Synthesis and Biological Uses of A₃B Type Water‐Soluble Phthalocyanine Alternate to Alcian Blue

Abstract

This study describes the synthesis and characterization of new non-symmetric cationic phthalocyanine derivatives and their capability for use in staining of microscopic normal and pathological tissue sections, polyacrylamide gel staining, and spectrophotometric analyses. These new synthesized compounds have specifically stained the glycosaminoglycans (GAGs) in the matrix of cartilage tissue of the trachea. In addition, the mucus produced by the stomach, the small intestine and the colon tissue were stained with non-symmetrical cationic phthalocyanines comparable to the Alcian Blue 8GX. In addition, the determination of GAGs and glycoproteins in polyacrylamide gels has also been evaluated. Besides, the usage of these compounds to spectrophotometrically measure GAGs in biological fluids was also investigated. We have found that 6 and 7 are good alternatives to Alcian Blue 8GX due to comparable staining performance and interaction with biological molecules, especially acidic components such as acidic GAGs and mucin. These dyes have good solubility with quaternary ammonium groups effecting their binding performance to biological molecules.

DNA interaction, cytotoxic and phototoxic properties of new water‐soluble zinc (II) phthalocyanines

“…Water‐soluble ionic DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ were synthesized by the reaction of DM‐C6‐Zn and o‐DM‐C6‐Zn with CH 3 ‐I in CHCl 3 . [ 20,21 ] The nitrile (–C ≡ N) vibration peak of o‐DM‐C6‐CN appeared at 2238 cm −1 . In the 1 H‐NMR spectrum of o‐DM‐C6‐CN, aromatic protons appeared at 8.31–6.14 ppm.…”

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

“…For example, Pcs with high solubility in water become bioactive substances and benefit from a wide variety of biological properties. In recent years, our group has focused on the synthesis and biological applications of water‐soluble phthalocyanines [18,27–30] …”

“…In recent years, our group has focused on the synthesis and biological applications of water-soluble phthalocyanines. [18,[27][28][29][30] The addition of ionic or non-ionic substituents to Pcs makes them biocompatible by providing water solubility. Substitution of ionic groups on Pcs provides advantages such as increased water solubility and reduced aggregation, as well as high singlet oxygen formation.…”

Pegylated metal-free and zinc(ii) phthalocyanines: synthesis, photophysicochemical properties andin vitrophotodynamic activities against head, neck and colon cancer cell lines

“…5 The most common method used to make Pcs biocompatible is based on the addition of hydrophilic or amphiphilic substituents to the periphery or the core of Pcs such as quaternized amines, pyridinium ions, carboxylates, sulfonates, phosphonates, hydroxyl groups, peptides, carbohydrates, and polyethylene glycol (PEG) groups. [6][7][8][9][10][11][12][13][14] Polyethylene glycols are hydrophilic, synthetic, and biocompatible polyether compounds with the general formula H-(O-CH 2 -CH 2 ) n -OH, which have a wide range of uses from biomedical and chemical applications to various fields of industry. 15 Some examples of Pcs containing PEG chains terminated with hydroxyl groups (PEGOH) and methyl ether groups (PEGOMe) have been previously reported.…”