Display options
Cite
Dohi H, Kanazawa T, Saito A, et al. Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family. Beilstein J Org Chem. 2014;10:1504-12doi: 10.3762/bjoc.10.155.
Dohi, H., Kanazawa, T., Saito, A., Sato, K., Uzawa, H., Seto, Y., & Nishida, Y. (2014). Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family. Beilstein journal of organic chemistry, 101504-12. https://doi.org/10.3762/bjoc.10.155
Dohi, Hirofumi, et al. "Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family." Beilstein journal of organic chemistry vol. 10 (2014): 1504-12. doi: https://doi.org/10.3762/bjoc.10.155
Dohi H, Kanazawa T, Saito A, Sato K, Uzawa H, Seto Y, Nishida Y. Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family. Beilstein J Org Chem. 2014 Jul 03;10:1504-12. doi: 10.3762/bjoc.10.155. eCollection 2014. PMID: 25161707; PMCID: PMC4142837.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2014 Jul 03;10:1504-12. doi: 10.3762/bjoc.10.155. eCollection 2014.

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family.

Beilstein journal of organic chemistry

Hirofumi Dohi, Takeru Kanazawa, Akihiro Saito, Keita Sato, Hirotaka Uzawa, Yasuo Seto, Yoshihiro Nishida

Affiliations

  1. Department of Nanobiology, Graduate School of Advanced Integration Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
  2. Department of Materials and Life Science, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan.
  3. National Research Institute of Police Science, 6-3-1 Kashiwanoha, Kashiwa, Chiba 277-0882, Japan.
  4. Nanosystem Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), 1-1-1 Higashi, Tsukuba, 305-8565, Japan.

PMID: 25161707 PMCID: PMC4142837 DOI: 10.3762/bjoc.10.155

Abstract

Glycosyl-[60]fullerenes were first used as decontaminants against ricin, a lactose recognition proteotoxin in the Ricinus communis family. A fullerene glycoconjugate carrying two lactose units was synthesized by a [3 + 2] cycloaddition reaction between C60 and the azide group in 6-azidohexyl β-lactoside per-O-acetate. A colloidal aqueous solution with brown color was prepared from deprotected bis(lactosyl)-C60 and was found stable for more than 6 months keeping its red color. Upon mixing with an aqueous solution of Ricinus communis agglutinin (RCA120), the colloidal solution soon caused precipitations, while becoming colorless and transparent. In contrast, a solution of concanavalin A (Con A) caused no apparent change, indicating that the precipitation was caused specifically by carbohydrate-protein interactions. This notable phenomenon was quantified by means of sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE), and the results were discussed in terms of detection and decontamination of the deadly biological toxin in the Ricinus communis family.

Keywords: fullerene; multivalent glycosystems; oligosaccharides; proteotoxins; ricin

References

  1. Biochemistry. 1972 Dec 19;11(26):4910-9 - PubMed
  2. Chem Biodivers. 2004 Oct;1(10):1452-64 - PubMed
  3. Chem Biodivers. 2005 Sep;2(9):1232-41 - PubMed
  4. J Med Chem. 2002 Jan 3;45(1):90-8 - PubMed
  5. Protein Sci. 1994 Feb;3(2):166-75 - PubMed
  6. Bioorg Med Chem. 1999 Sep;7(9):2053-62 - PubMed
  7. J Biol Chem. 1987 Jun 25;262(18):8834-9 - PubMed
  8. J Biol Chem. 1987 Apr 25;262(12):5908-12 - PubMed
  9. Curr Opin Struct Biol. 2000 Dec;10(6):680-6 - PubMed
  10. Glycoconj J. 2000 Jul-Sep;17(7-9):543-51 - PubMed
  11. J Biol Chem. 1987 Dec 15;262(35):17088-91 - PubMed
  12. ACS Appl Mater Interfaces. 2010 Apr;2(4):1081-5 - PubMed
  13. ACS Appl Mater Interfaces. 2012 Feb;4(2):832-7 - PubMed
  14. Analyst. 2008 May;133(5):626-34 - PubMed
  15. J Biol Chem. 1987 Apr 15;262(11):5398-403 - PubMed
  16. Carbohydr Res. 2002 Jun 5;337(11):983-9 - PubMed
  17. Chem Soc Rev. 2013 Jun 7;42(11):4613-22 - PubMed
  18. Angew Chem Int Ed Engl. 2012 Jul 27;51(31):7812-6 - PubMed
  19. Chem Soc Rev. 2013 Jun 7;42(11):4709-27 - PubMed
  20. Chem Soc Rev. 2013 Jun 7;42(11):4728-45 - PubMed
  21. Angew Chem Int Ed Engl. 1998 Nov 2;37(20):2754-2794 - PubMed
  22. Bioorg Med Chem Lett. 2001 Nov 19;11(22):2935-9 - PubMed

Publication Types