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

Abstract

The synthesis and characterization of axially bis(1,2,2,6,6-pentamethyl-4-piperidinol) silicon(IV) phthalocyanine (3) and its water-soluble cationic derivative (3Q) were defined in this study. Both newly synthesized silicon(IV) phthalocyanines were characterized by FT-IR, UV-Vis, 1 H NMR, MALDI-TOF and elemental analysis as well. Although the photophysical and photochemical properties of newly synthesized axially bis(1,2,2,6,6-pentamethyl-4-piperidinol) silicon(IV) phthalocyanine was investigated in DMSO, its water-soluble derivative was investigated in both DMSO and phosphate buffer saline (PBS). The fluorescence quenching behavior of the studied water-soluble silicon(IV) phthalocyanine (3Q) by the addition of 1,4-benzoquinone (BQ) was also described in DMSO. Besides, the binding behavior of 3Q, it was examined by bovine serum albumin (BSA) protein in PBS for determination of transportation abilities of this phthalocyanine in the blood. Photodynamic activity of water-soluble silicon(IV) phthalocyanine (3Q) was tested in vitro on tumor cells and for inactivation of bacterial pathogens with promising photocytotoxicity for both PDT applications.

Turning Photons into Drugs: Phthalocyanine‐Based Photosensitizers as Efficient Photoantimicrobials

“…For Gram‐negative P. aeruginosa , the effect was negligible for concentrations up to 22 μ m of 5 b and a light dose 100 J cm −2 . The same strategy was used to coordinate (1,2,2,6,6‐ pentamethyl‐4‐piperidinol) into the axial positions of the SiPc 6 a ( Φ Δ =0.31 in DMSO), which was further quaternized to yield the water‐soluble derivative 6 b ( Φ Δ =0.18 in DMSO and Φ Δ =0.15 in phosphate‐buffered saline) [24] . Compared to 5 b , a lower concentration of 6 b (3–5 μ m ) was required to inactivate Gram‐positive S. mutans and S. aureus .…”

The effect of silicon phthalocyanine on cell death and mitochondrial membrane potential in pancreatic cancer cells

“…Axially substituted phthalocyanines are much less likely to aggregate because of steric hindrance of the nonplanar substituents to the central atom [6][7][8][9][10] that is why axially 1-benzyl-4-oxy units substituted silicon phthalocyanines has been chosen in this work (Fig. 1).…”

Synthesis of nonperipherally tetra-[5-(diethylamino)-2-formylphenoxy] substituted metallophthalocyanines and their electrochemistry

“…In addition, their unique electronic and chemical properties, physical and optical properties, as well as their chemical flexibility of phthalocyanines allow preparation of variety of related structures and diverse applications ranging from industrial to biological areas [3,4]. Phthalocyanines have been used in different areas such as photodynamic therapy [5,6], nonlinear optical materials [7], electrochemical sensors [8,9], biosensors [10], solar cells [11,12], light-emitting decives [13], liquid crystals [14], electrocatalyts [15], electropolymerization [16,17]. The solubility of unsubstituted phthalocyanines is very low in organic solvents.…”