Design, synthesis, and in vitro evaluation of an activity-based protein profiling (ABPP) probe targeting agmatine deiminases

Thomson, Andrew J.; O’Connor, Sean Timothy Francis; Knuckley, Bryan; Causey, Corey P.

doi:10.1016/j.bmc.2014.07.028

Cited by 8 publications

(9 citation statements)

References 23 publications

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“…Recently, two novel haloacetamidine-based AgD inactivators (ABCA and ABFA) have been developed and are the most potent AgD inhibitors described to date [ 7 , 8 , 21 , 22 ]. Since L. monocytogenes AgD utilizes a conserved active site cysteine, we evaluated the effectiveness of these mechanism-based inactivators on this enzyme.…”

Section: Discussionmentioning

confidence: 99%

Mechanistic studies of the agmatine deiminase from Listeria monocytogenes

Soares

Knuckley

2016

Biochemical Journal

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Section: Discussionmentioning

confidence: 99%

Mechanistic studies of the agmatine deiminase from Listeria monocytogenes

Soares

Knuckley

2016

Biochemical Journal

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“…The compound 4,7-di(thien-2-yl)-2,1,3-benzothiadiazole-5,6-dicarboxylic anhydride (8) was synthesised by intramolecular ring closure of 7, in the presence of acetic anhydride and anhydrous xylene at 130 • C, as a red solid in an excellent yield of 97% [52]. 3,7-dimethyloctyl bromide (9) was synthesised from the reaction of commercially available 3,7-dimethyl-1-octanol with triphenylphosphine (Ph 3 P)/NBS in dichloromethane as a colourless oil in 73% yield [53]. Then, 9 was reacted with potassium phthalimide in anhydrous DMF to give N-(3,7-dimethyloctyl) phthalimide (10) as colourless oil in an excellent yield of 91% [54].…”

Section: Synthesis Of Monomers and Polymersmentioning

confidence: 99%

“…The substance was stirred in petroleum ether for 1h at RT, filtered and the filtrate evaporated. The product was purified by chromatography with petroleum ether to yield 9 as colourless oil (23.00 g, 59 mmol, 73% yield)[53] 1. H NMR (CDCl 3 , δ): 3.55-3.37 (m, 2H), 1.96-1.83 (m, 1H), 1.77-1.61 (m, 2H), 1.60-1.49 (m, 1H), 1.41-1.24 (m, 3H), 1.22-1.11 (m, 3H), 0.82-0.94 (m, 9H) 13.…”

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confidence: 99%

Influence of Fluorine Substitution on the Optical, Thermal, Electrochemical and Structural Properties of Carbazole-Benzothiadiazole Dicarboxylic Imide Alternate Copolymers

Murad¹,

Iraqi

Aziz

et al. 2020

Polymers

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In this work four novel donor-acceptor copolymers, PCDTBTDI-DMO, PCDTBTDI-8, P2F-CDTBTDI-DMO and P2F-CDTBTDI-8, were designed and synthesised via Suzuki polymerisation. The first two copolymers consist of 2,7-carbazole flanked by thienyl moieties as the electron donor unit and benzothiadiazole dicarboxylic imide (BTDI) as electron acceptor units. In the structures of P2F-CDTBTDI-DMO and P2F-CDTBTDI-8 copolymers, two fluorine atoms were incorporated at 3,6-positions of 2,7-carbazole to investigate the impact of fluorine upon the optoelectronic, structural and thermal properties of the resulting polymers. P2F-CDTBTDI-8 possesses the highest number average molecular weight (Mn = 24,200 g mol−1) among all the polymers synthesised. PCDTBTDI-DMO and PCDTBTDI-8 show identical optical band gaps of 1.76 eV. However, the optical band gaps of fluorinated copolymers are slightly higher than non-fluorinated counterparts. All polymers have deep-lying highest occupied molecular orbital (HOMO) levels. Changing the alkyl chain substituents on BTDI moieties from linear n-octyl to branched 3,7-dimethyloctyl groups as well as substituting the two hydrogen atoms at 3,6-positions of carbazole unit by fluorine atoms has negligible impact on the HOMO levels of the polymers. Similarly, the lowest unoccupied molecular orbital (LUMO) energy levels are almost comparable for all polymers. Thermogravimetric analysis (TGA) has shown that all polymers have good thermal stability and also confirmed that the fluorinated copolymers have higher thermal stability relative to those non-fluorinated analogues. Powder X-ray diffraction (XRD) studies proved that all polymers have an amorphous nature in the solid state.

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“…The organic extracts were combined, and then washed with KOH and deionized water. The organic phase was dried over MgSO 4 , and the solvent was evaporated to obtain the product, which was purified via chromatography with DCM to yield 10 as colourless oil (5.29 g, 18 mmol, 91% yield) [31]. 1 Synthesis of 3,7-dimethyl-1-octanamine (11): 10 (6.03 g, 20.98 mmol), hydrazine hydrate (4.0 mL, 65.0 mmol, 51%), and methanol (100 mL) were combined in a flask.…”

Section: Monomers and Polymers Synthesismentioning

confidence: 99%

“…Moreover, 3,7-dimethyloctyl bromide (9) was synthesized from the reaction of commercially available 3,7-dimethyl-1-octanol with triphenylphosphine (Ph 3 P)/NBS in dichloromethane to yield 9 as a colourless oil in 73% yield [30]. Then, 9 was reacted with potassium phthalimide in anhydrous DMF to give N-(3,7-dimethyloctyl)phthalimide (10) as a colourless oil in an excellent yield of 91% [31]. 3,7-dimethyl-1-octanamine (11) was obtained by Gabriel synthesis from the reaction of 10 with hydrazine hydrate (NH 2 NH 2 ) in methanol as brown oil in 86% yield [44].…”

Section: Monomers and Polymers Synthesismentioning

confidence: 99%

Fabrication of Alternating Copolymers Based on Cyclopentadithiophene-Benzothiadiazole Dicarboxylic Imide with Reduced Optical Band Gap: Synthesis, Optical, Electrochemical, Thermal, and Structural Properties

et al. 2020

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A series of alternating copolymers containing cyclopentadithiophene (CPDT) flanked by thienyl moieties as electron-donor units and benzothiadiazole dicarboxylic imide (BTDI) as electron-acceptor units were designed and synthesized for solar cell applications. Different solubilizing side chains, including 2-ethylhexyl chains and n-octyl chains were attached to CPDT units, whereas 3,7-dimethyloctyl chains and n-octyl chains were anchored to the BTDI moieties. The impact of these substituents on the solubilities, molecular weights, optical and electrochemical properties, and thermal and structural properties of the resulting polymers was investigated. PCPDTDTBTDI-EH, DMO was synthesized via Suzuki polymerization, whereas PCPDTDTBTDI-8, DMO, and PCPDTDTBTDI-EH, 8 were prepared through direct arylation polymerization. PCPDTDTBTDI-8, DMO has the highest number average molecular weight (Mn = 17,400 g mol−1) among all polymers prepared. The PCPDTDTBTDI-8, DMO and PCPDTDTBTDI-8, 8 which have n-octyl substituents on their CPDT units have comparable optical band gaps (Eg ~ 1.3 eV), which are around 0.1 eV lower than PCPDTDTBTDI-EH, DMO analogues that have 2-ethylhexyl substituents on their CPDT units. The polymers have their HOMO levels between −5.10 and −5.22 eV with PCPDTDTBTDI-EH, DMO having the deepest highest occupied molecular orbital (HOMO) energy level. The lowest unoccupied molecular orbital (LUMO) levels of the polymers are between −3.4 and −3.5 eV. All polymers exhibit good thermal stability with decomposition temperatures surpassing 350 °C. Powder X-ray diffraction (XRD) studies have shown that all polymers have the amorphous nature in solid state.

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Design, synthesis, and in vitro evaluation of an activity-based protein profiling (ABPP) probe targeting agmatine deiminases

Cited by 8 publications

References 23 publications

Mechanistic studies of the agmatine deiminase from Listeria monocytogenes

Mechanistic studies of the agmatine deiminase from Listeria monocytogenes

Influence of Fluorine Substitution on the Optical, Thermal, Electrochemical and Structural Properties of Carbazole-Benzothiadiazole Dicarboxylic Imide Alternate Copolymers

Fabrication of Alternating Copolymers Based on Cyclopentadithiophene-Benzothiadiazole Dicarboxylic Imide with Reduced Optical Band Gap: Synthesis, Optical, Electrochemical, Thermal, and Structural Properties

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