine metabolism in mouse liver after partial hepatectomy. Biochim Biophys Acta 244:85-93
35. Seiler N, Bolkenius FN, Knödgen B (1985) The influence of catabolic reactions on polyamine excretion. Biochem J 225:219-226 (Pubitemid 15151972)
36. Shiba T, Mizote H, Kaneko T, Nakajima T, Kakimoto Y (1971) Hypusine, a new amino acid occurring in bovine brain: isolation and structural determination. Biochim Biophys Acta 244:523-531
37. Smirnov IV, Dimitrov SI, Makarov VL (1988) Polyamine-DNA interactions: condensation of chromatin and naked DNA. J Biomol Struct Dyn 5:1149-1161
38. Suppola S, Pietilä M, Parkkinen JJ, Korhonen VP, Alhonen L, Halmekytö M, Porter CW, Jänne J (1999) Overexpression of spermidine/spermine N1-acetyltransferase under the control of mouse metallothionein I promoter in transgenic mice: evidence for a striking post-transcriptional regulation of transgene expression by a polyamine analogue. Biochem J 338:311-316
39. Thomas TJ, Bloomfield VA, Canellakis ZN (1985) Differential effects on the B-to-Z transition of poly(dG-me5dC).poly(dGme5dC) produced by N1- and N8-acetyl spermidine. Biopolymers 24:725-729
40. Uemura T, Yerushalmi HF, Tsaprailis G, Stringer DE, Pastorian KE, Hawel L, Byus GV, Gerner EW (2008) Identification and characterization of a diamine exporter in colon epithelial cells. J Biol Chem 283:26428-26435
41. van Nieuwenhove S, Schechter PJ, Declercq J, Boné G, Buekr J, Sjoerdsma A (1985) Treatmetn of gambiense sleeping sickness in the Sudan with oral DFMO (DL-alpha-difluoromethylornithine), an inhibitor of ornithine decarboxylase; first field trial. Trans R Soc Trop Med Hyg 79:692-698 (Pubitemid 16249110)
42. Williams K (1997) Interactions of polyamines with ion channels. Biocheml J 325:289-297 (Pubitemid 27338704)
43. Williams-Ashman HG, Coppoc GL, Weber G (1972) Imbalance in ornithine metabolism in hepatomas of different growth rates as expressed in formation of putrescine, spermidine, and spermine. Cancer Res 32:1924-1932