Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers
Sulfated glucopyranans having long alkyl groups were prepared by the ring-opening copolymerization of benzylated 1,6-anhydroglucopyranose with 3-O-octadecyl 1,6-anhydro-β-d-glucopyranose monomers, and subsequent deprotection and sulfation. Water-soluble sulfated glucopyranans with 2.8 and 4.7 mol% o...
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| Format: | Article |
| Language: | English |
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Wiley
2015-01-01
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| Series: | International Journal of Polymer Science |
| Online Access: | http://dx.doi.org/10.1155/2015/317420 |
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| author | Shiming Bai Davaanyam Budragchaa Shuqin Han Taisei Kanamoto Hideki Nakashima Takashi Yoshida |
| author_facet | Shiming Bai Davaanyam Budragchaa Shuqin Han Taisei Kanamoto Hideki Nakashima Takashi Yoshida |
| author_sort | Shiming Bai |
| collection | DOAJ |
| description | Sulfated glucopyranans having long alkyl groups were prepared by the ring-opening copolymerization of benzylated 1,6-anhydroglucopyranose with 3-O-octadecyl 1,6-anhydro-β-d-glucopyranose monomers, and subsequent deprotection and sulfation. Water-soluble sulfated glucopyranans with 2.8 and 4.7 mol% of 3-O-octadecyl group and lower molecular weights of M-n = 2.5 × 103–5.1 × 103 have potent anti-HIV activity at 0.05–1.25 μg/mL, even though sulfated polysaccharides with molecular weights below M-n = 6 × 103 had low anti-HIV activity. The interaction with poly-l-lysine as a model compound of proteins was analyzed by SPR, DSL, and zeta potential, indicating that the sulfated 3-O-octadecyl glucopyranans had high association and low dissociation rate constants, and the particle size increased after addition of poly-l-lysine. The anti-HIV activity was induced by electrostatic interaction between sulfate groups and amino groups of poly-l-lysine and by the synergistic effect of the hydrophobic long alkyl chain and hydrophilic sulfated group. |
| format | Article |
| id | doaj-art-9e21556cce044db691414e59cb657801 |
| institution | Kabale University |
| issn | 1687-9422 1687-9430 |
| language | English |
| publishDate | 2015-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | International Journal of Polymer Science |
| spelling | doaj-art-9e21556cce044db691414e59cb6578012025-02-03T01:03:21ZengWileyInternational Journal of Polymer Science1687-94221687-94302015-01-01201510.1155/2015/317420317420Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose MonomersShiming Bai0Davaanyam Budragchaa1Shuqin Han2Taisei Kanamoto3Hideki Nakashima4Takashi Yoshida5Department of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, JapanDepartment of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, JapanDepartment of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, JapanSt. Marianna University School of Medicine, Miyamae-ku, Kawasaki 216-8511, JapanSt. Marianna University School of Medicine, Miyamae-ku, Kawasaki 216-8511, JapanDepartment of Bio and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, JapanSulfated glucopyranans having long alkyl groups were prepared by the ring-opening copolymerization of benzylated 1,6-anhydroglucopyranose with 3-O-octadecyl 1,6-anhydro-β-d-glucopyranose monomers, and subsequent deprotection and sulfation. Water-soluble sulfated glucopyranans with 2.8 and 4.7 mol% of 3-O-octadecyl group and lower molecular weights of M-n = 2.5 × 103–5.1 × 103 have potent anti-HIV activity at 0.05–1.25 μg/mL, even though sulfated polysaccharides with molecular weights below M-n = 6 × 103 had low anti-HIV activity. The interaction with poly-l-lysine as a model compound of proteins was analyzed by SPR, DSL, and zeta potential, indicating that the sulfated 3-O-octadecyl glucopyranans had high association and low dissociation rate constants, and the particle size increased after addition of poly-l-lysine. The anti-HIV activity was induced by electrostatic interaction between sulfate groups and amino groups of poly-l-lysine and by the synergistic effect of the hydrophobic long alkyl chain and hydrophilic sulfated group.http://dx.doi.org/10.1155/2015/317420 |
| spellingShingle | Shiming Bai Davaanyam Budragchaa Shuqin Han Taisei Kanamoto Hideki Nakashima Takashi Yoshida Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers International Journal of Polymer Science |
| title | Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers |
| title_full | Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers |
| title_fullStr | Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers |
| title_full_unstemmed | Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers |
| title_short | Sulfated Alkyl Glucopyranans with Potent Antiviral Activity Synthesized by Ring-Opening Copolymerization of Anhydroglucose and Alkyl Anhydroglucose Monomers |
| title_sort | sulfated alkyl glucopyranans with potent antiviral activity synthesized by ring opening copolymerization of anhydroglucose and alkyl anhydroglucose monomers |
| url | http://dx.doi.org/10.1155/2015/317420 |
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