3,7‐Bis(<i>N</i>‐methyl‐<i>N</i>‐phenylamino)phenothiazinium Salt: Improved Synthesis and Aggregation Behavior in Solution

Tiravia, Martina; Sabuzi, Federica; Cirulli, Martina; Pezzola, Silvia; Carmine, Graziano Di; Cicero, Daniel O.; Floris, Barbara; Galloni, Pierluca

doi:10.1002/ejoc.201900504

Cited by 10 publications

(12 citation statements)

References 55 publications

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“…The structural diversity of these derivatives remains low despite their high potential. The main approaches to the introduction of arylamine fragments into the structure of phenothiazine are the Buchwald-Hartwig reaction [ 18 , 27 , 28 ] and the oxidation of phenothiazine to phenothiazin-5-ium cation followed by nucleophilic addition of aromatic amines ( Scheme 1 ) [ 17 , 21 , 25 , 29 ].…”

Section: Resultsmentioning

confidence: 99%

“…The distance between the planes of the heterocycles is 3.5 Å ( Figure 3 ). The geometry of the H-dimer of PTZ1 is similar to that of the H-dimer of MB [ 21 ].…”

Section: Resultsmentioning

confidence: 99%

“…It turned out in a study of the effect of aromatic substituents of phenothiazine on aggregation ability that arylamine substituents at positions 3 and 7 of phenothiazine can inhibit aggregation ability. [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

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Arylamine Analogs of Methylene Blue: Substituent Effect on Aggregation Behavior and DNA Binding

Khadieva

Mostovaya

Padnya

et al. 2021

IJMS

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The synthesis of new phenothiazine derivatives, analogs of Methylene Blue, is of particular interest in the design of new drugs, as well as in the development of a new generation of agents for photodynamic therapy. In this study, two new derivatives of phenothiazine, i.e., 3,7-bis(4-aminophenylamino)phenothiazin-5-ium chloride dihydrochloride (PTZ1) and 3,7-bis(4-sulfophenylamino)phenothiazin-5-ium chloride (PTZ2), are synthesized for the first time and characterized by NMR, IR spectroscopy, HRMS and elemental analysis. The interaction of the obtained compounds PTZ1 and PTZ2 with salmon sperm DNA is investigated. It is shown by UV-Vis spectroscopy and DFT calculations that substituents in arylamine fragments play a crucial role in dimer formation and interaction with DNA. In the case of PTZ1, two amine groups promote H-aggregate formation and DNA interactions through groove binding and intercalation. In the case of PTZ2, sulfanilic acid fragments prevent any dimer formation and DNA binding due to electrostatic repulsion. DNA interaction mechanisms are studied and confirmed by UV-vis and fluorescence spectroscopy in comparison with Methylene Blue. The obtained results open significant opportunities for the development of new drugs and photodynamic agents.

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Section: Resultsmentioning

confidence: 99%

“…The distance between the planes of the heterocycles is 3.5 Å ( Figure 3 ). The geometry of the H-dimer of PTZ1 is similar to that of the H-dimer of MB [ 21 ].…”

Section: Resultsmentioning

confidence: 99%

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Arylamine Analogs of Methylene Blue: Substituent Effect on Aggregation Behavior and DNA Binding

Khadieva

Mostovaya

Padnya

et al. 2021

IJMS

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“…Results revealed that B3LYP and CAM-B3LYP better represent the absorption spectrum of 1H 2 in EtOH. Therefore, it can be assumed that WB97XD functional is suitable when a positive charge is delocalized over a π system, as previously observed [39,42]. Conversely, if the cation is located at the terminal position of a saturated alkyl side chain, and there is no interaction with the π-core, as in 1H 2 porphyrin, conventional functionals can be adopted.…”

Section: Resultsmentioning

confidence: 99%

Amphiphilic Porphyrin Aggregates: A DFT Investigation

et al. 2019

Self Cite

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Owing to the attractive potential applications of porphyrin assemblies in photocatalysis, sensors, and material science, studies presently concerning porphyrin aggregation are widely diffused.π-π stacking, H-bonding, metal coordination, hydrophobic effect, and electrostatic forces usually drive porphyrin interaction in solution. However, theoretical studies of such phenomena are still limited.Therefore, a computational examination of the different porphyrin aggregation approaches is proposed here, taking into account amphiphilic [5-{4-(3-trimethylammonium)propyloxyphenyl}-10,15,20-triphenylporphyrin] chloride, whose aggregation behavior has been previously experimentally investigated. Different functionals have been adopted to investigate the porphyrin dimeric species, considering long-range interactions. Geometry optimization has been performed, showing that for the compound under analysis, H-type and cation-π dimers are the most favored structures that likely co-exist in aqueous solution. Of note, frontier orbital delocalization showed an interesting interaction between the porphyrin units in the dimer at the supramolecular level.

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“…Meanwhile, spontaneous aggregation and limited solubility of the monomeric dyes affects the regularity of the polymer films obtained and the reproducibility of the modifier properties. Further improvement of the analytical and operational characteristics of electrochemical sensors calls for searching for new derivatives and their testing in the assembly of biosensors for drugs selection, in solar batteries, and in charge storage devices [ 48 , 49 , 50 , 51 , 52 ].…”

Section: Introductionmentioning

confidence: 99%

Voltammetric Sensor for Doxorubicin Determination Based on Self-Assembled DNA-Polyphenothiazine Composite

Malanina,

Kuzin,

Khadieva

et al. 2023

Nanomaterials

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A novel voltammetric sensor based on a self-assembled composite formed by native DNA and electropolymerized N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine has been developed and applied for sensitive determination of doxorubicin, an anthracycline drug applied for cancer therapy. For this purpose, a monomeric phenothiazine derivative has been deposited on the glassy carbon electrode from the 0.4 M H2SO4-acetone mixture (1:1 v/v) by multiple potential cycling. The DNA aliquot was either on the electrode modified with electropolymerized film or added to the reaction medium prior to electropolymerization. The DNA entrapment and its influence on the redox behavior of the underlying layer were studied by scanning electron microscopy and electrochemical impedance spectroscopy. The DNA–doxorubicin interactions affected the charge distribution in the surface layer and, hence, altered the redox equilibrium of the polyphenothiazine coating. The voltametric signal was successfully applied for the determination of doxorubicin in the concentration range from 10 pM to 0.2 mM (limit of detection 5 pM). The DNA sensor was tested on spiked artificial plasma samples and two commercial medications (recovery of 90–95%). After further testing on real clinical samples, the electrochemical DNA sensor developed can find application in monitoring drug release and screening new antitumor drugs able to intercalate DNA.

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3,7‐Bis(N‐methyl‐N‐phenylamino)phenothiazinium Salt: Improved Synthesis and Aggregation Behavior in Solution

Cited by 10 publications

References 55 publications

Arylamine Analogs of Methylene Blue: Substituent Effect on Aggregation Behavior and DNA Binding

Arylamine Analogs of Methylene Blue: Substituent Effect on Aggregation Behavior and DNA Binding

Amphiphilic Porphyrin Aggregates: A DFT Investigation

Voltammetric Sensor for Doxorubicin Determination Based on Self-Assembled DNA-Polyphenothiazine Composite

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