LC-MS/MS glycomic analyses of free and conjugated forms of the sialic acids, Neu5Ac, Neu5Gc and KDN in human throat cancers

Glycobiology

Volumn 25, Issue 12, 2015, Pages 1362-1374

  Wang, Fang ^a   Xie, Baoying ^a   Wang, Bing ^a,b   Troy, Frederic A ^a,c  

^a XIAMEN UNIVERSITY   (China)

^b CHARLES STURT UNIVERSITY   (Australia)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Biomarker; Mass spectrometry; Sialic acids; Throat cancer

Indexed keywords

2 KETO 3 DEOXY DEXTRO GLYCERO DEXTRO GALACTO NONONIC ACID; BIOLOGICAL MARKER; N ACETYLNEURAMINIC ACID; N GLYCOLYNEURAMINIC ACID; SIALIC ACID; UNCLASSIFIED DRUG; 3-DEOXYGLYCERO-GALACTO-NONULOSONIC ACID; SIALIC ACID DERIVATIVE; SUGAR ACID; TUMOR MARKER;

ADULT; ARTICLE; CANCER PROGNOSIS; CANCER STAGING; CONJUGATION; DIAGNOSTIC VALUE; EARLY CANCER; FEMALE; GLYCOBIOLOGY; HUMAN; HUMAN TISSUE; LIQUID CHROMATOGRAPHY; LYMPH NODE METASTASIS; MAJOR CLINICAL STUDY; MALE; MIDDLE AGED; PHARYNX CANCER; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; TUMOR BIOPSY; TUMOR DIFFERENTIATION; HEAD AND NECK TUMOR; METABOLISM; PATHOLOGY;

BIOMARKERS, TUMOR; HEAD AND NECK NEOPLASMS; HUMANS; LYMPHATIC METASTASIS; SIALIC ACIDS; SUGAR ACIDS;

EID: 84959349779     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwv051     Document Type: Article

References (39)

1. Angata T, Kitazume S, Terada T, Kitajima K, Inoue S, Troy FA II, Inoue Y. 1994. Identification, characterization, and developmental expression of a novel alpha 2->8-KDN-transferase which terminates elongation of alpha 2->8-linked oligo-polysialic acid chain synthesis in trout egg polysialoglycoproteins. Glycoconj J. 11(5):493-499.
2. Angata T, Nakata D, Matsuda T, Kitajima K. 1999. Elevated expression of free deaminoneuraminic acid in mammalian cells cultured in mannose-rich media. Biochem Biophys Res Commun. 261(2):326-331.
3. Angata T, Nakata D, Matsuda T, Kitajima K, Troy FA II. 1999. Biosynthesis of KDN (2-keto-3-deoxy-D-glycero-D-galacto-nononic acid). Identification and characterization of a KDN-9-phosphate synthetase activity from trout testis. J Biol Chem. 274(33):22949-22956.
4. Angata T, Varki A. 2002. Chemical diversity in the sialic acids and related alpha-keto acids: An evolutionary perspective. Chem Rev. 102(2):439-469.
5. Campanero-Rhodes MA, Solis D, Carrera E, de la Cruz MJ, Diaz-Maurino T. 1999. Rat liver contains age-regulated cytosolic 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid (Kdn). Glycobiology. 9(6):527-532.
6. Chen Y, Pan L, Liu N, Troy FA, Wang B. 2014. LC-MS/MS quantification of N-acetylneuraminic acid, N-glycolylneuraminic acid and ketodeoxynonulosonic acid levels in the urine and potential relationship with dietary sialic acid intake and disease in 3- to 5-year-old children. Br J Nutr. 111(2):332-341.
7. Chen X, Varki A. 2010. Advances in the biology and chemistry of sialic acids. ACS Chem Biol. 5(2):163-176.
8. Colley KJ, Kitajima K, Sato C. 2014. Polysialic acid: Biosynthesis, novel functions and applications. Crit Rev Biochem Mol Biol. 49(6):498-532.
9. Davis JA, Wu XH, Wang L, DeRossi C, Westphal V, Wu R, Alton G, Srikrishna G, Freeze HH. 2002. Molecular cloning, gene organization, and expression of mouse MPI encoding phosphomannose isomerase. Glycobiology. 12(7):435-442.
10. Diaz SL, Padler-Karavani V, Ghaderi D, Hurtado-Ziola N, Yu H, Chen X, Brinkman-Van der Linden EC, Varki A, Varki NM. 2009. Sensitive and specific detection of the non-human sialic acid N-glycolylneuraminic acid in human tissues and biotherapeutic products. PLoS ONE. 4(1):e4241.
11. Drake PM, Nathan JK, Stock CM, Chang PV, Muench MO, Nakata D, Reader JR, Gip P, Golden KP, Weinhold B, et al. 2008. Polysialic acid, a glycan with highly restricted expression, is found on human and murine leukocytes and modulates immune responses. J Immunol. 181(10):6850-6858.
12. Go S, Sato C, Furuhata K, Kitajima K. 2006. Oral ingestion of mannose alters the expression level of deaminoneuraminic acid (KDN) in mouse organs. Glycoconj J. 23(5-6):411-421.
13. Go S, Sato C, Yin J, Kannagi R, Kitajima K. 2007. Hypoxia-enhanced expression of free deaminoneuraminic acid in human cancer cells. Biochem Biophys Res Commun. 357(2):537-542.
14. Inoue S, Kitajima K. 2006. KDN (deaminated neuraminic acid): Dreamful past and exciting future of the newest member of the sialic acid family. Glycoconj J. 23(5-6):277-290.
15. Inoue S, Kitajima K, Inoue Y. 1996. Identification of 2-keto-3-deoxy-D-glycero - galactonononic acid (KDN, deaminoneuraminic acid) residues in mammalian tissues and human lung carcinoma cells. Chemical evidence of the occurrence of KDN glycoconjugates in mammals. J Biol Chem. 271(40):24341-24344.
16. Inoue S, Lin SL, Chang T, Wu SH, Yao CW, Chu TY, Troy FA II, Inoue Y. 1998. Identification of free deaminated sialic acid (2-keto-3-deoxy-D-glycero-D-galacto-nononic acid) in human red blood cells and its elevated expression in fetal cord red blood cells and ovarian cancer cells. J Biol Chem. 273(42):27199-27204.
17. Inoue S, Poongodi GL, Suresh N, Chang T, Inoue Y. 2006. Identification and partial characterization of soluble and membrane-bound KDN(deaminoneuraminic acid)-glycoproteins in human ovarian teratocarcinoma PA-1, and enhanced expression of free and bound KDN in cells cultured in mannose-rich media. Glycoconj J. 23(5-6):401-410.
18. Iwasaki M, Inoue S, Troy FA. 1990. A new sialic acid analogue, 9-O-acetyldeaminated neuraminic acid, and alpha -2,8-linked O-acetylated poly(N-glycolylneuraminyl) chains in a novel polysialoglycoprotein from salmon eggs. J Biol Chem. 265(5):2596-2602.
19. Kanato Y, Kitajima K, Sato C. 2008. Direct binding of polysialic acid to a brain-derived neurotrophic factor depends on the degree of polymerization. Glycobiology. 18(12):1044-1053.
20. Kimura M, Hama Y, Sumi T, Asakawa M, Rao BN, Horne AP, Li SC, Li YT, Nakagawa H. 1994. Characterization of a deaminated neuraminic acid-containing glycoprotein from the skin mucus of the loach, Misgurnus anguillicaudatus. J Biol Chem. 269(51):32138-32143.
21. Knirel YA, Kocharova NA, Shashkov AS, Kochetkov NK, Mamontova VA, Soloveva TF. 1989. Structure of the capsular polysaccharide of Klebsiella ozaenae serotype K4 containing 3-deoxy-D-glycero-D-galacto-nonulosonic acid. Carbohydr Res. 188:145-155.
22. Malykh YN, Schauer R, Shaw L. 2001. N-Glycolylneuraminic acid in human tumours. Biochimie. 83(7):623-634.
23. Nadano D, Iwasaki M, Endo S, Kitajima K, Inoue S, Inoue Y. 1986. A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). Its unique occurrence at the nonreducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trout eggs. J Biol Chem. 261(25):11550-11557.
24. Nakata D, Munster AK, Gerardy-Schahn R, Aoki N, Matsuda T, Kitajima K. 2001. Molecular cloning of a unique CMP-sialic acid synthetase that effectively utilizes both deaminoneuraminic acid (KDN) and N-acetylneuraminic acid (Neu5Ac) as substrates. Glycobiology. 11(8):685-692.
25. Nakata D, Troy FA 2nd. 2005. Degree of polymerization (DP) of polysialic acid (polySia) on neural cell adhesion molecules (N-CAMS): Development and application of a new strategy to accurately determine the DP of polySia chains on N-CAMS. J Biol Chem. 280(46):38305-38316.
26. Samraj AN, Laubli H, Varki N, Varki A. 2014. Involvement of a non-human sialic acid in human cancer. Front Oncol. 4:33.
27. Samraj AN, Pearce OM, Laubli H, Crittenden AN, Bergfeld AK, Banda K, Gregg CJ, Bingman AE, Secrest P, Diaz SL, et al. 2015. A red meat-derived glycan promotes inflammation and cancer progression. Proc Natl Acad Sci USA. 112(2):542-547.
28. Sato C, Fukuoka H, Ohta K, Matsuda T, Koshino R, Kobayashi K, Troy FA II, Kitajima K. 2000. Frequent occurrence of pre-existing alpha 2->8-linked disialic and oligosialic acids with chain lengths up to 7 Sia residues in mammalian brain glycoproteins. Prevalence revealed by highly sensitive chemical methods and anti-di-, oligo-, and poly-Sia antibodies specific for defined chain lengths. J Biol Chem. 275(20):15422-15431.
29. Sato C, Kitajima K. 2013. Disialic, oligosialic and polysialic acids: Distribution, functions and related disease. J Biochem. 154(2):115-136.
30. Schauer R. 2009. Sialic acids as regulators of molecular and cellular interactions. Curr Opin Struct Biol. 19(5):507-514.
31. Schnaar RL, Gerardy-Schahn R, Hildebrandt H. 2014. Sialic acids in the brain: Gangliosides and polysialic acid in nervous system development, stability, disease, and regeneration. Physiol Rev. 94(2):461-518.
32. Song Y, Kitajima K, Inoue S, Inoue Y. 1991. Isolation and structural elucidation of a novel type of ganglioside, deaminated neuraminic acid (KDN)-containing glycosphingolipid, from rainbow trout sperm. The first example of the natural occurrence of KDN-ganglioside, (KDN)GM3. J Biol Chem. 266(32):21929-21935.
33. Spiessl B, Scheibe O, Wagner G. 1982. UICC TNM-ATLAS: Guide to the Classification of Malignant Tumors. Berlin: Springer-Verlag.
34. Terada T, Kitazume S, Kitajima K, Inoue S, Ito F, Troy FA, Inoue Y. 1993. Synthesis of CMP-deaminoneuraminic acid (CMP-KDN) using the CTP: CMP-3-deoxynonulosonate cytidylyltransferase from rainbow trout testis. Identification and characterization of a CMP-KDN synthetase. J Biol Chem. 268(4):2640-2648.
35. Troy FA 2nd. 1992. Polysialylation: From bacteria to brains. Glycobiology. 2(1):5-23.
36. Troy FA. 1995. Sialobiology and polysialic acid glycotope: Occurrence, structure, function, synthesis, and glycopathology. In: Rosenberg A, editor. Biology of the Sialic Acids. New York: Plenum Press. p. 95-144.
37. Valianpour F, Abeling NG, Duran M, Huijmans JG, Kulik W. 2004. Quantification of free sialic acid in urine by HPLC-electrospray tandem mass spectrometry: A tool for the diagnosis of sialic acid storage disease. Clin Chem. 50(2):403-409.
38. van der Ham M, Prinsen BH, Huijmans JG, Abeling NG, Dorland B, Berger R, de Koning TJ, de Sain-van der Velden MG. 2007. Quantification of free and total sialic acid excretion by LC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 848(2):251-257.
39. Zanetta JP, Pons A, Iwersen M, Mariller C, Leroy Y, Timmerman P, Schauer R. 2001. Diversity of sialic acids revealed using gas chromatography/mass spectrometry of heptafluorobutyrate derivatives. Glycobiology. 11(8):663-676.