The first fluorescent diboronic acid sensor specific for hepatocellular carcinoma cells expressing sialyl Lewis X

Chemistry and Biology

Volumn 11, Issue 4, 2004, Pages 439-448

  Yang, Wenqian ^a   Fan, Haiying ^b   Gao, Xingming ^a   Gao, Shouhai ^a   Karnati, Vishnu Vardhan Reddy ^a   Ni, Weijuan ^a   Hooks, W Borden ^b   Carson, John ^b   Weston, Brent ^b   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 ACETYLNEURAMINYL (2 3) GALACTOSYL (1 4) (FUCOPYRANOSYL (1 3)) N ACETYLGLUCOSAMINE; 5-ACETYLNEURAMINYL-(2-3)-GALACTOSYL-(1-4)-(FUCOPYRANOSYL-(1-3))-N-ACETYLGLUCOSAMINE; BORONIC ACID DERIVATIVE; DIAGNOSTIC AGENT; OLIGOSACCHARIDE;

ANIMAL; ARTICLE; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; GENE EXPRESSION REGULATION; GENETICS; HUMAN; IMMUNOLOGY; LIVER CELL CARCINOMA; LIVER TUMOR; METABOLISM; SYNTHESIS;

ANIMALS; BORONIC ACIDS; CARCINOMA, HEPATOCELLULAR; CELL LINE; FLUORESCENCE; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; LIVER NEOPLASMS; MOLECULAR STRUCTURE; OLIGOSACCHARIDES;

EID: 1942509587     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.03.021     Document Type: Article

References (44)

1. Fukuda M. Cell Surface Carbohydrates and Cell Development. 1992;CRC, Boca Raton.
2. Fukuda M. Cell surface carbohydrates. Cell-type specific expression Fukuda M., Hindsgaul O. Molecular Glycobiology. 1994;1-52 Oxford University, New York.
3. Fukuda M. Cell surface carbohydrates in hematopoietic cell differentiation and malignancy. Fukuda M. Cell Surface Carbohydrates and Cell Development. 1992;127-160 CRC, Boca Raton.
4. Dennis J.W. Changes in glycosylation associated with malignant transformation and tumor progression. Fukuda M. Cell Surface Carbohydrates and Cell Development. 1992;161-194 CRC, Boca Raton.
5. Jorgensen T., Berner A., Kaalhus O., Tveter K.J., Danielsen H.E., Bryne M. Up-regulation of the oligosaccharide sialyl Lewis X. A new prognostic parameter in metastatic prostate cancer Cancer Res. 55:1995;1817-1819.
6. Idikio H.A. Sialyl Lewis X, gleason grade and stage in nonmetastatic human prostate cancer. Glycoconj. J. 14:1997;875-877.
7. El-Serag H.B., Mason A.C. Rising incidence of hepatocellular carcinoma in the United States. N. Engl. J. Med. 340:1999;745-750.
8. Shacter E., Weitzman S.A. Chronic inflammation and cancer. Oncology. 16:2002;217-223.
9. Yago K., Zenita K., Ginya H., Sawada M., Ohmori K., Minoru O., Kannagi R., Lowe J. Expression of alpha(1,3)-fucosyltransferases which synthesize sialyl Le(x) and sialyl Le(a), the carbohydrate ligands for E- and P-selectins in human malignant cell lines. Cancer Res. 53:1993;5559-5565.
10. Goenner S., Cosson C., Boutron A., Legrand A., Moatti N. Interleukin-1 and interleukin-6 stimulate 2-methylaminoisobutyric acid uptake in HEPG2 cells. Int. J. Biochem. Cell Biol. 29:1997;667-674.
11. Mackiewicz A., Speroff T., Ganapathi M.K., Kushner I. Effects of cytokine combinations on acute phase protein production in two hepatoma cell lines. J. Immunol. 146:1991;3032-3037.
12. Minta J.O., Fung M., Paramasawara B. Transcriptional and post-transcriptional regulation of complement factor I (CFI) gene expression in HEPG2 cells by interleukin-6. Biochim. Biophys. Acta. 1442:1998;286-295.
13. Nakaya R., Kohgo Y., Mogi Y., Kakajima M., Kato J., Niitsu Y. Regulation of asialoglycoprotein receptor synthesis by inflammation-related cytokines in HEPG2 cells. J. Gastroenterol. 29:1994;24-30.
14. Brinkman-Van der Linden E.C.M., Mollicone R., Oriol R., Larson G., Van der Eijnden D.H., Van Dijk W. A missense mutation in the FUT6 gene results in total absense of alpha3-fucosylation of human alpha1-acid glycoprotein. J. Biol. Chem. 271:1996;14492-14495.
15. Mita Y., Aoyagi Y., Suda T., Asakura H. Plasma fucosyltransferase activity in patients with hepatocellular carcinoma, with special reference to correlation with fucosylated species of alpha-fetoprotein. J. Hepatol. 32:2000;946-954.
16. Fujiwara Y., Shimada M., Takenaka K., Kajiyama K., Shirabe K., Sugimachi K. The sialyl Lewis X expression in hepatocarcinogenesis. potential predictor for the emergence of hepatocellular carcinoma Hepatogastroenterology. 49:2002;213-217.
17. Nakakura E.K., Choti M.A. Management of hepatocellular carcinoma. Oncology. 14:2000;1085-1098.
18. Yang W., Gao S., Gao X., Karnati V., Ni W., Wang B., Hooks W.B., Carson J., Weston B. Diboronic acids as fluorescent probes for cells expressing sialyl Lewis X. Bioorg. Med. Chem. Lett. 12:2002;2175-2177.
19. Weston B.W., Hiller K.M., Mayben J.P., Manousos G.A., Bendt K.M., Liu R., Cusack J.C. Jr. Expression of human a(1,3)fucosyltransferase antisense sequences inhibits selectin-mediated adhesion and liver metastasis of colon carcinoma cells. Cancer Res. 59:1999;2127-2135.
20. Lorand J.P., Edwards J.O. Polyol complexes and structure of the benzeneboronate ion. J. Org. Chem. 24:1959;769-774.
21. Wang W., Gao X., Wang B. Boronic acid-based sensors for carbohydrates. Curr. Org. Chem. 6:2002;1285-1317.
22. Yang W., Gao X., Wang B. Boronic acid compounds as potential pharmaceutical agents. Med. Res. Rev. 23:2003;346-368.
23. James T.D., Sandanayake K.R.A.S., Iguchi R., Shinkai S. Novel saccharide-photoinduced electron transfer sensors based on the interaction of boronic acid and amine. J. Am. Chem. Soc. 117:1995;8982-8987.
24. James T.D., Sandanayake K.R.A.S., Shinkai S. Chiral discrimination of monosacchrides using a fluorescent molecular sensor. Nature. 374:1995;345-347.
25. Eggert H., Frederiksen J., Morin C., Norrild J.C. A new glucose-selective fluorescent bisboronic acid. First report of strong a-furanose complecation in aqueous solution at physiological pH. J. Org. Chem. 64:1999;3846-3852.
26. Adhikiri D.P., Heagy M.D. Fluorescent chemosensor for carbohydrates which shows large change in chelation-enhanced quenching. Tetrahedron Lett. 40:1999;7893-7896.
27. Wiskur S.L., Anslyn E.V. Using a synthetic receptor to create an optical-sensing ensemble for a class of analytes. A colorimetric assay for the aging of scotch J. Am. Chem. Soc. 123:2001;10109-10110.
28. Tong A.-J., Yamauchi A., Hayashita T., Zhang Z.-Y., Smith B.D., Teramae N. Boronic acid fluorophore/beta-cyclodextrin complex sensors for selective sugar recognition in water. Anal. Chem. 73:2001;1530-1536.
29. Yang W., He H., Drueckhammer D.G. Computer-guided design in molecular recognition. Design and synthesis of a glucopyranose receptor Angew. Chem. Int. Ed. Engl. 40:2001;1714-1718.
30. DiCesare N., Lakowicz J.R. New color chemosensors for monosaccharides based on azo dyes. Org. Lett. 3:2001;3891-3893.
31. Ward C.J., Patel P., James T.D. Molecular color sensors for monosaccharides. Org. Lett. 4:2002;477-479.
32. Springsteen G., Wang B. A detailed examination of boronic acid-diol complexation. Tetrahedron. 58:2002;5291-5300.
33. Wang W., Gao S., Wang B. Building fluorescent sensors by template polymerization. the preparation of a fluorescent sensor for D-fructose Org. Lett. 1:1999;1209-1212.
34. Gao S., Wang W., Wang B. Building fluorescent sensors for carbohydrates using template-directed polymerizations. Bioorg. Chem. 29:2001;308-320.
35. Sugasaki A., Sugiyasu K., Ikeda M., Takeuchi M., Shinkai S. First successful molecular design of an artificial Lewis oligosaccharide binding system utilizing positive homotropic allosterism. J. Am. Chem. Soc. 123:2001;10239-10244.
36. Wulff G. Selective binding to polymers via covalent bonds-The construction of chiral cavities as specific receptor-sites. Pure Appl. Chem. 54:1982;2093-2102.
37. Karnati V.R., Gao X., Gao S., Yang W., Ni W., Sankar S., Wang B. A glucose-selective fluorescence sensor based on boronic acid-diol recognition. Bioorg. Med. Chem. Lett. 12:2002;3373-3377.
38. Lin Y.-I., Lang S.A., Seifert C.M., Child R.G., Morton G.O., Fabio P.F. Aldehyde syntheses. Study of the preparation of. 9:1979;10. J. Org. Chem. 44, 4701-4703.anthracenedicarboaldehyde.
39. x, a hepatic necroinflammation-associated carbohydrate neoantigen, in human hepatocellular carcinomas. Cancer. 73:1994;1811-1816.
40. Jezequel-Cuer M., Dalix A.M., Flejou J.F., Durand G. Variations in human liver fucosyltransferase activities in hepatobiliary diseases. Liver. 12:1992;140-146.
41. Sasaki M., Kono N., Nakanuma Y. Neoexpression of Lewis Y antigen is a sensitive phenotypic change of the damaged intrahepatic bile ducts. Hepatology. 19:1994;138-144.
42. Hiller K.M., Mayben J.P., Bendt K.M., Manousos G.A., Singer K., Cameron H.S., Weston B.W. Transfection of alpha(1,3)fucosyltransferase antisense sequences impairs the proliferative and tumorigenic ability of human colon carcinoma cells. Mol. Carcinog. 27:2000;280-288.
43. Weston B.W., Nair R.P., Larsen R.D., Lowe J.B. Isolation of a novel human alpha(1,3)fucosyltransferase gene and molecular comparison to the human Lewis blood group alpha(1,3/1,4)fucosyltransferase. J. Biol. Chem. 267:1992;4152-4160.
44. Weston B.W., Smith P.L., Kelly R.J., Lowe J.B. Molecular cloning of a fourth member of a human alpha(1,3)fucosyltransferase gene family. J. Biol. Chem. 267:1992;24575-24584.