Liposomal Formulations of Novel BODIPY Dimers as Promising Photosensitizers for Antibacterial and Anticancer Treatment.

Synthesis, photochemical properties, liposomal encapsulation, and in vitro photodynamic activity studies of novel BODIPY dimer connected at positions and its brominated and iodinated analogs were described. UV-Vis measurements indicated that the dimeric structure of obtained BODIPYs did not significantly influence the positions of the absorption maxima. Emission properties and singlet oxygen generation studies revealed a strong heavy atom effect of brominated and iodinated BODIPY dimers, manifested by fluorescence intensity reduction and increased singlet oxygen generation ability compared to analog without halogen atoms.

Microwave-assisted synthesis, photochemical and electrochemical studies of long-wavelength BODIPY dyes.

Novel BODIPY derivatives possessing different styryl substituents were synthesized using different methods of Knoevenagel-type condensation with conventional heating and microwave radiation in two conditions. Microwave-assisted synthesis significantly reduces reaction time while enhancing its efficiency. The introduction of styryl substituents at the 3 and 5 positions of the BODIPY core resulted in a substantial bathochromic shift, which was affected by the substituents within styryl groups.

Synthesis, Electrochemical and Photochemical Properties of Sulfanyl Porphyrazine with Ferrocenyl Substituents.

Ferrocene is useful in modern organometallic chemistry due to its versatile applications in material sciences, catalysis, medicinal chemistry, and diagnostic applications. The ferrocene moiety can potentially serve many purposes in therapeutics and diagnostics. In the course of this study, (6-bromo-1-oxohexyl)ferrocene was combined with dimercaptomaleonitrile sodium salt to yield a novel maleonitrile derivative.

Improved Electrochemical Hydrogen Peroxide Detection Using a Nickel(II) Phthalimide-Substituted Porphyrazine Combined with Various Carbon Nanomaterials.

A metal-free porphyrazine derivative with peripheral phthalimide substituents was metallated with a nickel(II) ion. The purity of the nickel macrocycle was confirmed using HPLC, and characterized by MS, UV-VIS, and 1D (H, C) and 2D (H-C HSQC, H-C HMBC, H-H COSY) NMR techniques. The novel porphyrazine was combined with various carbon nanomaterials, such as carbon nanotubes-single walled (SWCNTs) and multi-walled (MWCNTs), and electrochemically reduced graphene oxide (rGO), to create hybrid electroactive electrode materials.

Chitosan Composites Containing Boron-Dipyrromethene Derivatives for Biomedical Applications.

The work is devoted to preparing and characterizing the properties of photosensitive composites, based on chitosan proposed for photodynamic therapy. Chitosan films with a 5% addition of two BODIPY dyes were prepared by solution casting. These dyes are dipyrromethene boron derivatives with N-alkyl phthalimide substituent, differing in the presence of iodine atoms in positions 2 and 6 of the BODIPY core.

Liposomal Nanoformulation as a Carrier for Curcumin and pEGCG-Study on Stability and Anticancer Potential.

Nanoformulations are regarded as a promising tool to enable the efficient delivery of active pharmaceutical ingredients to the target site. One of the best-known and most studied nanoformulations are liposomes-spherical phospholipid bilayered nanocarriers resembling cell membranes. In order to assess the possible effect of a mixture of polyphenols on both the stability of the formulation and its biological activity, two compounds were embedded in the liposomes-(i) curcumin (CUR), (ii) a peracetylated derivative of (-)-epigallocatechin 3--gallate (pEGCG), and (iii) a combination of the aforementioned.

Tuning Photodynamic Properties of BODIPY Dyes, Porphyrins' Little Sisters.

The photodynamic properties of a series of non-halogenated, dibrominated and diiodinated BODIPYs with a phthalimido or amino end modification on the phenoxypentyl and phenoxyoctyl linker in the position were investigated. Halogen substitution substantially increased the singlet oxygen production based on the heavy atom effect. This increase was accompanied by a higher photodynamic activity against skin melanoma cancer cells SK-MEL-28, with the best compound reaching an EC = 0.

Photochemical Properties and Stability of BODIPY Dyes.

The present study is devoted to the combined experimental and theoretical description of the photophysical properties and photodegradation of the new boron-dipyrromethene (BODIPY) derivatives obtained recently for biomedical applications, such as bacteria photoinactivation (Piskorz et al., Dyes and Pigments 2020, 178, 108322). Absorption and emission spectra for a wide group of solvents of different properties for the analyzed BODIPY derivatives were investigated in order to verify their suitability for photopharmacological applications.

BODIPY-Based Photosensitizers as Potential Anticancer and Antibacterial Agents: Role of the Positive Charge and the Heavy Atom Effect.

Boron-dipyrromethene derivatives, including cationic and iodinated analogs, were obtained and subjected to physicochemical and in vitro photodynamic activity studies. Iodinated derivatives revealed a substantial heavy atom effect manifested by a bathochromic shift of the absorption band by about 30 nm and fluorescence intensity reduced by about 30-35 times, compared to that obtained for non-iodinated ones. In consequence, singlet oxygen generation significantly increased with Φ values in the range 0.

Photocytotoxicity of liposomal zinc phthalocyanine in oral squamous cell carcinoma and pharyngeal carcinoma cells.

Photodynamic therapy utilizes a light-sensitive molecule that produces reactive oxygen species following irradiation. Photodynamic activities of free Zn phthalocyanine (ZnPc) and its liposomal formulations on human oral squamous cell carcinoma and pharyngeal carcinoma cells were assessed. ZnPc was incorporated in extruded and nonextruded liposomes composed of palmitoyloleoylphosphatidylglycerol (POPG):palmitoyloleoylphosphatidylcholine (POPC) or POPG:dioleoylphosphatidylethanolamine liposomes and incubated with CAL 27 or FaDu cells.

S-seco-porphyrazine as a new member of the seco-porphyrazine family - Synthesis, characterization and photocytotoxicity against cancer cells.

An important subgroup within the porphyrazine (Pz) family constitutes seco-porphyrazines, in the chemical structure of which one pyrrole unit is opened in the oxidative process. So far, there are only limited data on N-seco- and C-seco-Pzs. Here, the synthesis of a novel member of the Pzs seco-family, represented by an S-seco-tribenzoporphyrazine analogue, 22,23-bis(4-(3,5-dibutoxycarbonylphenoxy)butylsulfanyl)tribenzo[b,g,l]-22,23-dioxo-22,23-seco-porphyrazinato magnesium(II), is reported, with moderate 34% yield.

Porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria.

The multi-drug resistant bacteria have become a serious problem complicating therapies to such a degree that often the term "post-antibiotic era" is applied to describe the situation. The infections with methicillin-resistant S. aureus, vancomycin-resistant E.

Photodynamic therapy of cancer with liposomal photosensitizers.

The photodynamic reaction involves the light-induced generation of an excited state in a photosensitizer molecule (PS), which then results in the formation of reactive oxygen species in the presence of oxygen, or a direct modification of a cellular molecule. Most PSs are porphyrinoids, which are highly lipophilic, and are administered usually in liposomes to facilitate their effective delivery to target cells. The currently available liposomal formulations are Visudyne and Fospeg.

Liposomal formulations of magnesium sulfanyl tribenzoporphyrazines for the photodynamic therapy of cancer.

Photodynamic therapy of cancer comprises the activation of photosensitizer molecules delivered to cancer cells, to generate reactive oxygen species that mediate cytotoxicity. In this study, previously synthesized dendritic magnesium tribenzoporphyrazines were incorporated into four types of liposomes containing either 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) or 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) as the zwitterionic lipids. The addition of either l-α-phosphatidyl-dl-glycerol (PG) or 1,2-dioleoyl-3-trimethylammoniumpropane (DOTAP) imparted a negative or positive charge, respectively.

Photophysical properties and photocytotoxicity of free and liposome-entrapped diazepinoporphyrazines on LNCaP cells under normoxic and hypoxic conditions.

5,7-Diaryl-substituted symmetrical diazepinoporphyrazine and tribenzodiazepinoporphyrazine were synthesized and characterized using UV-Vis, MS MALDI, and various NMR techniques. The expected photosensitizing potentials of these porphyrazines were evaluated by measuring their abilities to generate singlet oxygen in organic solvents and by comparing them with that of the recently obtained dendrimeric G1-type diazepinoporhyrazine. Absorbance and fluorescence measurements were performed to study the aggregation properties of the novel macrocycles.

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico-Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy.

Sulfanyl porphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The presence of a dendrimeric periphery enhanced the spectral properties of the porphyrazines studied. The singlet-oxygen-generation quantum yield of the obtained macrocycles ranged from 0.

Diazepinoporphyrazines containing peripheral styryl substituents and their promising nanomolar photodynamic activity against oral cancer cells in liposomal formulations.

The photochemical properties and photodynamic activity of three porphyrazines (Pzs) containing annulated diazepine rings, including novel demetalated porphyrazine-possessing bis(styryl)diazepine moieties were investigated. The porphyrazines were evaluated in terms of their electronic absorption and emission properties, their tendency to undergo aggregation and photodegradation, as well as their singlet oxygen generation efficiency. The in vitro photodynamic activity of the porphyrazines and their liposomal formulations were examined by using two oral squamous cell carcinoma cell lines.

Current status of liposomal porphyrinoid photosensitizers.

The complete eradication of various targets, such as infectious agents or cancer cells, while leaving healthy host cells untouched, is still a great challenge faced in the field of medicine. Photodynamic therapy (PDT) seems to be a promising approach for anticancer treatment, as well as to combat various dermatologic and ophthalmic diseases and microbial infections. The application of liposomes as delivery systems for porphyrinoids has helped overcome many drawbacks of conventional photosensitizers and facilitated the development of novel effective photosensitizers that can be encapsulated in liposomes.