Abstract
Globotriaosylceramide (Gb3) is a cell membrane glycosphingolipid expressed by renal cells and gastrointestinal tract and overexpressed by many carcinomas. Subcellular distribution of this biomarker is highly significant for the development of drugs and therapy of diseases related to its interactions with cell surface. This paper describes a simple method for the synthesis of a deuterium-labeled fatty acyl side chain in its ceramide residue as a probe for those who are interested in NanoSIMS 50-based imaging technique in structural biology.
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REFERENCES
Naiki, M. and Marcus, D.M., Biochem. Biophys. Res. Commun., 1974, vol. 60, p. 1105. https://doi.org/10.1016/0006-291X(74)90426-4
Kihlberg, J., Hultgren, S.J., Normark, S., and Magnusson, G., J. Am. Chem. Soc., 1989, vol. 111, p. 6364. https://doi.org/10.1021/ja00198a056
Fukuda, M.N., Bothner, B., Lloyd, K.O., Retting, W.J., Tiller, P.R., and Dell, A., J. Biol. Chem., 1986, vol. 261, p. 5145. https://doi.org/10.1016/S0021-9258(19)89226-8
Kannagi, R., Levery, S.B., Ishigami, F., Hakomori, S., Shevinsky, L.H., Knowles, B.B., and Solter, D., J. Biol. Chem., 1983, vol. 258, p. 8934. https://doi.org/10.1016/S0021-9258(18)45178-2
Wiels, J., Holmes, E.H., Cochran, N., Tursz, T., and Hakomori, S., J. Biol. Chem., 1984, vol. 259, p. 14783. https://doi.org/10.1016/S0021-9258(17)42671-8
Kniep, B., Monner, D.A., Schwuléra, U., and Mühlradt, P.F., Eur. J. Biochem., 1985, vol. 149, p. 187. https://doi.org/10.1111/j.1432-1033.1985.tb08910.x
Bilodeau, M.T., Park, T.K., Hu, S., Randolf, J.T., Danishefsky, S.J., Livingston, P.O., and Zhang, S., J. Am, Chem. Soc., 1995, vol. 117, p. 7840. https://doi.org/10.1021/ja00134a043
Kint, J.A., Science, 1970, vol. 167, p. 1268. https://doi.org/10.1126/science.167.3922.1268
Jacob, F., Anugraham, M., Pochechueva, T., Tse, T.B.W.C., Alam, S., Guertler, R.; Bovin, N.V., Fedier, A., Hacker, N.F., Huflejt, M.E., Packer, N., and Heinzelmann-Schwarz, V.A., Br. J. Cancer, 2014, vol. 111, p. 1634. https://doi.org/10.1038/bjc.2014.455
Choi, S., Kim, J.A., Na, H.-Y., Cho, S.-E., Park, S., Jung, S.-C., and Suh, S.H., Arterioscler., Thromb., Vasc. Biol., 2014, vol. 34, p. 81. https://doi.org/10.1161/ATVBAHA.113.302200
Chen, L., Zhao, X-E., Lai, D., Song, Z., and Kong, F., Carbohydr. Res., 2006, vol. 341, p. 1174. https://doi.org/10.1016/j.carres.2006.03.029
Lingwood, C., Toxins, 2021, vol. 13, p. 378. https://doi.org/10.3390/toxins13060378
Kitov, P.I. and Bundle, D.R., J. Chem. Soc., Perkin Trans. 1, 2001, p. 838. https://doi.org/10.1039/B009685G
Behnam-Motlagh, P., Tyler, A., Grankvist, K., and Johansson, A., Toxins, 2010, vol. 2, no. 10, p. 2467. https://doi.org/10.3390/toxins2102467
Uzawa, H., Ito, H.; Izumi, M., Tokuhisa, H., Taguchi, K., and Minoura, N., Tetrahedron, 2005, vol. 61, p. 5895. https://doi.org/10.1016/j.tet.2005.03.102
Gargano, J.M., Ngo, T., Kim, J.Y., Acheson, D.W.K., and Lees, W.J., J. Am. Chem. Soc., 2001, vol. 123, p. 12909. https://doi.org/10.1021/ja016305a
Hansen, H.C. and Magnusson, G., Carbohydr. Res., 1998, vol. 307, p. 233. https://doi.org/10.1016/S0008-6215(98)00020-2
Weiss, A., Bacterial Toxins: Genetics, Cellular Biology and Practical Applications, Proft, T., Ed., 2013, Norfolk (UK): Caister Academic, 2013. https://doi.org/10.1002/cbic.201300696
Müller, D., Vic, G., Critchley, P., Crout, D.H.G., Lea, N., Roberts, L., and Lord, J. M., J. Chem. Soc., Perkin Trans. 1, 1998, p. 2287. https://doi.org/10.1039/A801429I
Aly, M.R.E, Rochaix, P., Amessou, M., Johannes, L., and Florent, J.-C., Carbohydr. Res., 2006, vol. 341, no. 12, p. 2026. https://doi.org/10.1016/j.carres.2006.03.044
El Alaoui, A., Schmidt, F., Amessou, M., Sarr, M., Decaudin, D., Florent, J.-C., and Johannes, L., Angew. Chem., Int. Ed., 2007, vol. 46, p. 6469. https://doi.org/10.1002/anie.200701270
Johannes, L. and Romer, W., Nat. Rev. Microbiol., 2010, vol. 8, p. 105. https://doi.org/10.1038/nrmicro2279
Maak, M., Nitsche, U., Keller, L., Wolf, P., Sarr, M., Thiebaud, M., Rosenberg, R., Langer, R., Kleeff, J., Friess, H., Johannes, L., and Janssen, K.-P., Mol. Cancer Ther., 2011, vol. 10, no. 10, p. 1918. https://doi.org/10.1158/1535-7163.MCT-11-0006
Römer, W., Berland, L., Chambon, V., Gaus, K., Windschiegl, B., Tenza, D., Aly, M.R.E., Fraisier, V., Florent, J.-C., Perrais, D., Lamaze, C., Raposo, G., Steinem, C., Sens, P.; Bassereau, P., and Johannes, L., Nature, 2007, vol. 450, p. 670. https://doi.org/10.1038/nature05996
Pezeshkian, W., Chaban, V.V., Johannes, L., Shillcock, J., Ipsen, J.H., and Khandelia, H., Soft Matter, 2015, vol. 11, p. 1352. https://doi.org/10.1039/C4SM02456G
Boxer, S.G., Kraft, M.L., and Weber, P.K., Annu. Rev. Biophys., 2009, vol. 38, p. 53. https://doi.org/10.1146/annurev.biophys.050708.133634
Kraft, M.L., Fishel, S.F., Marxer, C.G., Weber, P.K., Hutcheon, I.D., and Boxer, S.G., Appl. Surf. Sci., 2006, vol. 252, p. 6950. https://doi.org/10.1016/j.apsusc.2006.02.116
Rӧmer, W., Wu, T.-D., Duchambon, P., Amessou, M., Carrez, D., Johannes, L., and Guerquin-Kern, J.-L., Appl. Surf. Sci., 2006, vol. 252, p. 6925. https://doi.org/10.1016/j.apsusc.2006.02.183
Zhang, J., Kitova, E.N., Li, J., Eugenio, L., Ng, K., and Klassen, J.S., J. Am. Soc. Mass Spectrom., 2016, vol. 27, p. 83. https://doi.org/10.1007/s13361-015-1263-2
Sibold, J., Ahadi, S., Werz, D.B., and Steinem, C., Eur. Biophys. J., 2021, vol. 50, p. 109. https://doi.org/10.1007/s00249-020-01461-w
Sibold, J., Kettelhoit, K., Vuong, L., Liu, F., Werz, D.B., and Steinem, C., Angew. Chem., Int. Ed., 2019, vol. 58, no. 49, p. 17805. https://doi.org/10.1002/anie.201910148
Zelnik, D.I., Volpert, G., Viiri, L.E., Kauhanen, D., Arazi, T., Aalto-Setälä, K., Laaksonen, R., and Futeran, A.H., J. Lipid Res., 2020, vol. 61, no. 10, p. 1341. https://doi.org/10.1194/jlr.RA120000984
ACKNOWLEDGMENTS
The authors are grateful to the Deanship of Scientific Research at the Taif University (Taif, Saudi Arabia) for funding and support according to project no. TURSP2020/27 and to the Curie Institute (Paris, France) for supporting and facilitating performing this study.
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Aly, M.R.E., Azab, I.H.E. Synthesis of a Deuterium-Labeled Globotriaosylceramide Probe for Potential Imaging of Subcellular Localization of Gb3 Using NanoSIMS. Russ J Org Chem 57, 1719–1724 (2021). https://doi.org/10.1134/S1070428021100213
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DOI: https://doi.org/10.1134/S1070428021100213