Synthesis of bifunctional lipophilic constructs

封面

如何引用文章

全文:

开放存取 开放存取
受限制的访问 ##reader.subscriptionAccessGranted##
受限制的访问 订阅存取

详细

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.

全文:

受限制的访问

作者简介

D. Anisimova

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

Email: imryzhov@gmail.com
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997

M. Savchenko

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

Email: imryzhov@gmail.com
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Tuzikov

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

Email: imryzhov@gmail.com
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Paramonov

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

Email: imryzhov@gmail.com
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997

A. Chizhov

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

Email: imryzhov@gmail.com
俄罗斯联邦, Leninskiy prosp. 47, Moscow, 119991

N. Bovin

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

Email: imryzhov@gmail.com
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997

I. Ryzhov

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

编辑信件的主要联系方式.
Email: imryzhov@gmail.com
俄罗斯联邦, ul. Miklukho-Maklaya 16/10, Moscow, 117997

参考

  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

补充文件

附件文件
动作
1. JATS XML
下载
2. Fig. 1. Common structural fragments of the obtained SLKs: tetrasaccharide A (type 2) and the CMG–DOPE block.

下载 (81KB)
索引源数据
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%.

下载 (92KB)
索引源数据
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.

下载 (95KB)
索引源数据
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%.

下载 (86KB)
索引源数据

版权所有 © Russian Academy of Sciences, 2024

##common.cookie##