LC–MS/MS quantification of asymmetric dimethyl arginine and symmetric dimethyl arginine in plasma using surrogate matrix and derivatization with fluorescamine

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References

• 1. Bedford MT. Arginine methylation at a glance. J. Cell Sci. 120(24), 4243–4246 (2007). • Describes arginine methylation by protein arginine methyltransferases.
  Medline CASGoogle Scholar
• 2. Fulton MD, Brown T, Zheng YG. The biological axis of protein arginine methylation and asymmetric dimethylarginine. Int. J. Mol. Sci. 20(13), 3322 (2019). • Describes arginine methylation and asymmetric dimethyl arginine (ADMA) biology.
  CASGoogle Scholar
• 3. Palmer RMJ, Ashton DS, Moncada S. Vascular endothelial cells synthesize nitric oxide from L-arginine. Nature 333, 664–666 (1988).
  Medline CASGoogle Scholar
• 4. Vallance P, Leone A, Calver A, Collier J, Moncada S. Accumulation of an endogenous inhibitor of nitric oxide synthesis in chronic renal failure. Lancet 339, 572–575 (1992).
  Medline CASGoogle Scholar
• 5. Closs EI, Basha FZ, Habermeier A, Forstermann U. Interference of L-Arginine analogues with L-Arginine transport mediated by y⁺ carrier hCAT – 2B. Nitric Oxide. 1(1), 65–73 (1997).
  Medline CASGoogle Scholar
• 6. Maas R. Pharmacotherapies and their influence on asymmetric dimethylarginine (ADMA). Vascular Medicine. 10, S49–S57 (2005).
  MedlineGoogle Scholar
• 7. Ueda S, Yamagishi S, Kaida Y, Okuda S. Asymmetric dimethylarginine may be a missing link between cardiovascular disease and chronic kidney disease. Nephrology. 12, 582–590 (2007).
  Medline CASGoogle Scholar
• 8. Bode-Boger SM, Boger RH, Galland A, Tsikas D, Frolich JC. L-arginine-induced vasodilation in healthy humans: pharmacokinetic-pharmacodynamic relationship. Br. J. Clin. Pharmacol. 46, 489–497 (1998).
  Medline CASGoogle Scholar
• 9. Pettersson A, Hedner T, Milsom I. Increased circulating concentrations of asymmetric dimethyl arginine (ADMA), an endogenous inhibitor of nitric oxide synthesis, in preeclampsia. Acta Obstet. Gynecol. Scand. 77, 808–813 (1998).
  Medline CASGoogle Scholar
• 10. Surdacki A, Nowicki M, Sandmann J, Tsikas D et al. Reduced urinary excretion of nitric oxide metabolites and increased plasma levels of asymmetric dimethylarginine in men with essential hypertension. J. Cardiovasc. Pharmacol. 33, 652–658 (1999).
  Medline CASGoogle Scholar
• 11. Abbasi F, Asagmi T, Cooke JP et al. Plasma concentrations of asymmetric dimethylarginine are increased in patients with type 2 diabetes mellitus. Am. J. Cardiol. 88, 1201–1203 (2001).
  Medline CASGoogle Scholar
• 12. Gorenflo M, Zheng C, Werle E, Fiehn W, Ulmer HE. Plasma levels of asymmetrical dimethyl-L-arginine in patients with congenital heart disease and pulmonary hypertension. J. Cardiovasc. Pharmacol. 37, 489–492 (2001).
  Medline CASGoogle Scholar
• 13. Antoniades C, Shirodaria C, Leeson P et al. Association of plasma asymmetrical dimethylarginine (ADMA) with elevated vascular superoxide production and endothelial nitric oxide synthase uncoupling: implications for endothelial function in human atherosclerosis. Eur. Heart J. 30, 1142–1150 (2009).
  Medline CASGoogle Scholar
• 14. Boger RH. Asymmetric dimethylarginine (ADMA): a novel risk marker in cardiovascular medicine and beyond. Ann. Med. 38, 126–136 (2006).
  MedlineGoogle Scholar
• 15. Boger RH, Maas R, Schulze F, Schwedhelm E. Asymmetric dimethylarginine (ADMA) as a prospective marker of cardiovascular disease and mortality-an update on patient populations with a wide range of cardiovascular risk. Pharmacol. Res. 60, 481–487 (2009).
  MedlineGoogle Scholar
• 16. Fliser D, Kronenberg F, Kielstein JT et al. Asymmetric dimethylarginine and progression of chronic kidney disease: the mild to moderate kidney disease study. J. Am. Soc. Nephrol. 16, 2456–2461 (2005).
  Medline CASGoogle Scholar
• 17. Tain Y, Hsu C. Toxic dimethylarginines: asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA). Toxins 9, 92 (2017).
  Google Scholar
• 18. Bode-Boger SM, Scalera F, Kielstein JT et al. Symmetrical dimethylarginine: a new combined parameter for renal function and extent of coronary artery disease. J. Am. Soc. Nephrol. 17, 1128–1134 (2006).
  MedlineGoogle Scholar
• 19. Kielstein JT, Salpeter SR, Bode-Boeger SM, Cooke JP, Fliser D. Symmetric dimethylarginine (SDMA) as endogenous marker of renal function-a meta-analysis. Nephrol. Dial. Transplant. 21, 2446–2451 (2006).
  Medline CASGoogle Scholar
• 20. Kasumov T, Edmison JM, Dasarathy S, Bennett C, Lopez R, Kalhan SC. Plasma levels of asymmetric dimethylarginines in patients with biopsy-proven nonalcoholic fatty liver disease. Met. Clin. Exp. 60, 776–781 (2011).
  CASGoogle Scholar
• 21. Wang L, Pal S, Sif S. Protein arginine methyltransferase 5 suppresses the transcription of the RB family of tumor suppressors in leukemia and lymphoma cells. Mol. Cell. Biol. 28(20), 6262–6277 (2008).
  Medline CASGoogle Scholar
• 22. Pal S, Baiocchi RA, Byrd JC, Grever MR, Jacob ST, Sif S. Low levels of miR-92b/96 induce PRMT5 translation and H3R8/H4R3 methylation in mantle cell lymphoma. EMBO J. 26(15), 3558–3569 (2007).
  Medline CASGoogle Scholar
• 23. Gerhart SV, Kellner WA, Thompson C et al. Activation of the p53-MDM4 regulatory axis defines the antitumour response to PRMT5 inhibition through its role in regulating cellular splicing. Sci. Rep. 8(9711), 1–15 (2018).
  Medline CASGoogle Scholar
• 24. Martens-Lobenhoffer J, Bode-Böger SM. Measurement of asymmetric dimethylarginine (ADMA) in human plasma: from liquid chromatography estimation to liquid chromatography-mass spectrometry quantification. Eur. J. Clin. Pharmacol. 62, 61–68 (2006). • Overview of current methods for quantification of ADMA and symmetric dimethyl arginine (SDMA).
  CASGoogle Scholar
• 25. Bishop MJ, Crow B, Norton D, Paliakov E, George J, Bralley JA. Direct analysis of un-derivatized asymmetric dimethylarginine (ADMA) and L-arginine from plasma using mixed-mode ion-exchange liquid chromatography-tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 859, 164–169 (2007). • ADMA methodology without derivatization and with selective daughter ion.
  Medline CASGoogle Scholar
• 26. Schwedhelm E, Tan-Andresen J, Maas R, Riederer U, Schulze F, Böger RH. Liquid chromatography-tandem mass spectrometry method for the analysis of asymmetric dimethylarginine in human plasma. Clin. Chem. 51(7), 1268–1271 (2005). • ADMA and SDMA methodology with derivatization and selective daughter ions.
  Medline CASGoogle Scholar
• 27. Schwedhelm E, Maas R, Tan-Andresen J, Schulze F, Riederer U, Böger RH. High-throughput liquid chromatographic-tandem mass spectrometric determination of arginine and demethylated arginine derivatives in human and mouse plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 851, 211–219 (2007).
  Medline CASGoogle Scholar
• 28. Martens-Lobenhoffer J, Bode-Böger SM. Chromatographic-mass spectrometric methods for the quantification of L-arginine and its methylated metabolites in biological fluids. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 851, 30–41 (2007). • Describes reported endogenous levels of ADMA and SDMA.
  Medline CASGoogle Scholar
• 29. Jones BR, Schultz GA, Eckstein JA, Ackermann BL. Surrogate matrix and surrogate analyte approaches for definitive quantitation of endogenous molecules. Bioanalysis 4(19), 2343–2356 (2012). • Describes parallelism experiments for the quantification of endogenous compounds using surrogate matrix approach.
  CASGoogle Scholar
• 30. Skelley AM, Mathies RA. Chiral separation of fluorescamine labelled amino acids using microfabricated capillary electrophoresis devices for extraterrestrial exploration. J. Chromatogr. A 1021, 191–199 (2003).
  Medline CASGoogle Scholar