Structure-activity Relationship of Phenothiazines for Inhibition of Protein Kinase C and Reversal of Multidrug Resistance

Studies on structure-activity relationship of phenothiazines (PTZs) forinhibition of protein kinase C (PKC) and reversal of multidrug resistance (MDR) has been made invitro. The results showed that the order of potency of reversal effect of PTZs on MDR is as follows:2-COC_3 H_7 > 2-CF_3 > 2-COCH_3 > H. The type of piperazinyl substitution also significantlyaffected potency against MDR. The results show the order: CH_3 > COOC_2 H_5 > C_2 H_4 OH. Inaddition, PKC plays a marked role in diverse cellular process including MDR. Some derivatives of PTZwas tested for inhibition of PKC, of which PTZ11 showed the highest inhibitory effect of MDR andPKC, implying a potential reversal agent of MDR for tumor therapy in the future. We also tried toexplore the possible binding model of PTZs to PKC. Our molecular-modeling study preliminarilysuggests how these PTZs bind to PKC and provides a structural basis for the design of high affinityPKC-modulator. The infor-mation may be used in the rational design of more effective drugs.

Flame-retarding battery cathode materials based on reversible multi-electron redox chemistry of phenothiazine-based polymer

Polymeric organic battery materials are promising alternatives to the transition-metal-based ones owing to their enriched chemistries. However, the flammability of organic compounds brings in serious concern on battery safety. In addition to use flame-retarding electrolyte/electrolyte additives or battery separators,flame retardancy can readily be achieved through the integration of flame-retarding unit into the polymer backbone, imparting the flame retardancy permanently. The as-designed polymer based on phenothiazine shows significantly shortened self-extinguished time without deteriorating its intrinsic thermodynamic and electrochemical properties. Moreover, two electron per phenothiazine molecule is realized for the first time in a highly reversible manner with discharge voltages of 3.52 V and 4.16 V versus Li+/Li and an average capacity of ca. 120 mAh g-1 at a current rate of 2 C. The origin of the reversibility is investigated through density functional theory(DFT) calculations. These findings address the importance of molecular design for safer and more stable organic materials for batteries.

Fluorescence Quenching of Anthracene by N,N-Diethylaniline and Phenothiazine in Triton X-100/n-C_(10)H_(21) OH/H_2O Microemulsion

The photo-induced electron transfer reactions of anthracene with N,N -diethylaniline(DEA) and phenothiazine(PTZ) occur in the membrane phase of a Triton X-100/ n -C 10 H 21 OH(1-decanol)/H 2O microemulsion. DEA and PTZ exist in the membrane phase of the microemulsion. Anthracene exists in the oil continuous phase of the W/O microemulsion and in the oil core and membrane phase of the O/W microemulsion.

ESR Studies on N-Alkylphenothiazine Radical Cation Salts

he stable radical cation salts of phenothiazine and N-alkyl-phenothiazine(alkyl =methyl , ethyl , isohutyl , isopentyl and benzyl) hexachloroantimonate ,per-chlorate , and iodide were prepared by means of one-electron oxidation with 2 ,2 , 6 ,6-tetramethyl- 4-acetoxypiperidine oxoammonium hexachloroantimonate , perchloricacid, hydrogen peroxide, and molecular iodine, respectively. The radical cationswere characterized using ESR spectroscopy. Conformational analysis based on theESR parameters suggests that the radical cations adopt a planar configuration withthe nitrogen radical as the center.

Phenothiazine vs 5HT3 Antagonist Prophylactic Regimens to Prevent Post‐Anesthesia Care Unit Rescue Antiemetic: An Observational Study

Purpose: Our practitioners are asked to consider a patient’s postoperative nausea and vomiting (PONV) risk profile when developing their prophylactic antiemetic strategy. There is wide variation in employed strategies, and we have yet to determine the most effective PONV prophylactic regimen. The objective of this study is to compare prophylactic antiemetic regimens containing: phenothiazines to 5HT3 antagonists for effectiveness at reducing the incidence of Post‐Anesthesia Care Unit (PACU) rescue antiemetic administration. Methods: This is an observational study of 4392 nonsmoking, women who underwent general anesthesia for breast surgery from 1/1/2009 through 6/30/2012. Previous history of PONV or motion sickness (HxPONV/MS) and the use of PACU opioids were recorded. Prophylactic antiemetic therapy was left to the discretion of the anesthesia care team. We compared phenothiazines and 5HT3 antagonists alone and with a glucocorticoid to determine the most effective treatment regimen in our practice for the prevention of the administration of PACU rescue antiemetics. Results: Patients who received a phenothiazine regimen compared to a 5HT3 antagonist regimen were less likely to have an antiemetic administered in the PACU (p = 0.0100) and this significant difference in rates holds in a logistic regression model adjusted for HxPONV/MS and PACU Opioid use (p = 0.0103). Conclusions: Based on our findings our clinicians are encouraged to administer a combination of a phenothiazine and a glucocorticoid in female, nonsmoking surgical breast patients for the prevention of PACU rescue antiemetic administration.

SYNTHESIS AND CHARACTERIZATION OF PHENOTHIAZINE-BASED PPV-TYPE COPOLYMERS CONTAINING FLUORENE AND THIOPHENE MOIETIES

Copolymers of fluorene-co-phenothiazine （ P1） and th iophene-co-phenothiazine （ P2 ） were prepared respectively by Wittig reaction. The synthesis, photo-physical and electroluminescent properties of the resulting polymers were analyzed by FT-IR, GPC, IH-NMR, UV-Vis, Photoluminescence （PL）, Electroluminescence （EL） and Cyclic Voltammetry （CV）. Their single layer devices with configuration of lTO/polymers/Ca/Al were studied. GPC results revealed the weight-average molecular weight （Mw） was 3.0×10^3 and 5.4×10^3, respectively. The device with a single layer structure of ITO/P1/Ca/Al emits green light with the maximum peak at 552nm. However, the device with a single layer structure of ITO/P2/Ca/Al emit red light with the maximum peak at 616nm.

Absorption Complex between Porphyrin and Phenothiazine in Reverse Micelles

The interaction between amphiphilic porphyrin and phenothiazine in AOT/isooctane/water reverse micelle was investigated by UV-Vis spectra. A new absorption complex between the two species is formed in such circumstances, which is ascribed to the enrichment of the components by the reverse micelle. The fluorescence quenching of CHTTP by PTH becomes more efficient after the formation of the absorption complex.

One—and Two—photon Excited Fluorescence of Zinc（Ⅱ）,Cadmium（Ⅱ）Complexes Containing Phenothiazine Ligand

A new ligand, 10ethylphenothiazinyl 3 yl methylene thiosemicarbazon (HL) and its complexes ML2 (M=Zn2+, Cd2+), which exhibit intensive two-photon excited (TPE) fluorescence at 800 nm laser pulses in femtosecond regime, were synthesized and characterized. The measured power dependence of the fluorescence signals provided direct evidence for TPE. All of them exhibited a large two-photon absorptive cross section and, more importantly from the application point of view, high photochemical/photothermal stability.

Inclusion Complexation of β-CD with Phenothiazine and N-Alkylphenothiazine Derivatives

Inclusion of Acyclodextrin (ACD) with phenothiazine 1 and Nalkylpheno-thiazine derivatives (alkyl = ethyl 2, isobutyl 3 and isopentyl 4) in aqueous solution was studied by means of UV-vis spectroscopy. The association constant Ka values for the inclusion of β-CD with 1, 2, 3 and 4 were determined to be 188, 214, 129 and 80 L/mol, respectively. It indicates that the stability of the inclusion complexes is dependent on the structure and the volume of the substituents in the guest compounds.

Hydrogen Bonding Effects on the Photophysical Properties of 2,3-dihydro-3-keto- 1H-pyrido[3,2,1-kl] phenothiazine

Time-dependent density functional theory （TDDFT） and femtosecond transient absorption spectroscopy were used to investigate the photophysical properties of 2,3-dihydro-3-keto-lH- pyrido[3,2,1-kl]phenothiazine （PTZ4） and 3-keto-lH-pyrido[3,2,1-kl]phenothiazine （PTZ5）. The calculated results obtained from TDDFT suggest that the red-shifts of the absorption spectra of these two fluorophores in methanol are due to the formation of hydrogen-bonded complexes at the ground state. Four conformers of PTZ4 were obtained by TDDFT. The two fluorescence peaks of PTZ4 in tetrahydrofuran （THF） came from the ICT states of the four conformers. The fluorescence of PTZ4 in THF showed a dependence on the excitation wavelength because of butterfly bending. The excited state dynamics of PTZ4 in THF and methanol were obtained by transient absorption spectroscopy. The lifetime of the excited PTZ4 in methanol was 53.8 ps, and its relaxation from the LE state to the ICT state was completed within several picoseconds. The short lifetime of excited PTZ4 in methanol was due to the formation of out-of-plane model hydrogen bonds between PTZ4 and methanol at the excited state.

Synthesis, Crystal Structure and Electrochemical Properties of a Novel Phenothiazine Derivative

A new compound 1,1?-bis(3-pyridyl)-propylene(3,7-diformyl-N-ethylpheno- thiazinyl)ketone (C30H23N3O2S, Mr = 489.4) has been synthesized, and its crystal structure was determined by single-crystal X-ray diffraction method. The crystal is of orthorhombic, space group Ima2 with a = 27.491(5), b = 11.942(2), c = 7.389(2) ?, V = 2425.8(7) ?3, Z = 8, Dc = 1.340 g/cm3, μ = 0.167 mm-1, F(000) = 1024, the final R = 0.0363 and wR = 0.0869 for 2054 unique reflections with Rint = 0.0254. The structural determination shows that the molecule assumes a butterfly configuration with nearly planar wings. In addition, the electrochemical study indicates that there is a high electronic delocalization in the molecule.

CATALYTIC REDUCTION OF HEMOGLOBIN AT PHENOTHIAZINE COATED SILVER ELECTRODE

Phenothiazine-coated silver electrode prepared by a simple reaction of phenothiazine with the metal is very stable and can make the reduction of hemoglobin possible.

Theoretical Study on Thermodynamic Properties and Hydrophilicity of Polychorinated Phenothiazines (PCPTZs)

The thermodynamic properties of 135 polychlorinated phenothiazines （PCPTZs） in the standard state are calculated using a combination of quantum mechanical computations performed with the Gaussian 03 program at the B3LYP/6-311G^＊＊ level, and their octanol-water partition coefficients （logKow） are calculated based on group contributions. The chlorine substitution pattern strongly influenced the thermodynamic properties and hydrophilicity of the compounds. The thermodynamic properties of congeners also depend on the chlorine substitution pattern. The effect of chlorine substitution pattern is quantitatively studied by considering the mmaber and position of Cl atom substitution （Npcs）. The results show that the Npcs model may be used to predict the thermodynamic properties and hydrophilicity for all 135 PCPTZ congeners.

Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine)activated NIR luminescence for lysosome imaging

Macrocycle confinement induced guest near-infrared(NIR)luminescence was research hotspot currently.Here in,we reported a cucurbit[7]uril(CB[7])confined 3,7-bis((E)-2-(pyridin-4-yl)vinyl)-10-Hphenothiazine bridged bis(4-(4-bromophenyl)pyridine)(G),which not only boosted its NIR luminescence but also realized detection of HClO/ClO^(-)in living cells and lysosome imaging.Fluorescence spectroscopy experiments were performed to calculate the detection ability of probe G to HClO/ClO^(-)up to 147 nmol/L.As compared with G,supramolecular probe G■CB[7]formed after encapsulated by CB[7],the detection ability towards HClO/ClO^(-)was improved to 24 nmol/L which was ascribe to the macrocycle CB[7]confinement increasing the fluorescence intensity to 103 folds.Accompanying the excitation wavelength changing,the fluorescence red-shifted to 820 nm when excited by 570 nm light,which was used to NIR lysosome imaging.Meanwhile,the supramolecular assembly G■CB[7]was also successfully used to highly sense to exogenous HClO/ClO^(-)in RAW 264.7 cells and live animal.

Efficient photo-induced RTP materials based on phenothiazine and polycyclic aromatic hydrocarbons:Tunable emission color and thermal stimulus response

The development of photo-responsive room temperature phosphorescence(RTP)materials has attracted more and more attention for their broad application pro-spects.Until now,it is still difficult to obtain the related ma-terials with both high efficiency and long lifetime.And the lacking of emission in blue and red regions also largely re-stricts their further applications.In this work,we reported a new strategy to maintain both high efficiency and long lifetime in RTP luminogens through the integration of phenothiazine to facilitate n-π*transition and polycyclic aromatic hydro-carbons(PAHs)dominated byπ-π*transition.When they were doped into polymer matrix,full color photo-induced RTP materials were obtained for the changedπ-conjugation of PAHs.Among them,PTri@PVP showed the best RTP per-formance with phosphorescence efficiency of 20.73%and lifetime up to 819 ms.Specifically,after turning off the ul-traviolet-visible(UV)irradiation upon this system,time-de-pendent phosphorescence afterglow from green to blue was exhibited,which was found to originate from two distinct molecular conformations and could be further regulated by thermal stimulus.Accordingly,multiple anti-counterfeiting applications,including screen printing,multi-color patterns and multi-dimensional information encryption,were suc-cessfully demonstrated.

Photoinduced Room-Temperature Phosphorescence of Triphenylamine-Phenothiazine Derivative-Doped Polymers

Photo-responsive room-temperature phosphorescent(RTP)materials have garnered significant interest due to the advantages of rapid response,spatiotemporal control,and contactless precision manipulation.However,the development of such materials remains in its infancy,underscoring the importance of exploiting novel and efficient light-responsive RTP molecules.In this work,three phenothiazine derivatives of TPA-PTZ,TPA-2PTZ,and TPA-3PTZ were successfully synthesized via the Buchwald-Hartwig C—N coupling reaction.By embedding these molecules as RTP guests into polymethyl methacrylate(PMMA)matrix,photo-induced RTP properties were realized.Upon sustained UV irradiation,there was an enhancement of 19 times in the quantum yield to reach a value of 5.68%.Remarkably,these materials exhibit superior alongside robust light and thermal stability,maintaining high phosphorescence intensity even after prolonged UV exposure(irradiation for>200 s by a 365 nm UV lamp with the power of 500μW·cm-2)or at higher temperature up to 75℃.The outstanding properties of these photo-induced RTP materials make them promising candidates for applications in information encryption,anti-counterfeiting,and advanced optical materials.

Electrochemical C-H/N-H cross-coupling of 2-phenylindolizines with phenothiazines to synthesize novel N-aryl phenothiazine derivatives

A facile and elegant method for synthesis of novel N-aryl phenothiazine derivatives from 2-phenylindolizines and phenothiazines through direct electrochemical oxidation has been developed.This approach was performed smoothly at room temperature without external oxidant and catalyst.Cyclic voltammetry and in situ FTIR techniques were applied to analyze the cross-coupling process of phenothiazines and 2-phenylindolizines,which helped to select the appropriate reaction potential.Under the optimized conditions,a broad range of substrates were well tolerated,affording the desired products in moderate to excellent isolated yields(up to 91%)with high regioselectivity.Meanwhile,a plausible mechanism involving a radical pathway has been proposed.

Recent advances in phenothiazine-based dyes for dye-sensitized solar cells

Dye-sensitized solar cells（DSSCs） have attracted significant attention as alternatives to conventional silicon-based solar cells owing to their low-cost production,facile fabrication,excellent stability and high power conversion efficiency（PCE）.The dye molecule is one of the key components in DSSCs since it significant influence on the PCE,charge separation,light-harvesting,as well as the device stability.Among various dyes,easily tunable phenothiazine-based dyes hold a large proportion and achieve impressive photovoltaic performances.This class of dyes not only has superiorly non-planar butterfly structure but also possesses excellent electron donating ability and large π conjugated system.This review summarized recent developments in the phenothiazine dyes,including small molecule phenothiazine dyes,polymer phenothiazine dyes and phenothiazine dyes for co-sensitization,especially focused on the developments and design concepts of small molecule phenothiazine dyes,as well as the correlation between molecular structures and the photovoltaic performances.

Effect of chenodeoxycholic acid (CDCA) additive on phenothiazine dyes sensitized photovoltaic performance

The effects of chenodeoxycholic acid (CDCA) in a dye solution as a co-adsorbent on the photovoltaic performance of dye-sensitized solar cells (DSSCs) based on two organic dyes containing phenothiazine and triarylamine segments (P1 and P2) were investigated.It was found that the coadsorption of CDCA can hinder the formation of dye aggregates and improve electron injection yield and thus Jsc.This has also led to a rise in photovoltage,which is attributed to the decrease of charge recombination.The DSSC based on dye P2 showed better photovoltaic performance than P1:a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 89.5%,a short-circuit photocurrent density (Jsc) of 9.57 mA/cm2,an open-circuit photovoltage (Voc) of 697 mV,and a fill factor (FF) of 0.66,corresponding to an overall conversion efficiency of 4.42% under the standard global AM 1.5 solar light condition.The overall conversion efficiency was further improved to 5.31% (Jsc=10.36 mA/cm2,Voc=0.730 V,FF=0.70) upon addition of 10 mM CDCA to the dye solution for TiO2 sensitization.Electrochemical impedance data indicate that the electron lifetime was improved by coadsorption of CDCA,accounting for the significant improvement of Voc.These results suggest that interfacial engineering of the organic dye-sensitized TiO2 electrodes is important for highly efficient photovoltaic performance of the solar cell.