Synthesis of polymethacrylate derivatives having sulfated maltoheptaose side chains with anti‐HIV activities

Yoshida, Takashi; Akasaka, Tsukasa; Choi, Yoonsoung; Hattori, Katsumi; Yu, Bin; Mimura, Toru; Kaneko, Yutaro; Nakashima, Hideharu; Aragaki, Eriko; Premanathan, Mariappan; Yamamoto, Naoki; Uryu, Toshiyuki

doi:10.1002/(sici)1099-0518(19990315)37:6<789::aid-pola14>3.3.co;2-q

Cited by 23 publications

(33 citation statements)

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“…23 Similarly, partially sulfated poly(maltoheptaose methacrylate) exhibited HIV inhibitory potencies ranging from 66 to 0.3 µg·mL -1 for polymers ranging from 276000 -20000 g·mol -1 , respectively. 50 Interestingly, Kiser and co-workers described synergistic effects with a more than 2 log decrease in IC 50 with copolymers consisting of AMPS, benzoboroxole methacrylamide and N-2-hydroxypropyl methacrylamide. 21 While structural differences exist between the polymers made here compared to polymers assayed elsewhere, the main reason for the absence of inhibition potencies of the partially sulfonated polymers P13 -P15 and the lack of synergy of the sulfonated polymers with 3TC self-immolative linker (P8 -P12) up to 100 mg·L -1 against HIV remains to be investigated.…”

Section: Antiviral Activitymentioning

confidence: 99%

Triple Activity of Lamivudine Releasing Sulfonated Polymers against HIV-1

et al. 2016

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In this article a library of polymeric therapeutic agents against the human immunodeficiency virus (HIV) is presented. The library of statistical copolymers of varied molar mass was synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. The synthesized polymers comprise pendent hydroxyl and sulfonated side chains as well as the reverse transcriptase prodrug lamivudine (3TC) attached via a disulfide self-immolative linker. The glutathione mediated release of 3TC is demonstrated as well as the antiviral efficacy against HIV entry and polymerase activity. Although a high degree of polymer sulfonation is required for effective HIV entry inhibition, polymers with approximately ∼50% sulfonated monomer demonstrated potent kinase independent reverse transcriptase inhibition. In addition, the sulfonated polymers demonstrate activity against DNA-DNA polymerase, which suggests that these polymers may exhibit activity against a broad spectrum of viruses. In summary, the polymers described provide a triple-active arsenal against HIV with extracellular activity via entry inhibition and intracellular activity by kinase-dependent lamivudine-based and kinase-independent sulfonated polymer based inhibition. Since these sulfonated copolymers are easily formulated into gels, we envision them to be particularly suited for topical application to prevent the mucosal transmission of viruses, particularly HIV.

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Section: Antiviral Activitymentioning

confidence: 99%

Triple Activity of Lamivudine Releasing Sulfonated Polymers against HIV-1

et al. 2016

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“…Of potential application as tools in this new discipline are glycopolymers—synthetic macromolecules featuring pendant carbohydrate moieties. In this regard, glycopolymers have been investigated in diverse applications including, but not limited to, macromolecular drugs2–6 and drug delivery systems,7–10 biocatalytic11 and biosensitive12 hydrogels, matrices for controlled cell culture,13–15 stationary phases for chromatographic purposes,16 surface modifiers17, 18 and as models of biological systems19; many of these require polymers of controlled structure with respect to attributes such as molecular weight, glycosylation density, and position. The synthesis of glycopolymers is a vast area (Fig.…”

Section: Introductionmentioning

confidence: 99%

Recent advances in the synthesis of well‐defined glycopolymers

Spain

Gibson

Cameron

2007

J. Polym. Sci. A Polym. Chem.

235

208

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Glycopolymers are receiving increasing interest due to their application in areas, such as glycomics, medicine, biotechnology, sensors, and separation science. Consequently, new methods for their synthesis are constantly being developed, with an increasing emphasis on the preparation of well‐defined polymers and on the production of complex macromolecular architectures such as stars. This review covers recent developments in the synthesis of glycopolymers, with a particular emphasis on (i) the use of controlled radical polymerization to prepare well‐defined glycopolymers from unprotected monomers and (ii) postpolymerization modification strategies using reactive polymer precursors (including “click” reactions). Recent work on the production of glycosylated polypeptides, which are under investigation as mimics of naturally occurring glycoproteins, is also included. The authors offer some suggestions as to future developments and remaining challenges in this topical area of polymer chemistry. © 2007 Wiley Periodicals, Inc. J Polym Sci PartA: Polym Chem45: 2059–2072, 2007

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“…Malto‐oligosaccharide, which has been produced from starch as a raw material by an enzyme‐catalyzed biotransformation in recent years,37, 38 plays an important role in polymer chemistry as a segment with a high water solubility39–47 as well as the primer to initiate the potato phosphorylase‐catalyzed polymerization of glucose‐1‐phosphate providing amylose‐based materials 48–59. Thus, we have focused on the use of malto‐oligosaccharide, especially maltohexaose, as hydrophilic segments of the amphiphilic macromolecular architectures such as block copolymers,43, 46 star‐shaped PSt,44 and PSt microgels,47 using glycoconjugated vinyl monomer.…”

Section: Introductionmentioning

confidence: 99%

Polycomb group gene expression in the sea urchin

Gustafson

Wessel

2008

Developmental Dynamics

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Embryonic development in metazoan animals involves a remarkable degree of both genetic and epigenetic regulation. Polycomb group (PcG) genes are essential for initiation and maintenance of epigenetic developmental regulation. This report identified homologous PcG genes representing the core components of three known Polycomb repressive complexes in the sea urchin Strongylocentrotus purpuratus. Quantitative, temporal and spatial analyses revealed two significant aspects of their transcript expression during embryonic development. First, almost all showed a localized expression pattern in mesenchyme blastula and gastrula-stage embryos. As the embryo specifies its three germ layers, it may require it PcG genes transcripts to remain in localized stem cell populations, but turn-over in differentiating tissues. Second, their transcript levels gradually decreased during larval pluteus stages. This is consistent with progressive stem cell differentiation in the embryo. Taken together, these results suggest that PcG genes are conserved in S. purpuratus and are actively expressed during early embryogenesis.

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Synthesis of polymethacrylate derivatives having sulfated maltoheptaose side chains with anti‐HIV activities

Cited by 23 publications

References 0 publications

Triple Activity of Lamivudine Releasing Sulfonated Polymers against HIV-1

Triple Activity of Lamivudine Releasing Sulfonated Polymers against HIV-1

Recent advances in the synthesis of well‐defined glycopolymers

Polycomb group gene expression in the sea urchin

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