Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity
The antiviral activity against herpes simplex virus types 1 and 2 of κ/l-, partially cyclized μ/v-, and λ-carrageenans isolated from the red seaweed Gigartina skottsbergii and their cyclized derivatives was analyzed. λ-Carrageenans and the partially cyclized μ/v-carrageenan were the most potent inhi...
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todo:paper_01418130_v20_n2_p97_Carlucci2023-10-03T14:58:44Z Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity Carlucci, M.J. Pujol, C.A. Ciancia, M. Noseda, M.D. Matulewicz, M.C. Damonte, E.B. Cerezo, A.S. Anti-herpes simplex virus activity Anticoagulant activity Carrageenan carrageenan disulfide galactose anticoagulation antiviral activity article chemical structure cytotoxicity herpes simplex virus 1 herpes simplex virus 2 seaweed Animals Anticoagulants Antiviral Agents Carbohydrate Sequence Carrageenan Cercopithecus aethiops Herpesvirus 1, Human Herpesvirus 2, Human Humans Macromolecular Substances Molecular Structure Molecular Weight Seaweed Structure-Activity Relationship Thrombin Time Vero Cells The antiviral activity against herpes simplex virus types 1 and 2 of κ/l-, partially cyclized μ/v-, and λ-carrageenans isolated from the red seaweed Gigartina skottsbergii and their cyclized derivatives was analyzed. λ-Carrageenans and the partially cyclized μ/v-carrageenan were the most potent inhibitors of herpes viruses (including acyclovir-resistant variants and clinical isolates), with IC50 values lower than 1 μg ml-1 against both serotypes and selectivity indices higher than 103. κ/l-Carrageenans were slightly less effective than the other two types with IC50 values in the range 1.6-4.1 μg ml-1. Antiherpetic activity was directly correlated to the amount of α-D-galactose 2,6-disulfate residues in the natural carrageenans. The cyclization of the α-D-galactose 6-sulfate and 2,6-disulfate units into 3,6-anhydro-α-D-galactose and 3,6-anhydro-α-D-galactose 2-sulfate residues in these polysaccharides, in general, lowers the antiherpetic activity of the derivatives with respect to the natural carrageenans. Some carrageenans showed a very reduced anticoagulant activity only at concentrations that were considerably higher than the IC50, whereas others were totally devoid of anticoagulant properties. Among natural carrageenans, the μ/v-type 1C3 shows the best relationship between antiviral efficacy and lack of anticoagulant action, resulting a very promising compound. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01418130_v20_n2_p97_Carlucci |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Anti-herpes simplex virus activity Anticoagulant activity Carrageenan carrageenan disulfide galactose anticoagulation antiviral activity article chemical structure cytotoxicity herpes simplex virus 1 herpes simplex virus 2 seaweed Animals Anticoagulants Antiviral Agents Carbohydrate Sequence Carrageenan Cercopithecus aethiops Herpesvirus 1, Human Herpesvirus 2, Human Humans Macromolecular Substances Molecular Structure Molecular Weight Seaweed Structure-Activity Relationship Thrombin Time Vero Cells |
| spellingShingle |
Anti-herpes simplex virus activity Anticoagulant activity Carrageenan carrageenan disulfide galactose anticoagulation antiviral activity article chemical structure cytotoxicity herpes simplex virus 1 herpes simplex virus 2 seaweed Animals Anticoagulants Antiviral Agents Carbohydrate Sequence Carrageenan Cercopithecus aethiops Herpesvirus 1, Human Herpesvirus 2, Human Humans Macromolecular Substances Molecular Structure Molecular Weight Seaweed Structure-Activity Relationship Thrombin Time Vero Cells Carlucci, M.J. Pujol, C.A. Ciancia, M. Noseda, M.D. Matulewicz, M.C. Damonte, E.B. Cerezo, A.S. Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity |
| topic_facet |
Anti-herpes simplex virus activity Anticoagulant activity Carrageenan carrageenan disulfide galactose anticoagulation antiviral activity article chemical structure cytotoxicity herpes simplex virus 1 herpes simplex virus 2 seaweed Animals Anticoagulants Antiviral Agents Carbohydrate Sequence Carrageenan Cercopithecus aethiops Herpesvirus 1, Human Herpesvirus 2, Human Humans Macromolecular Substances Molecular Structure Molecular Weight Seaweed Structure-Activity Relationship Thrombin Time Vero Cells |
| description |
The antiviral activity against herpes simplex virus types 1 and 2 of κ/l-, partially cyclized μ/v-, and λ-carrageenans isolated from the red seaweed Gigartina skottsbergii and their cyclized derivatives was analyzed. λ-Carrageenans and the partially cyclized μ/v-carrageenan were the most potent inhibitors of herpes viruses (including acyclovir-resistant variants and clinical isolates), with IC50 values lower than 1 μg ml-1 against both serotypes and selectivity indices higher than 103. κ/l-Carrageenans were slightly less effective than the other two types with IC50 values in the range 1.6-4.1 μg ml-1. Antiherpetic activity was directly correlated to the amount of α-D-galactose 2,6-disulfate residues in the natural carrageenans. The cyclization of the α-D-galactose 6-sulfate and 2,6-disulfate units into 3,6-anhydro-α-D-galactose and 3,6-anhydro-α-D-galactose 2-sulfate residues in these polysaccharides, in general, lowers the antiherpetic activity of the derivatives with respect to the natural carrageenans. Some carrageenans showed a very reduced anticoagulant activity only at concentrations that were considerably higher than the IC50, whereas others were totally devoid of anticoagulant properties. Among natural carrageenans, the μ/v-type 1C3 shows the best relationship between antiviral efficacy and lack of anticoagulant action, resulting a very promising compound. |
| format |
JOUR |
| author |
Carlucci, M.J. Pujol, C.A. Ciancia, M. Noseda, M.D. Matulewicz, M.C. Damonte, E.B. Cerezo, A.S. |
| author_facet |
Carlucci, M.J. Pujol, C.A. Ciancia, M. Noseda, M.D. Matulewicz, M.C. Damonte, E.B. Cerezo, A.S. |
| author_sort |
Carlucci, M.J. |
| title |
Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity |
| title_short |
Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity |
| title_full |
Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity |
| title_fullStr |
Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity |
| title_full_unstemmed |
Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity |
| title_sort |
antiherpetic and anticoagulant properties of carrageenans from the red seaweed gigartina skottsbergii and their cyclized derivatives: correlation between structure and biological activity |
| url |
http://hdl.handle.net/20.500.12110/paper_01418130_v20_n2_p97_Carlucci |
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