Synthesis of New Modified with Rhodamine B Peptides for Antiviral Protection of Textile Materials.

Petar Todorov,Petar Grozdanov,Ivo Grabchev,Ivanka Nikolova,Petia Peneva,Desislava Staneva,Stela Georgieva

doi:10.3390/molecules26216608

Abstract

Here we report on the synthesis and characterization of three new N-modified analogues of hemorphin-4 with rhodamine B. Modified with chloroacetyl, chloride cotton fabric has been dyed and color coordinates of the obtained textile materials were determined. Antiviral and virucidal activities of both the peptide-rhodamine B compounds and the dyed textile material were studied. Basic physicochemical properties (acid-base behavior, solvent influence, kinetics) related to the elucidation of structural activity of the new modified peptides based on their steric open/closed ring effect were studied. The obtained results lead to the conclusion that in protic solvent with change in pH of the environment, direct control over the dyeing of textiles can be achieved. Both the new hybrid peptide compounds and the modification of functionalized textile materials with these bioactive hemorphins showed virucidal activity against the human respiratory syncytial virus (HRSV-S2) and human adenovirus serotype 5 (HAdV-5) for different time intervals (30 and 60 min) and the most active compound was Rh-3.

Highlights

The xanthene dyes are widely used in medicinal and bioorganic chemistry as biologically active compounds
We have synthesized and characterized new rhodamine B-conjugated hemorphin-4 analogues as a potential sensitive fluorescent probe for color, antiviral, and virucidal activity of textile materials
We have explored an approach to the structural features of pH-dependent equilibrium between the spirolactam form and the ring-opened form of these peptides, the potential antiviral and virucidal activities of both of the new hybrid peptide molecules, and the modification of functionalized cotton fabrics with these bioactive hemorphins

Summary

Introduction

The xanthene dyes are widely used in medicinal and bioorganic chemistry as biologically active compounds (either alone or conjugated). These compounds possess potent antiviral activity against a human foreskin fibroblast (vesicular stomatitis virus) and enhance the antiviral activity of xanthene derivatives from 8- to 15-fold [1]. Rhodamine B derivatives represent an important tool for studies of more complex biochemical processes and activities. Such kind of fluorescence-based probes of bioactive molecules possess desirable features; they have an excellent spectral characteristics and relatively facile syntheses [2,3]. The only drawback to the use of rhodamine B is the formation of a spirolactam compound, which is non-fluorescent and cannot be used for all fluorescent microscopic applications [6]

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