Synthesis, Photophysical and Photochemical Properties of a Set of Silicon Phthalocyanines Bearing Anti-Inflammatory Groups

Abstract

In this study, a series of novel silicon (IV) phthalocyanines conjugated axially with anti-inflammatory (sulindac) and triethylene glycol groups has been synthesized. Different synthetic strategies were attempted to obtain the targeted molecules in high yield. The compounds were fully characterized by using different analyses techniques. Our objectives were to generate a system with sulindac group which enhances the singlet oxygen generation and exhibits anti-cancer effect. Therefore, photophysical and photochemical properties of these compounds were investigated in different solvents. The substituent effect on fluorescence quantum yield and singlet oxygen generation was evaluated for efficiency in photodynamic therapy (PDT) as photosensitizer. The molecules exhibited no aggregation tendency, solubility in common organic solvents, high singlet oxygen quantum yield and high photostability in DMSO so these favourable properties make them good candidates as photosensitizer for PDT. In addition, their stabilities were investigated in DMSO, THF, acetonitrile and DMF.

Novel axially symmetric and unsymmetric silicon(iv) phthalocyanines having anti-inflammatory groups: synthesis, characterization and their biological properties

“…Starting compounds, SiCl 2 Pc , 44,45 Si(OH) 2 Pc ( 4 ), 44,45 and polyoxo-SiPc ( 3 ) 46–48 were synthesized according to the literature. The synthesis, characterization and obtained spectral data of 3 are presented in the supplementary file (Fig.…”

“…Starting compounds, SiCl 2 Pc, 44,45 Si(OH) 2 Pc (4), 44,45 and polyoxo-SiPc (3) [46][47][48] were synthesized according to the litera-…”

A Translational Study of a Silicon Phthalocyanine Substituted with a Histone Deacetylase Inhibitor for Photodynamic Therapy

“…On the other hand, IC 50 values for Polyoxo-SiPc , (Figure S6a), which was used as a positive control that does not contain HDACi moieties, were calculated to be 45.6, 69.1, and 89.3 μM for HUVECs, MCF-7, and MDA-MB-231 cells, respectively, and bar graphics are given in Figure S6b.…”

“…Starting compounds SiCl 2 Pc , , HDACi (1-(2-methyl-(1,1′-biphenylmethyl))-3-hydroxyoxypyridin-2-thione), and Polyoxo-SiPc , were synthesized according to the literature. Data regarding synthesis and characterization of HDACi and Polyoxo-SiPc were given in the Supporting Information (Figures S8–S19 and Figures 20–23, respectively).…”

Novel Water-Soluble Silicon(IV) Phthalocyanine for Photodynamic Therapy and Antimicrobial Inactivations

“…[18] b Data from Ref. [19] (5.27 ns and 4.94 ns) in DMSO and PBS were obtained by the time correlated single photon counting (TCSPC) technique by fitting the fluorescence decay data to a mono exponential function (Table 2 and Figure 4).…”