Synthesis of bifunctional lipophilic constructs

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Abstract

An ability of glycolipids to embed membrane of living cells opens an opportunity to modify cellular surface via insertion of synthetic lipophilic constructs carrying given glycan (or any other molecular fragment). Detection of thus inserted glycans by fluorescent microscopy requires treatment with corresponding fluorescently labeled antibodies. Di- (IgG) and decavalent (IgM) antibodies can significantly affect the distribution of glycolipids in the membrane, therefore direct visualization of embedded lipophilic constructs is required. To achieve this, fluorescent tag must be included in the composition of the lipophilic constructs and at the same time be located at a sufficient distance from glycan part. Here we propose two approaches to the synthesis of these compounds and describe obtaining of two constructs carrying A (type 2) tetrasaccharide and either fluorescein or sulfo-cyanine-3.

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About the authors

D. O. Anisimova

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

Email: imryzhov@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

M. S. Savchenko

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

Email: imryzhov@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. B. Tuzikov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

Email: imryzhov@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. S. Paramonov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

Email: imryzhov@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. O. Chizhov

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Email: imryzhov@gmail.com
Russian Federation, Leninskiy prosp. 47, Moscow, 119991

N. V. Bovin

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

Email: imryzhov@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

I. M. Ryzhov

Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry of the Russian Academy of Sciences

Author for correspondence.
Email: imryzhov@gmail.com
Russian Federation, ul. Miklukho-Maklaya 16/10, Moscow, 117997

References

  1. Rapoport E.M., Khasbiullina N.R., Komarova V.A., Ryzhov I.M., Gorbatch M.M., Tuzikov A.B., Khaidukov S.V., Popova I.S., Korchagina E.Y, Henry S.M., Bovin N.V. // Biochim. Biophys. Acta Biomembr. 2021. V. 1863. P. 183645. https://doi.org/10.1016/j.bbamem.2021.183645
  2. Frame T., Carroll T., Korchagina E., Bovin N., Henry S. // Transfusion. 2007. V. 47. P. 876–882. https://doi.org/10.1111/j.1537-2995.2007.01204.x
  3. Korchagina E., Tuzikov A., Formanovsky A., Popova I., Henry S., Bovin N. // Carbohydr. Res. 2012. V. 356. P. 238–246. https://doi.org/10.1016/j.carres.2012.03.044
  4. Henry S., Williams E., Barr K., Korchagina E., Tuzikov A., Ilyushina N., Abayzeed S.A, Webb K.F., Bovin N. // Sci. Rep. 2018. V. 8. P. 2845. https://doi.org/10.1038/s41598-018-21186-3
  5. Zalygin A., Solovyeva D., Vaskan I., Henry S., Schaefer M., Volynsky P., Tuzikov A., Korchagina E., Ryzhov I., Nizovtsev A., Mochalov K., Efremov R., Shtykova E., Oleinikov V., Bovin N. // ChemistryOpen. 2020. V. 9. P. 641–648. https://doi.org/10.1002/open.201900276
  6. Ryzhov I.M., Tuzikov A.B., Nizovtsev A.V., Baidakova L.K., Galanina O.E., Shilova N.V., Ziganshina M.M., Dolgushina N.V., Bayramova G.R., Sukhikh G.T., Williams E.C., Nagappan R., Henry S.M., Bovin N.V. // Bioconjug. Chem. 2021. V. 32. P. 1606– 1616. https://doi.org/10.1021/acs.bioconjchem.1c00186
  7. Lan C.-C., Blake D., Henry S., Love D.R. // J. Fluoresc. 2012. V. 22. P. 1055–1063. https://doi.org/10.1007/s10895-012-1043-3
  8. Barr K., Korchagina E., Ryzhov I., Bovin N., Henry S. // Transfusion. 2014. V. 54. P. 2477–2484. https://doi.org/10.1111/trf.12661
  9. Williams E., Korchagina E., Frame T., Ryzhov I., Bovin N., Henry S. // Transfusion. 2016. V. 56. P. 325– 333. https://doi.org/10.1111/trf.13384
  10. Rapoport E.M., Ryzhov I.M., Slivka E.V., Korchagina E.Y., Popova I.S., Khaidukov S.V., André S., Kaltner H., Gabius H.J., Henry S., Bovin N.V. // Biomolecules. 2023. V. 13. P. 1–12. https://doi.org/10.3390/biom13081166
  11. Mikhalyov I.I., Molotkovsky Jul.G. // Russ. J. Bioorg. Chem. 2003. V. 29. P. 168–174. https://doi.org/10.1023/A:1023264516818
  12. Yamaguchi E., Komura N., Tanaka H.N., Imamura A., Ishida H., Groux-Degroote S., Mühlenhoff M., Suzuki K.G.N., Ando H. // Glycoconj. J. 2023. V. 40. P. 247–257. https://doi.org/10.1007/s10719-023-10102-1
  13. Ryzhov I.M., Korchagina E.Y., Popova I.S., Tyrtysh T.V., Paramonov A.S., Bovin N.V. // Carbohydr. Res. 2016. V. 430. P. 59–71. https://doi.org/10.1016/j.carres.2016.04.029
  14. Petrakova D.O., Savchenko M.S., Popova I.S., Tuzikov A.B., Paramonov A.S., Chizhov A.O., Bovin N.V., Ryzhov I.M. // Russ. J. Bioorg. Chem. 2023. V. 49. P. 785–796. https://doi.org/10.1134/S1068162023040143
  15. Vokhmyanina O.A., Rapoport E.M., André S., Severov V.V., Ryzhov I., Pazynina G.V., Korchagina E., Gabius H.-J., Bovin N.V. // Glycobiology. 2012. V. 22. P. 1207–1217. https://doi.org/10.1093/glycob/cws079
  16. Henry S.M., Bovin N.V. // J. R. Soc. New Zeal. 2019. V. 49. P. 100–113. https://doi.org/10.1080/03036758.2018.1546195
  17. Twibanire J.D.A.K., Grindley T.B. // Org. Lett. 2011. V. 13. P. 2988–2991. https://doi.org/10.1021/ol201005s
  18. Ryzhov I.M., Tuzikov A.B., Perry H., Korchagina E.Y., Bovin N.V. // ChemBioChem. 2019. V. 20. P. 131–133. https://doi.org/10.1002/cbic.201800289
  19. Meldal M., Tornøe C.W. // Chem. Rev. 2008. P. 108. P. 2952–3015. https://doi.org/10.1021/cr0783479
  20. Baskin J.M., Prescher J.A., Laughlin S.T., Agard N.J., Chang P.V., Miller I.A., Lo A., Codelli J.A., Bertozzi C.R. // Proc. Natl. Acad. Sci. USA. 2007. V. 104. P. 16793–16797. https://doi.org/10.1073/pnas.0707090104
  21. Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B. // Angew. Chemie Int. Ed. Engl. 2002. V. 41. P. 2596– 2599. https://doi.org/10.1002/1521-3773(20020715)41: 14<2596::AID-ANIE2596>3.0.CO,2-4
  22. Hong V., Presolski S.I., Ma C., Finn M.G. // Angew. Chemie Int. Ed. Engl. 2009. V. 48. P. 9879–9883. https://doi.org/10.1002/anie.200905087
  23. Chan T.R., Hilgraf R., Sharpless K.B., Fokin V.V. // Org. Lett. 2004. V. 6. P. 2853–2855. https://doi.org/10.1021/ol0493094
  24. Sturabotti E., Vetica F., Toscano G., Calcaterra A., Martinelli A., Migneco L.M., Leonelli F. // Molecules. 2023. V. 28. P. 581. https://doi.org/10.3390/molecules28020581
  25. Tyrtysh T.V., Korchagina E.Y., Ryzhov I.M., Bovin N.V. // Carbohydr. Res. 2017. V. 449. P. 65–84. https://doi.org/10.1016/j.carres.2017.06.014
  26. Meloncelli P.J., Lowary T.L. // Carbohydr. Res. 2010. V. 345. P. 2305–2322. https://doi.org/10.1016/j.carres.2010.08.012

Supplementary files

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2. Fig. 1. Common structural fragments of the obtained SLKs: tetrasaccharide A (type 2) and the CMG–DOPE block.

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3. Scheme 1. Preparation of SLC (9). Reagents and conditions: i – TBTU, DIPEA/DMF, 75%; ii – 95% CF3COOH, 4°C, 5 min, quantitative yield; iii – Ad(ONSu)2 (10 equiv.), DMSO, iv – NaHCO3 (aq.) (50 mM)–i-PrOH (2 : 1), 87% (in two stages); v – CuSO4, NaAsc, THPTA/DMSO–water (1 : 1), 77%.

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4. Scheme 2. Racemization upon conjugation with tetrasaccharide (1). Reagents and conditions: i – DIPEA/DMSO, 85%; ii – TBTU, DIPEA/DMF, then compound (1), 72%, L/D = 1 : 1.

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5. Scheme 3. Preparation of SLC (18). Reagents and conditions: i – Boc2O, Et3N/MeOH, 81%; ii – TBTU, DIPEA/DMF, then compound (1); iii – 95% CF3COOH, 4°C, 5 min, 72% (in two stages); iv – DIPEA/DMSO, 89%; v – CuSO4, NaAsc, THPTA/DMSO–water (1:1), 86%.

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