Conjugation of cyclodextrin with fullerene as a new class of HCV entry inhibitors

Xiao, Sulong; Wang, Qi; Yu, Fei; Peng, Yiyun; Yang, Ming; Sollogoub, Matthieu; Sînaÿ, Pierre; Zhang, Yongmin; Zhang, Lihe; Zhou, Demin

doi:10.1016/j.bmc.2012.07.029

Cited by 29 publications

(23 citation statements)

References 16 publications

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“…We previously reported that α-CD-C60 conjugate (C7) inhibits HCV entry into the host cells with IC50 value of 0.17 µM [5]. In order to increase the family of α-CD-C60 conjugates, we designed and synthesized seven α-CD-C60 conjugates (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

“…However, the emergence of drug-resistant influenza viruses has limited the use of those drugs, illustrating the urgent need to develop novel anti-influenza drugs [2,3]. C60 serves as radical scavenger, reactive oxygen species (ROS) producer under irradiation, human immunodeficiency virus (HIV) and hepatitis C virus (HCV) inhibitors, O2 uptake inhibitor, drug and DNA vectors [4,5]. Nevertheless, its poor water-solubility limits the further development of C60.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and biological evaluation of water-soluble per-O-methylated cyclodextrin-C60 conjugates as anti-influenza virus agents

Zhu

Xiao

Zhou

et al. 2018

European Journal of Medicinal Chemistry

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. Design, synthesis and biological evaluation of water-soluble per-O -methylated cyclodextrin-C 60 conjugates as antiinfluenza virus agents. European Journal of Medicinal Chemistry, Elsevier, 2018, 146, pp.194 -205 E-mail: yongmin.zhang@upmc.fr Abstract:The most common fullerene member C60 displays many biological applications, such as, anticancer, human immunodeficiency virus and hepatitis C virus inhibitors, O2 uptake inhibitor and vectors for drug and DNA. Nevertheless, the innate hydrophobicity of C60 constrains its further development. We introduced cyclodextrins to enhance the water-solubility of C60. Nine cyclodextrin-C60 conjugates, including seven α-cyclodextrin-C60 conjugates and two γ-cyclodextrin-C60 conjugates, were designed and synthesized. All of these conjugates did not show obvious cytotoxicity. The anti-influenza virus activity of nine conjugates was assessed. Two γ-cyclodextrin-C60 conjugates, which were relatively more water-soluble, exerted higher inhibition with IC50 values of 87.73 µM and 75.06 µM, respectively, than seven α-cyclodextrin-C60 conjugates.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of water-soluble per-O-methylated cyclodextrin-C60 conjugates as anti-influenza virus agents

Zhu

Xiao

Zhou

et al. 2018

European Journal of Medicinal Chemistry

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“…[7d] Furthermore, sugar-,p rotein-,a nd polymerbased C 60 derivatives were applied as well. [7i-k] Some of us have synthesized af amily of CD-C 60 conjugates 1-9 (see Figure 1), [8][9][10][11][12] but in all cases aggregation was observed. They have been used as drug-carriers, precisely because they allow drug solubilization.…”

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confidence: 99%

“…Selective alkylationso r silylations have also been reported. [10,21,22] Therefore, we embarked in the implementation of this methodology on per-O-methylated g-CDs. [17][18][19] These strategies have been appliedt oa ll three a-, b-, and g-CDs, but the regioselectivities for g-CDs can be low because of their larger size.…”

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confidence: 99%

Secondary‐Rim γ‐Cyclodextrin Functionalization to Conjugate with C₆₀: Improved Efficacy as a Photosensitizer

Zhu

Quaranta

Bensasson

et al. 2017

Chemistry A European J

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DIBAL-H-mediated demethylation provides a novel method to access secondary-rim functionalized γ-cyclodextrin. 2 ,3 -Dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C allows access to the most water-soluble C conjugate described so far. The water solubility of 0.12 m (550 mg mL ) is 150 times higher than that of the native γ-CD/C complex. Its singlet oxygen ( O ) quantum yield is 0.39, an increase of one to two orders of magnitude compared to that of α(β)CD-C conjugates.

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“…76 In a more recent study, conjugation of cyclodextrin with fullerene structures displayed substantial inhibitors to the entry of the hepatitis C virus across membranes. 77 It is known that sugar moieties have important biological functions in cellular recognition, transport, and adhesion which may provide such conjugates with novel properties. Biological evaluations of fullerenols carrying mono-and bis-α-D-mannosyl linkages performed by Kato et al further elaborated this point.…”

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confidence: 99%

Fullerene–biomolecule conjugates and their biomedicinal applications

Yang¹,

Ebrahimi²,

et al. 2013

IJN

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Fullerenes are among the strongest antioxidants and are characterized as “radical sponges.” The research on biomedicinal applications of fullerenes has achieved significant progress since the landmark publication by Friedman et al in 1993. Fullerene–biomolecule conjugates have become an important area of research during the past 2 decades. By a thorough literature search, we attempt to update the information about the synthesis of different types of fullerene–biomolecule conjugates, including fullerene-containing amino acids and peptides, oligonucleotides, sugars, and esters. Moreover, we also discuss in this review recently reported data on the biological and pharmaceutical utilities of these compounds and some other fullerene derivatives of biomedical importance. While within the fullerene–biomolecule conjugates, in which fullerene may act as both an antioxidant and a carrier, specific targeting biomolecules conjugated to fullerene will undoubtedly strengthen the delivery of functional fullerenes to sites of clinical interest.

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Conjugation of cyclodextrin with fullerene as a new class of HCV entry inhibitors

Cited by 29 publications

References 16 publications

Design, synthesis and biological evaluation of water-soluble per-O-methylated cyclodextrin-C60 conjugates as anti-influenza virus agents

Design, synthesis and biological evaluation of water-soluble per-O-methylated cyclodextrin-C60 conjugates as anti-influenza virus agents

Secondary‐Rim γ‐Cyclodextrin Functionalization to Conjugate with C₆₀: Improved Efficacy as a Photosensitizer

Fullerene–biomolecule conjugates and their biomedicinal applications

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Conjugation of cyclodextrin with fullerene as a new class of HCV entry inhibitors

Cited by 29 publications

References 16 publications

Design, synthesis and biological evaluation of water-soluble per-O-methylated cyclodextrin-C60 conjugates as anti-influenza virus agents

Design, synthesis and biological evaluation of water-soluble per-O-methylated cyclodextrin-C60 conjugates as anti-influenza virus agents

Secondary‐Rim γ‐Cyclodextrin Functionalization to Conjugate with C60: Improved Efficacy as a Photosensitizer

Fullerene&ndash;biomolecule conjugates and their biomedicinal applications

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Secondary‐Rim γ‐Cyclodextrin Functionalization to Conjugate with C₆₀: Improved Efficacy as a Photosensitizer

Fullerene–biomolecule conjugates and their biomedicinal applications