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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1997
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01418130_v20_n2_p97_Carlucci http://hdl.handle.net/20.500.12110/paper_01418130_v20_n2_p97_Carlucci |
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paper:paper_01418130_v20_n2_p97_Carlucci2023-06-08T15:11:22Z Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity 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. 1997 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01418130_v20_n2_p97_Carlucci http://hdl.handle.net/20.500.12110/paper_01418130_v20_n2_p97_Carlucci |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
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 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. |
| 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 |
| publishDate |
1997 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01418130_v20_n2_p97_Carlucci http://hdl.handle.net/20.500.12110/paper_01418130_v20_n2_p97_Carlucci |
| _version_ |
1768545322912448512 |