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Synthesis, biophysical characterization and anti-HIV activity of d(TG(3)AG) Quadruplexes bearing hydrophobic tails at the 5 '-end (144 visite)

Romanucci V, Milardi D, Campagna T, Gaglione M, Messere A, D'Urso A, Crisafi E, La Rosa C, Zarrelli A, Balzarini J, Di Fabio G

Bioorg Med Chem (ISSN: 1464-3391, 0968-0896, 1464-3391electronic), 2014 Feb 1; 22(3): 960-966.

Tipo di articolo: Journal Article, Research Support, Non-U. S. Gov'T, , Impact factor: 2.793, Impact factor a 5 anni: 2.97, Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84892821971&partnerID=40&md5=c81760d31f7b35b00e2b458d16cd9321

Parole chiave: Anti-Hiv Activity, Aptamers, Conjugated Oligonucleotides, G-Quadruplex, Solid Phase Synthesis, Antivirus Agent, Conjugated G Quadruplex Forming Oligonucleotide, Guanine Quadruplex, Phosphoramidous Acid, Rna Directed Dna Polymerase, Unclassified Drug, Antiviral Activity, Article, Circular Dichroism, Controlled Study, Denaturation, Differential Scanning Calorimetry, Drug Conjugation, Drug Screening, Drug Stability, Drug Structure, Drug Synthesis, Human Immunodeficiency Virus 1, Lipophilicity, Nonhuman, Process Monitoring, Structure Activity Relation, Thermodynamics, Thermostability, Virus Inhibition, Anti-Hiv Agents, Cells, Cultured, Dose-Response Relationship, Drug Evaluation, Preclinical, Hiv Envelope Protein Gp120, Hiv Reverse Transcriptase, Hydrophobic And Hydrophilic Interactions, Serum Albumin, Solid-Phase Synthesis Techniques, Structure-Activity Relationship, Surface Plasmon Resonance, Anti-Hiv Agents Chemical Synthesis Chemistry Metabolism Pharmacology, Nucleotide Chemistry, Cultured Virology, Preclinical Methods, Hiv Envelope Protein Gp120 Metabolism, Hiv Envelope Protein Gp41 Metabolism, Hiv Reverse Transcriptase Antagonists, Inhibitors, Hiv-1 Drug Effects Pathogenicity, Hiv-2 Drug Effects Pathogenicity, Oligonucleotides Chemistry Pharmacology, Serum Albumin Metabolism,

Affiliazioni: *** IBB - CNR ***
Department of Chemical Sciences, University of Napoli 'Federico II', Via Cintia 4, I-80126 Napoli, Italy
Istituto di Biostrutture e Bioimmagini - Catania, Consiglio Nazionale Delle Ricerche, Viale Andrea Doria 6, 95125 Catania, Italy
Dipartimento di Scienze e Tecnologie Ambientali, Biologiche e Farmaceutiche, Seconda Università̀ di Napoli, Via Vivaldi 43, 81100 Caserta, Italy
Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium


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Novel conjugated G-quadruplex-forming d (TG (3) AG) oligonucleotides, linked to hydrophobic groups through phosphodiester bonds at 5'-end, have been synthesized as potential anti-HIV aptamers, via a fully automated, online phosphoramidite-based solid-phase strategy. Conjugated quadruplexes showed pronounced anti-HIV activity with some preference for HIV-1, with inhibitory activity invariably in the low micromolar range. The CD and DSC monitored thermal denaturation studies on the resulting quadruplexes, indicated the insertion of lipophilic residue at the 5'-end, conferring always improved stability to the quadruplex complex (20 < Delta Tm < 40 degrees C). The data suggest no direct functional relationship between the thermal stability and anti-HIV activity of the folded conjugated G-quartets. It would appear that the nature of the residue at 50 end of the d (TG (3) AG) quadruplexes plays an important role in the thermodynamic stabilization but a minor influence on the anti-HIV activity. Moreover, a detailed CD and DSC analyses indicate a monophasic behaviour for sequences I and V, while for ODNs (II-IV) clearly show that these quadruplex structures deviate from simple two-state melting, supporting the hypothesis that intermediate states along the dissociation pathway may exist. (C) 2014 Elsevier Ltd. All rights reserved
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15 Records (15 escludendo Abstract e Conferenze).
Impact factor totale: 72.457 (72.457 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 68.602 (68.602 escludendo Abstract e Conferenze).







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