- Phenothiazine-based CaaX competitive inhibitors of human farnesyltransferase bearing a cysteine, methionine, serine or valine moiety as a new family of antitumoral compounds
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A new family of CaaX competitive inhibitors of human farnesyltransferase based on phenothiazine and carbazole skeleton bearing a l-cysteine, l-methionine, l-serine or l-valine moiety was designed, synthesized and biologically evaluated. Phenothiazine derivatives proved to be more active than carbazole-based compounds. Phenothiazine 1b with cysteine residue was the most promising inhibitor of human farnesyltransferase in the current study.
- Dumitriu, Gina-Mirabela,B?cu, Elena,Belei, Dalila,Rigo, Beno?t,Dubois, Jo?lle,Farce, Amaury,Ghinet, Alina
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- Ultrafast electrochromic windows based on redox-chromophore modified nanostructured semiconducting and conducting films
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Described is the construction of an ultrafast electrochromic window. One electrode of this window is based on a transparent nanostructured TiO2 (anatase) film (4.0 μm thick) supported on conducting glass (F-doped tin oxide, 10 Ω cm-2, 0.5 μm thick) and modified by chemisorption of a monolayer of the redox chromophore bis(2-phosphonoethyl)-4,4′-bipyridinium dichloride. The other electrode is based on a transparent nanostructured SnO2 film (3.0 μm thick) supported on conducting glass (F-doped tin oxide, 10 Ω cm-2, 0.5 μm thick) and modified by chemisorption of a monolayer of the redox chromophore [β-(10-phenothiazyl)propoxy]phosphonic acid. The electrolyte used is LiClO4 (0.2 mol dm-3) in γ-butyrolactone. The excellent performance of a 2.5 cm × 2.5 cm window over 10000 electrochromic test cycles-switching times (coloring and bleaching) of less than 250 ms, coloration efficiency of 270 cm2 C-1, steady-state currents (colored and bleached) of less than 6 μA cm-2, and memory of greater than 600 s (time required for low end transmittance to increase by 5%) - suggest a practical technology.
- Cummins, David,Boschloo, Gerrit,Ryan, Michael,Corr, David,Rao, S. Nagaraja,Fitzmaurice, Donald
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- Synthesis and analgesic evaluation of some 5-[β-(10-phenothiazinyl) ethyl]-1-(acyl)-1,2,3,4-tetrazoles
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A series of novel 5[β-(phenothiazinyl-10-yl)ethyl]-1-(acyl)-1,2,3,4- tetrazoles (3-14) have been synthesized via condensation of 5-[β- (phenothiazinyl-10-yl)ethyl]-1-2,3,4-tetrazole (2) with various acylating/sulphonating reagents. 5-[β-(phenothiazinyl-10
- Rajasekaran,Thampi
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- Phenothiazine electrophores immobilized on periodic mesoporous organosilicas by ion exchange
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Two different phenothiazines carrying quaternary ammonium groups in the side chain have been synthesized and fully characterized. These compounds were immobilized by ion exchange on the surface of a periodic mesoporous organosilica (PMO) and a neat silica SBA-15 material bearing sulphonate groups covalently bound to the pore surface. The resulting porous and electrochromophoric materials were studied by means of solid state CP-MAS NMR, IR, UV/Vis and fluorescence spectroscopy, nitrogen adsorption/desorption measurements and cyclic voltammetry. Independent of the nature of the support, the colour of these materials changes to pink by irradiation with light, indicating the formation of phenothiazine radical cations. These species, which turned out to be highly stable even in the presence of atmospheric oxygen, were characterized by EPR spectroscopy.
- Sch?fgen, Bj?rn,Khelwati, Hilla,Bechtel, Dominique F.,Decuyper, Annelies,Schüssler, Axel,Neuba, Adam,Pierik, Antonio J.,Ernst, Stefan,Müller, Thomas J. J.,Thiel, Werner R.
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- Electrical communication between glucose oxidase and electrodes mediated by phenothiazine-labeled poly(ethylene oxide) bonded to lysine residues on the enzyme surface
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A series of glucose oxidase (GOx) hybrids (GOx-phenothiazine-labeled poly(ethylene oxide) (PT-PEO)) capable of direct electrical communication with electrodes is synthesized by covalently modifying PT-PEO to lysine residues on the enzyme surface. The length of the PEO chain and the number of PT groups are systematically altered. After the PT-PEO modification, all the hybrids maintain more than 50% of enzyme activity relative to that of native GOx, although loss of the activity becomes greater with increasing PEO chain length. The catalytic current, icat, is observed at a potential more positive than 0.55 V after the addition of glucose, due to the intramolecular electron transfer (ET) from reduced forms of flavin adenine dinucletide (FADH2/FADH) to PT+ that are electrogenerated at the electrode. The icat value increases with the number of PT groups, indicating that most of the modified PT groups act as mediators. The magnitude of the icat increase depends on the PEO chain length and reveals a maximum for PT-PEO with the molecular weight of 3000. In contrast, the icat is almost constant for GOx-2-(10-phenothiazyl)propionic acid (PT-PA) hybrids with more than two PT groups synthesized by covalently modifying PT-PA to surface lysines, indicating that only a few key PT groups function as mediators. The maximum rate constant (130 s-1) for the ET from FADH2/FADH to PT+ is obtained for the GOx hybrid modified with five PT-PEO groups with the molecular weight of 3000.
- Ban, Kazumichi,Ueki, Takeshi,Tamada, Yoshinori,Saito, Takahiro,Imabayashi, Shin-ichiro,Watanabe, Masayoshi
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- Synthesis and bio-evaluation of phenothiazine derivatives as new anti-tuberculosis agents
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Abstract Two series of phenothiazine derivatives were designed and synthesized. All compounds were tested for anti-tuberculosis activities against Mycobacterium tuberculosis H37RV. In comparison with mother compound of chlorpromazine, compound 6e shows promising anti-tuberculosis activity and much less mammalian cell cytotoxicity, compound 6e merits to be further explored as new anti-tuberculosis agents.
- He, Chun-Xian,Meng, Hui,Zhang, Xiang,Cui, Hua-Qing,Yin, Da-Li
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- KOtBu-Catalyzed Michael Addition Reactions Under Mild and Solvent-Free Conditions
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Designed transition metal complexes predominantly catalyze Michael addition reactions. Inorganic and organic base-catalyzed Michael addition reactions have been reported. However, known base-catalyzed reactions suffer from the requirement of solvents, additives, high pressure and also side-reactions. Herein, we demonstrate a mild and environmentally friendly strategy of readily available KOtBu-catalyzed Michael addition reactions. This simple inorganic base efficiently catalyzes the Michael addition of underexplored acrylonitriles, esters and amides with (oxa-, aza-, and thia-) heteroatom nucleophiles. This catalytic process proceeds under solvent-free conditions and at room temperature. Notably, this protocol offers an easy operational procedure, broad substrate scope with excellent selectivity, reaction scalability and excellent TON (>9900). Preliminary mechanistic studies revealed that the reaction follows an ionic mechanism. Formal synthesis of promazine is demonstrated using this catalytic protocol.
- Thiyagarajan, Subramanian,Krishnakumar, Varadhan,Gunanathan, Chidambaram
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supporting information
p. 518 - 523
(2020/02/04)
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- Electrochemical primer extension for the detection of single nucleotide polymorphisms in the cardiomyopathy associated MYH7 gene
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We report the labelling of dideoxy nucleotides (ddNTPs) for use in electrochemical array based primer extension for the detection of single nucleotide polymorphisms (SNPs). The results confirm the extension of the immobilised primers for each of the four ddNTPs, representing a significant advance in achieving a cost-effective platform for screening of disease-specific SNPs.
- Debela,Thorimbert,Hasenknopf,O'Sullivan,Ortiz
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supporting information
p. 757 - 759
(2016/01/12)
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- Podands with 3,7,10-trisubstituted phenothiazine units: Synthesis and structural analysis
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The synthesis of 10H-phenothiazine dipodands exhibiting -CH2-OH or -CHO reactive groups at positions 3 and 7, suitable for macrocyclization reactions, as well as -CH2COOtBu or -CH2CH2CN groups at position 10, wh
- Rednic, Monica Irina,Szima, Szabolcs,Bogdan, Elena,H?dade, Niculina D.,Terec, Anamaria,Grosu, Ion
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p. 637 - 642
(2015/11/24)
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- Peptide chemistry applied to a new family of phenothiazine-containing inhibitors of human farnesyltransferase
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Novel phenothiazine derivatives bearing an amino acid residue were synthesized via peptide chemistry, and evaluated for their inhibitory potential on human farnesyltransferase. The phenothiazine unit proved to be an important bulky unit in the structure o
- Dumitriu, Gina-Mirabela,Ghinet, Alina,B?cu, Elena,Rigo, Beno?t,Dubois, Jo?lle,Farce, Amaury,Belei, Dalila
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p. 3180 - 3185
(2014/06/24)
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- New farnesyltransferase inhibitors in the phenothiazine series
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The biological screening of the chemical library of our Organic Chemistry Department, carried out on an automated fluorescence-based FTase assay, allowed us to discover that a phenothiazine derivative (1d) was an inhibitor of farnesyltransferase. Three new series of human farnesyltransferase inhibitors, based on a phenothiazine scaffold, were synthesized with protein farnesyltransferase inhibition potencies in the low micromolar range. Ester derivative 9d was the most active compound in these series. Four synthesized compounds were evaluated for their antiproliferative activity on a NCI-60 cancer cell line panel. The modest results obtained in this preliminary investigation showed that mixing the phenothiazine and the 1,2,3-triazole motif in the structure of a single compound can lead to new scaffolds in the field of farnesyltransferase inhibitors.
- Belei, Dalila,Dumea, Carmen,Samson, Alexandrina,Farce, Amaury,Dubois, Joelle,Bicu, Elena,Ghinet, Alina
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scheme or table
p. 4517 - 4522
(2012/08/07)
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- FLUORESCENCE MODULATORS
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The present invention relates to fluorescence lifetime modulators, conjugates comprising fluorescence lifetime modulators moieties and methods of making them. The present invention further relates to the use of the fluorescence lifetime modulators and conjugates comprising the fluorescence lifetime modulator moieties for measuring the activity and detection of enzymes and for the study of protein-protein and protein-ligand interactions.
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Page/Page column 125
(2012/09/10)
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- Redox active mesoporous hybrid materials by in situ syntheses with urea-linked triethoxysilylated phenothiazines
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Triethoxysilyl functionalized phenothiazinyl ureas were synthesized and immobilized by in situ synthesis into mesoporous hybrid materials. The designed precursor molecules influence the structure of the final materials and the intermolecular distance of the phe-nothiazines. XRD and N2 measurements indicate the presence ofhighly ordered two-dimensional hexag-onally structured functional materials, while the incorporation of the organic ompounds in the solid materials was proved by means of 13C and 29Si solid state NMR spectroscopy as well as by FT-IR spectroscopy. Upon oxidation with (NO)BF4 or SbCl5 stable pheno-thiazine radical cations were generated in the pores of the materials, which was detected by means of UV/Vis, emission, and EPR spectroscopies.
- Zhou, Zhou,Franz, Adam W.,Bay, Sarah,Sarkar, Biprajit,Seifert, Andreas,Yang, Piaoping,Wagener, Alex,Ernst, Stefan,Pagels, Markus,Mueller, Thomas J.J.,Thiel, Werner R.
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experimental part
p. 2001 - 2015
(2011/04/12)
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- Evidence of preferential π-stacking: A study of intermolecular and intramolecular charge transfer complexes
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Nine combinations of π-electron donors and acceptors were examined by UV-vis, fluorescence and 1H-NMR spectroscopy to identify π-stacked charge transfer complexes in macromolecular and supramolecular constructs. The high association constant of pyrene and naphthalene diimide suggests a preferentially π-stacking pair rationalized by frontier orbital congruence. The Royal Society of Chemistry 2010.
- Kumar, N. S. Saleesh,Gujrati, Maneesh D.,Wilson, James N.
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supporting information; scheme or table
p. 5464 - 5466
(2010/10/04)
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- Electrochromic compound
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A compound for use in electrochromic devices. The compound includes (1) β-(10-phenothiazyl)propoxy phosphonic acid; (2) β-(10-phenothiazyl)propyl-phosphonic acid; and (3) β-(10-phenothiazyl)propionate phosphonic acid.
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Page/Page column 8; 9; 11; 13-14; 15; 17-18
(2008/06/13)
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- Design, synthesis, and evaluation of efflux substrate-metal chelator conjugates as potential antimicrobial agents
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Maintaining a proper balance of metal concentrations is critical to the survival of bacteria. We have designed and synthesized a series of conjugates of metal chelators and efflux transporter substrates aimed at disrupting bacterial metal homeostasis to a
- Zhang, Yanling,Eric Ballard,Zheng, Shi-Long,Gao, Xingming,Ko, Ko-Chun,Yang, Hsiuchin,Brandt, Gary,Lou, Xinhui,Tai, Phang C.,Lu, Chung-Dar,Wang, Binghe
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p. 707 - 711
(2008/09/21)
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- Synthesis and stability of oligodeoxynucleotides containing C8-labeled 2'-deoxyadenosine: novel redox nucleobase probes for DNA-mediated charge-transfer studies.
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[reaction: see text] An efficient and convenient synthetic strategy to redox-labeled C8-derivatives of 2'-deoxyadenosine is described. The Pd(0) cross-coupling chemistry is amenable to both oxidative and reductive redox probes. The corresponding phosphoramidites of phenothiazine and anthraquinone nucleosides are amenable to automated DNA synthesis. The resulting labeled oligodeoxynucleotide strands form stable B-form duplexes with melting temperatures and CD spectra similar to those of the unlabeled analogues.
- Tierney,Grinstaff
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p. 3413 - 3416
(2007/10/03)
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A variety of triazoles and thiadiazoles linked to the N atom of the phenothiazine framework through a two carbon atom chain has been prepared from the corresponding thiosemicarbazides. The structure of the prepared five membered heterocycle depends on the choice of the appropriate cyclization agent (base or acid). Divers triazoles et thiadiazoles relies a l'atome d'azote de la phenothiazine par un segment carbone a deux atomes ont ete prepares a partir des thiosemicarbazides correspondants. La structure de l'heterocycle forme depend de la nature du traitement (basique ou acide) utilise lors de la cyclisation.
- Petrovanu, Magda,Bacu, Elena,Grandclaudon, Pierre,Couture, Axel
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p. 231 - 237
(2007/10/03)
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- Synthesis of phenothiazine derivatives as potential inhibitors of phospholipase C
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In order to study the structure-activity relationships of phenothiazine derivatives inhibiting phosphatidylinositol-specific phospholipase C (PI-PLC), the synthesis of some phenothiazine amide, amine and ester derivatives was performed mainly by reacting 10H-phenothiazine-10-propanoyl chloride with some amines and alcohols; the resulting amides were reduced with borane to yield the corresponding amines. Starting from 2-chloro and 2-trifuoromethyl-10H-phenothiazine-10-propanoyl chloride two amides were synthesized. The inhibiting activity on PI-PLC from human platelets is reported.
- Brufani,Cesta,Filocamo,Lappa,Marta,Pomponi,Meroni,Pagella
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p. 585 - 597
(2007/10/02)
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- On the Synthesis of 3-Amino-2,3-dihydro-1H-pyridophenothiazine 5,5-Dioxide and of 3-Amino-1,2-dihydro-3H-dibenzopyrido-1,4-thiazepine 7,7-Dioxide
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3-Amino-2,3-dihydro-1H-pyridophenothiazine 5,5-dioxide and 3-amino-1,2-dihydro-3H-dibenzopyrido-1,4-thiazepine 7,7-dioxide were synthesized from the corresponding 3-oxime acetates by reduction with the borane-tetrahydrofuran complex.Reduction was not successful in the case of 2,3-dihydro-1H-pyridophenothiazine-3-oxime acetate.
- Catsoulacos, P.,Pelecanou, M.,Camoutsis, Ch.
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p. 1437 - 1440
(2007/10/02)
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