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Abstract:

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.

Registro:

Documento: Artículo
Título:Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity
Autor:Carlucci, M.J.; Pujol, C.A.; Ciancia, M.; Noseda, M.D.; Matulewicz, M.C.; Damonte, E.B.; Cerezo, A.S.
Filiación:Laboratorio de Virología, Depto. de Quim. Biológica, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Depto. de Quim. Orgánica, CIHIDECAR-CONICET, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Departamento de Bioquímica, Setor de Cie. Biológicas, Univ. Federal do Paraná, Curitiba-PR, Brazil
Palabras clave: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
Año:1997
Volumen:20
Número:2
Página de inicio:97
Página de fin:105
DOI: http://dx.doi.org/10.1016/S0141-8130(96)01145-2
Título revista:International Journal of Biological Macromolecules
Título revista abreviado:INT. J. BIOL. MACROMOL.
ISSN:01418130
CODEN:IJBMD
CAS:Anticoagulants; Antiviral Agents; Carrageenan, 9000-07-1; Macromolecular Substances
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01418130_v20_n2_p97_Carlucci

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Citas:

---------- APA ----------
Carlucci, M.J., Pujol, C.A., Ciancia, M., Noseda, M.D., Matulewicz, M.C., Damonte, E.B. & Cerezo, A.S. (1997) . Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity. International Journal of Biological Macromolecules, 20(2), 97-105.
http://dx.doi.org/10.1016/S0141-8130(96)01145-2
---------- CHICAGO ----------
Carlucci, M.J., Pujol, C.A., Ciancia, M., Noseda, M.D., Matulewicz, M.C., Damonte, E.B., et al. "Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity" . International Journal of Biological Macromolecules 20, no. 2 (1997) : 97-105.
http://dx.doi.org/10.1016/S0141-8130(96)01145-2
---------- MLA ----------
Carlucci, M.J., Pujol, C.A., Ciancia, M., Noseda, M.D., Matulewicz, M.C., Damonte, E.B., et al. "Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity" . International Journal of Biological Macromolecules, vol. 20, no. 2, 1997, pp. 97-105.
http://dx.doi.org/10.1016/S0141-8130(96)01145-2
---------- VANCOUVER ----------
Carlucci, M.J., Pujol, C.A., Ciancia, M., Noseda, M.D., Matulewicz, M.C., Damonte, E.B., et al. Antiherpetic and anticoagulant properties of carrageenans from the red seaweed Gigartina skottsbergii and their cyclized derivatives: Correlation between structure and biological activity. INT. J. BIOL. MACROMOL. 1997;20(2):97-105.
http://dx.doi.org/10.1016/S0141-8130(96)01145-2