Studies on photoinactivation by various phthalocyanines of a free or replicating non-enveloped virus

Porphyrin-based cationic amphiphilic photosensitisers as potential anticancer, antimicrobial and immunosuppressive agents

“…Using electron microscopy, a massive destruction of virus envelopes was detected after treatment with phthalocyanines containing metal ligands, leading to a significant decrease of virus infectivity of several enveloped viruses [Varicella zoster virus (VZV), HSV-1 and HSV-2], whereas non-enveloped adenovirus was largely resistant to the treatment (Smetana et al 1994). Nevertheless, several studies have presented evidence that non-enveloped viruses are also sensitive to direct PACT inactivation (Kasturi and Platz 1992;Gaspard et al 1995;Costa et al 2008Costa et al , 2010Zupan et al 2008), which might be explained by photoactivated protein crosslinking that leads to direct damage or loss of proteins, and finally the loss of infectivity (Lenard et al 1993;Smetana et al 1997;Orosz et al 2013). At physiological conditions, non-enveloped viruses have negatively charged capsids and enveloped viruses harbour negatively charged glycoproteins on their surface, and are thus likely directly targeted by cationic porphyrins via electrostatic interactions, like previously described for Gram(−) bacteria (Karlin and Brendel 1988;Michen and Graule 2010;Liu et al 2015).…”

“…Nonetheless, to what extent such intercalation and cleavage contributes to virus inhibition in comparison to other possible mechanisms is not clear (Zupan et al 2005). Moreover, in addition to direct effect of PACT on virus structure and/or genetic material, intrinsic antiviral cellular mechanisms triggered by PACT are largely unknown (Gaspard et al 1995).…”

“…(Horowitz et al 1991;Rywkin et al 1992Rywkin et al , 1994Rywkin et al , 1995Gaspard et al 1995;Remichkova et al 2016;Rodrigues et al 2016b). In most of these studies, a significant decrease in virus infectivity was observed with a variety of different phthalocyanine derivatives.…”

“…The antiviral activity can be explained by photoactivated damage to endosomes early in the infection, along with damage to envelope proteins (Smetana et al 1998). On the other hand, cells treated prior to infection with different phthalocyanine derivatives, including CuPcS4, ZnPc(3-OPy)4 and ZnPc(3-MeO-Py)4, were completely refractory to non-enveloped Rhinovirus type 5(RV5) at non-toxic concentrations, and at the same time the compound was ineffective against a cell-free virus, which might indicate an undetermined intrinsic antiviral mechanism (Gaspard et al 1995). Obviously, more thorough analysis of cellular proteome and virus gene expression is needed to address and reveal the exact molecular mechanisms responsible for such inhibition.…”

Synthesis of new octakis(benzylthio)tetraazaporphyrin complexes with bivalent transition metal ions and an investigation of their spectral, redox and catalytic properties

“…Unlike their more common tetrapyrrolic congeners, the porphyrins and phthalocyanins, they offer a much higher potential for creating structural diversity. With the inherent synthetic ease of including diverse peripheral substituents, they are seen as promising materials having potential applications in diverse areas such as chemical sensors [10][11][12][13], biomedical diagnosis [14] and therapeutic reagents [15][16][17][18][19][20][21][22][23], optical data storage [24,25], non-linear optics [26][27][28] and liquid crystals. Metallo-tetraazaporphyrins are also useful in electrographic recording [29], making magnetic toner ink [30], in molecular photovoltaics [31,32] and in making optical light switches [33].…”