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Amphiphilic Heparinoids as Potent Antiviral Agents against SARS-CoV-2.
Chhabra, Mohit; Shanthamurthy, Chethan D; Kumar, Nanjudaswamy Vijendra; Mardhekar, Sandhya; Vishweshwara, Sharath S; Wimmer, Norbert; Modhiran, Naphak; Watterson, Daniel; Amarilla, Alberto A; Cha, Jonathan S; Beckett, James R; De Voss, James J; Kayal, Yasmin; Vlodavsky, Israel; Dorsett, Lauren R; Smith, Raymond A A; Gandhi, Neha S; Kikkeri, Raghavendra; Ferro, Vito.
Afiliación
  • Chhabra M; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Shanthamurthy CD; Australian Infectious Diseases Research Centre, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Kumar NV; Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune 411008, India.
  • Mardhekar S; Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune 411008, India.
  • Vishweshwara SS; Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune 411008, India.
  • Wimmer N; Indian Institute of Science Education and Research, Dr. Homi Bhabha Road, Pune 411008, India.
  • Modhiran N; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Watterson D; Australian Infectious Diseases Research Centre, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Amarilla AA; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Cha JS; Australian Infectious Diseases Research Centre, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Beckett JR; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • De Voss JJ; Australian Infectious Diseases Research Centre, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Kayal Y; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Vlodavsky I; Australian Infectious Diseases Research Centre, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Dorsett LR; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Smith RAA; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Gandhi NS; School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland 4072, Australia.
  • Kikkeri R; Technion Integrated Cancer Center (TICC), Rappaport Faculty of Medicine, Technion─Israel Institute of Technology, Haifa 31096, Israel.
  • Ferro V; Technion Integrated Cancer Center (TICC), Rappaport Faculty of Medicine, Technion─Israel Institute of Technology, Haifa 31096, Israel.
J Med Chem ; 67(14): 11885-11916, 2024 Jul 25.
Article en En | MEDLINE | ID: mdl-38995734
ABSTRACT
Herein, we report the synthesis and biological evaluation of a novel series of heparinoid amphiphiles as inhibitors of heparanase and SARS-CoV-2. By employing a tailor-made synthetic strategy, a library of highly sulfated homo-oligosaccharides bearing d-glucose or a C5-epimer (i.e., l-idose or l-iduronic acid) conjugated with various lipophilic groups was synthesized and investigated for antiviral activity. Sulfated higher oligosaccharides of d-glucose or l-idose with lipophilic aglycones displayed potent anti-SARS-CoV-2 and antiheparanse activity, similar to or better than pixatimod (PG545), and were more potent than their isosteric l-iduronic acid congeners. Lipophilic groups such as cholestanol and C18-aliphatic substitution are more advantageous than functional group appended lipophilic moieties. These findings confirm that fine-tuning of higher oligosaccharides, degree of sulfation, and lipophilic groups can yield compounds with potent anti-SARS-CoV-2 activity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antivirales / SARS-CoV-2 Límite: Animals / Humans Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Estados Unidos
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antivirales / SARS-CoV-2 Límite: Animals / Humans Idioma: En Revista: J Med Chem Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Estados Unidos