SULFATED DERIVATIVES OF ARABINOGALACTAN AND THEIR ANTICOAGULANT ACTIVITY

UDC 547.458+615.273.53

  • Svetlana Alekseyevna Kuznetsova Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS” http://orcid.org/0000-0002-6617-1641 Email: kuznetssvetl@rambler.ru
  • Natal'ya Yur'yevna Vasilyeva Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”; Siberian Federal University Email: vasilyeva.nata@mail.ru
  • Natal'ya Nikolayevna Drozd FGBU "National Medical Research Center of Hematology" of the Ministry of Health of the Russian Federation https://orcid.org/0000-0002-9278-7757 Email: nndrozd@mail.ru
  • Mikhail Aleksandrovich Mikhailenko Institute of Solid State Chemistry and Mechanochemistry SB RAS http://orcid.org/0000-0002-1233-5225 Email: mikhailenko@solid.nsc.ru
  • Tat'yana Petrovna Shakhtshneider Institute of Solid State Chemistry and Mechanochemistry SB RAS; Novosibirsk State University http://orcid.org/0000-0001-8464-2921 Email: shah@solid.nsc.ru
  • Yuriy Nikolayevich Malyar Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”; Siberian Federal University http://orcid.org/0000-0001-9380-0290 Email: yumalyar@gmail.com
  • Boris Nikolayevich Kuznetsov Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”; Siberian Federal University https://orcid.org/0000-0001-6309-6482 Email: inm@icct.ru
  • Nikolay Vasil'yevich Chesnokov Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS” https://orcid.org/0000-0001-8953-4321 Email: cnv@icct.ru
Keywords: sulfated arabinogalactan, sulfur content, molecular weight, anticoagulant activity

Abstract

The IR spectra and molecular mass distribution of arabinogalactan sulfates in the form of sodium and ammonium salts, obtained using various sulfating reagents, were compared.

According to the obtained data, the sulfated derivatives of arabinogalactan differ from each other by the nature of the hydrogen bonds and the molecular weight distribution.

Using coagulological tests at the activation of coagulation of platelet-poor human plasma, in vitro study of the anticoagulant properties of arabinogalactan sulfated derivatives in various salt forms differing in methods of  preparation, degree of sulfation and molecular weight was conducted.

It was established that the sample in the form of arabinogalactan sodium salt (SAG 1) with a sulfur content of 13.2 wt.% аnd a polydispersity degree of 1.52 showed 2 times more anticoagulant activity than the sample in the form of ammonium salt of arabinogalactan (SAG 2) with the sulfur content of 6.6 wt.% and the degree of polydispersity of 1.30.

Antithrombin (aIIa) activity of samples obtained by sulfation with pyridine and sulfuric anhydride complex (SAG 1) and sulfamic acid complex (SAG 2) was, respectively, 23.42±1.86 and 10.20±1.50 U/mg; the anti-factor Xa activity of SAG 1 and SAG 2 was 2.13±0.42 and 0.37±0.08 U/mg; and the ratio aIIa/aXa for SAG1 and SAG 2 was 11 and 28, respectively.

The less activity of antifactor Xa(aXA) of SAG as compared to unfractionated heparin (UFG) and higher rations of activities aIIa/aXa may contribute the less provocation of bleeding by SAG samples in the comparition with UFG.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Author Biographies

Svetlana Alekseyevna Kuznetsova, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”

доктор химических наук, профессор, главный научный сотрудник

Natal'ya Yur'yevna Vasilyeva, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”; Siberian Federal University

кандидат химических наук, доцент, старший научный сотрудник

Natal'ya Nikolayevna Drozd, FGBU "National Medical Research Center of Hematology" of the Ministry of Health of the Russian Federation

доктор биологических наук, ведущий научный сотрудник

Mikhail Aleksandrovich Mikhailenko, Institute of Solid State Chemistry and Mechanochemistry SB RAS

кандидат химических наук, научный сотрудник

Tat'yana Petrovna Shakhtshneider, Institute of Solid State Chemistry and Mechanochemistry SB RAS; Novosibirsk State University

доктор химических наук, ученый секретарь

Yuriy Nikolayevich Malyar, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”; Siberian Federal University

кандидат химических наук, научный сотрудник

Boris Nikolayevich Kuznetsov, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”; Siberian Federal University

доктор химических наук, профессор, заместитель директора по научной работе, заведующий лабораторией, заведующий кафедрой

Nikolay Vasil'yevich Chesnokov, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”

доктор химических наук,  директор ИХХТ СО РАН

References

Zamani M., Khafaji M., Naji M., Vossoughi M., Alemzadeh I., Haghighipour N. A Scientific Reports, 2017, vol. 7, no. 1, article 4455, DOI: 10.1038/s41598-017-04510-1.

Krylov V.B., Ustyuzhanina N.Ye., Nifant'yev N.E. Bioorganicheskaya khimiya, 2011, vol. 37, no. 6, pp. 745–779. (in Russ.).

Mourão P.A. Marine Drugs, 2015, vol. 13, no. 5, pp. 2770–2784, DOI: 10.3390/md13052770.

Durić K., Kovac Besovic E.E., Njksic H., Muratovic S., Sofic E. Bosnian Journal of Basic Medical Sciences, 2015, vol. 15, no. 2, pp. 9–14, DOI: 10.17305/bjbms.2015.384.

Jiao G., Yu G., Zhang J., Ewart S. Marine Drugs, 2011, vol. 9, no. 2, pp. 196–223, DOI: 10.3390/md9020196.

Alban S., Schauerte A., Franz G. Carbohydrate Polymers, 2002, vol. 47, no. 3, pp. 267–276, DOI: 10.1016/S0144-8617(01)00178-3.

Desai U.R. Medical Research Reviews, 2004, vol. 24, no. 2, pp. 151–181, DOI: 10.1002/med.10058.

Patent 2571555 (RU). 20.12.2015. (in Russ.).

Huang H., Zhang W.-D. Journal of Fiber Bioengineering and Informatics, 2010, vol. 3, no. 1, pp. 32–39, DOI: 10.3993/jfbi06201006.

Paulsen B.S., Barsett H. Polysaccharides 1: Structure, characterization and use. Berlin: Springer-Verlag, 2005, pp. 69–101, DOI: 10.1007/b136817.

Oliveira R.C.R, Almeida R.R., Gonçalves T.A. Journal of Developing Drugs, 2016, vol. 5, no. 3. Pp 1–3, DOI: 10.4172/2329-6631.1000166.

Ciancia M., Quintana I., Vizcargüénaga M. I., Kasulin L., de Dios A., Estevez J. M., Cerezo A.S. International Journal of Biological Macromolecules, 2007, vol. 41, no. 5, pp. 641–649, DOI: 10.1016/j.ijbiomac.2007.08.007.

de Raucourt E., Mauray S., Chaubet F., Maiga-Revel O., Jozefowicz M., Fischer A. M. Journal of Biomedical Mate-rials Research, 1998, vol. 41, no. 1, pp. 49–57, DOI: 10.1002/(SICI)1097-4636(199807)41:1<49::AID-JBM6>3.0.CO;2-Q.

Pereira M.S., Melo F.R., Mourão P.A.S. Glycobiology, 2002, vol. 12, no. 10, pp. 573–580, DOI: 10.1093/glycob/cwf077.

Chaidedgumjorn A., Toyoda H., Woo E.R., Lee K.B., Kim Y.S., Toida T., Imanari T. Carbohydrate Research, 2002, vol. 337, no. 10, pp. 925–933, DOI: 10.1016/S0008-6215(02)00078-2.

Fan L., Gao S., Wang L., Wu P., Cao M., Zheng H., Xie W., Zhou, J. Journal of Applied Polymer Science, 2012, vol. 124, pp. 2171–2178, DOI 10.1002/app.35239.

Dushkin A.V., Meteleva E.S., Tolstikova T.G., Tolstikov G.A., Polyakov N.E., Neverova N.A., Medvedeva E.N., Babkin V.A. Russian Chemical Bulletin, 2008, vol. 57, no. 6, pp. 1299–1307.

Patent 2319707 (RU). 20.03.2008. (in Russ.).

Shurygina I.A., Sukhov B.G., Fadeeva T.V., Umanets V.A., Shurygin M.G., Ganenko T.V., Kostyro Y.A., Grigo-riev E.G., Trofimov B.A. Nanomedicine: Nanotechnology, Biology and Medicine, 2011, vol. 7, no. 6, pp. 827–833, DOI: 10.1016/j.nano.2011.03.003.

Kostyro Ya.A., Koval'skaya G.N. Acta Biomedica Scientifica, 2008, vol. 60, no. 2, p. 117. (in Russ.).

Drozd N.N., Kuznetsova S.A., Lapikova Ye.S., Davydova A.I., Makarov V.A., Kuznetsov B.N., Butylkina A.I., Va-sil'yeva N.Yu., Skvortsova G.P. Eksperimental'naya i klinicheskaya farmakologiya, 2008, vol. 71, no. 4, pp. 30–34. (in Russ.).

Xu Y., Dong Q., Qiu H., Cong R., Ding K. Biomacromolecules, 2010, vol. 11, no. 10, pp. 2558–2566, DOI: 10.1021/bm100402n.

Dzhil'bert E.Ye. Sul'firovaniye organicheskikh soyedineniy. [Sulfonation of Organic Compounds]. Moscow, 1969, 416 p. (in Russ.).

Patent 101054420 (CN). 17.10.2007.

Patent 2466143 (RU). 10.11.2012. (in Russ.).

Patent 2521649 (RU). 10.07.2014. (in Russ.).

Patent 2546965 (RU). 10.04.2015. (in Russ.).

Vasil'yeva N.Yu., Levdanskiy A.V., Kuznetsov B.N., Skvortsova G.P., Kazachenko A.S., Djakovitch L., Pinel C. Khimiya rastitel'nogo syr'ya, 2014, no. 1, pp. 87–95, DOI: 10.14258/jcprm.1401087. (in Russ.).

Patent 2273646 (RU). 10.04.2006. (in Russ.).

Stuart R., Michel A. Canadian Medical Association Journal, 1971, vol. 104, no. 5, pp. 385–388.

Yin E., Wessler S., Butler J. Journal of Laboratory and Clinical Medicine, 1973, vol. 81, no. 2, pp. 298–310.

Makarov V.A., Spasov A.A., Plotnikov M.B., Belozeraskaya G.G., Vasil'yeva T.M., Drozd N.N., Svistunov A.A., Kucheryavenko A.F., Malykhina L.S., Naumenko L.V., Nevedrova O.Ye., Petrukhina G.N., Aliyev O.I., Plotniko-va T.M. Rukovodstvo po provedeniyu doklinicheskikh issledovaniy lekarstvennykh sredstv. [Guidelines for preclinical studies of drugs]. Moscow, 2012, pp. 453–479. (in Russ.).

Matsuhiro B. Hydrobiologia, 1996, vol. 326/327, no. 1, pp. 481–489, DOI: 10.1007/BF00047849.

Rosenberg R.D., Armand G., Lam L. Proceedings of the National Academy of Sciences USA, 1978, vol. 75, no. 7, pp. 3065–3069.

Madeira J.C., da Silva G.V.L., Batista J.J., Saraiva G.D., Santos G.R.C., Assreuy A.M.S., Mourão P.A.S., Perei-ra M.G. Carbohydrate Polymers, 2018, vol. 202, pр. 554–562, DOI: 10.1016/j.carbpol.2018.09.003.

Published
2019-12-27
How to Cite
1. Kuznetsova S. A., Vasilyeva N. Y., Drozd N. N., Mikhailenko M. A., Shakhtshneider T. P., Malyar Y. N., Kuznetsov B. N., Chesnokov N. V. SULFATED DERIVATIVES OF ARABINOGALACTAN AND THEIR ANTICOAGULANT ACTIVITY // chemistry of plant raw material, 2019. № 4. P. 47-56. URL: http://journal.asu.ru/cw/article/view/4845.
Section
Biopolymers of plants