Fluorine-substituted tetracationic ABAB-phthalocyanines for efficient photodynamic inactivation of Gram-positive and Gram-negative bacteria

Self‐Assembled Binaphthyl‐Bridged Amphiphilic AABB Phthalocyanines: Nanostructures for Efficient Antimicrobial Photodynamic Therapy

“…[11][12][13][14][15] Worth of mention is that Pors bearing cationic groups in adjacent meso positions seem to be significantly more efficient than those with the cationic groups located in opposite meso positions. [16] Although cationic Pcs have been also stud-ied for PDI, in many cases using alkylpyridinium motifs, [17][18][19][20] only af ew reports can be found on the preparation and biological evaluation of asymmetric systemsw ith am ore pronounced amphiphilic character arising from the asymmetric distribution of substituents in an "AABB" fashion with Aa nd B coding for differently substituted isoindoles. [21,22] On the other hand, strongly cationic nanoparticles are known to interact more favorably with the cell membranes, thereby enhancing their intracellular uptake.…”

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

“…Separating the hydrophobic and hydrophilic parts of a Pc was explored using two differently functionalized isoindol units [59] . ABAB‐type Pcs functionalized with pyridines 33 or tertiary amines 34 were isolated and quaternized to achieve water solubility.…”

“…Separating the hydrophobic and hydrophilic parts of aP c was explored using two differently functionalized isoindol units. [59] ABAB-type Pcs functionalized with pyridines 33 or tertiary amines 34 were isolated and quaternized to achieve water solubility.M easurements of the singlet oxygen quantum yield by direct observation of the 1 O 2 phosphorescence at 1275 nm in methanols howedt hat 34 had al ower F D (0.35) than 33 (0.49). When comparing the aPDT activity on Grampositive S. aureus and Gram-negative E. coli upon red light irradiation (33 Jcm À2 ), 0.1 mm of 33 and 0.5 mm 34 were neededt o achievea3log reduction of S. aureus.…”

Assessing Amphiphilic ABAB Zn(II) Phthalocyanines with Enhanced Photosensitization Abilities in In Vitro Photodynamic Therapy Studies Against Cancer

“…For the preparation of our targeted Zn(II)Pcs, in particular ABAB-1 and A 3 B-1, endowed with bulky groups over B isoindole rings and hydrophilic TEG substituents over the A positions, we have performed cross-condensation reactions with the bulky phthalonitrile B, and either A-1-already containing the TEG moieties-or 4,5-bis(4-hydroxyphenoxy)phthalonitrile A-2 [23] (see Scheme 1). The latter approach, yielding the intermediate Zn(II)Pcs ABAB-2 and A 3 B-2 [24] that should be further O-alkylated, was tackled in the basis of previous studies, which had shown that the crossed condensation between B and A-2 is a highly efficient process (see below), and the Zn(II)Pcs formed are easily isolated from the reaction mixture [24].…”

“…,5,5"-tetrakis(trifluoromethyl)-[1,1 :4',1"-terphenyl]-2 ,3 -dicarbonitrile (B)[11], 4,5-bis(4hidroxiphenoxy)phthalonitrile (A-2)[23], 2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate (TEG-Ts)[25], and ABAB Zn(II)Pc 2[24], have been prepared according to published procedures. 4,5-bis-(4-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenoxy)phthalonitrile (A-1): In a two-neck round bottom flask, A-2 (150 mg, 0.44 mmol) and TEG-Ts (291 mg, 0.91 mmol) were solved in dry DMF (6 mL) and heated to 50 • C. Then, anhydrous K 2 CO 3 (199 mg, 1.44 mmol) was added in several portions.…”