Squaric monoamide monoester as a new class of reactive immunization hapten for catalytic antibodies

Xu, Yuanfu; Yamamoto, Noboru; Ruiz, Diana I.; Kubitz, Diane; Janda, Kim D.

doi:10.1016/j.bmcl.2005.06.052

Cited by 15 publications

(10 citation statements)

References 30 publications

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“…that can be used to isolate monoclonal antibodies with complimentary reactive residues in their combining sites. 70 The reactive immunogen 118 was designed to generate antibodies that bind the toxic insecticide paraoxon 119. Acid 118 was conjugated to the carrier protein BSA (bovine serum albumin) using standard amidation chemistry, and this conjugate was then used to inoculate mice (Scheme 19).…”

Section: Discussionmentioning

confidence: 99%

Squaramides: physical properties, synthesis and applications

2011

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Squaramides are remarkable four-membered ring systems derived from squaric acid that are able to form up to four hydrogen bonds. A high affinity for hydrogen bonding is driven through a concomitant increase in aromaticity of the ring. This hydrogen bonding and aromatic switching, in combination with structural rigidity, have been exploited in many of the applications of squaramides. Substituted squaramides can be accessed via modular synthesis under relatively mild or aqueous conditions, making them ideal units for bioconjugation and supramolecular chemistry. In this tutorial review the fundamental electronic and structural properties of squaramides are explored to rationalise the geometry, conformation, reactivity and biological activity.

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Section: Discussionmentioning

confidence: 99%

Squaramides: physical properties, synthesis and applications

2011

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“…By adding functionality to their hapten design to make it capable of binding an additional nucleophile once in the antibody pocket, they were able to increase the rate of antibody reactivity with their target substrate, but the observed reactivity was not catalytic hydrolysis in that the reactive site appeared to bind stoichiometrically and covalently to the paraoxon substrate. 31 A research team in France has worked since the late 1990s to develop catalytic antibodies specifically for the hydrolytic detoxification of agent VX. Their first targets were antibodies designed to stabilize the targeted transition state wherein a water molecule approaches the central phosphorus atom to create a pentacoordinate phosphorus-centered intermediate for the S N 2(P) reaction.…”

Section: Mutagenesis Of Oph Enzymesmentioning

confidence: 99%

Catalytic methods for the destruction of chemical warfare agents under ambient conditions

2008

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This tutorial review--which should particularly appeal to chemists, biochemists, and molecular biologists interested in catalysis, redox processes, and enzymology--summarizes the recent progress toward developing catalysts capable of destroying one or more of the classical chemical warfare agents under ambient conditions. Specifically, we explore the reactions of sulfur mustard, the G-series of organophosphorus nerve agents including sarin and soman, and the organophosphorus nerve agent, VX. Catalysts range from metal-centered oxidation catalysts to engineered catalytic antibodies.

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“…78 originally utilized to generate catalytic antibodies that hydrolyze paraoxon. 79 D. A sulfone transition state mimic for AHL hydrolysis as reported by Kapadnis et al . 80 …”

Section: Figmentioning

confidence: 90%

Chemical methods to interrogate bacterial quorum sensing pathways

2012

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Bacteria frequently manifest distinct phenotypes as a function of cell density in a phenomenon known as quorum sensing (QS). This intercellular signalling process is mediated by “chemical languages comprised of low-molecular weight signals, known as” autoinducers, and their cognate receptor proteins. As many of the phenotypes regulated by QS can have a significant impact on the success of pathogenic or mutualistic prokaryotic–eukaryotic interactions, there is considerable interest in methods to probe and modulate QS pathways with temporal and spatial control. Such methods would be valuable for both basic research in bacterial ecology and in practical medicinal, agricultural, and industrial applications. Toward this goal, considerable recent research has been focused on the development of chemical approaches to study bacterial QS pathways. In this Perspective, we provide an overview of the use of chemical probes and techniques in QS research. Specifically, we focus on: (1) combinatorial approaches for the discovery of small molecule QS modulators, (2) affinity chromatography for the isolation of QS receptors, (3) reactive and fluorescent probes for QS receptors, (4) antibodies as quorum “quenchers,” (5) abiotic polymeric “sinks” and “pools” for QS signals, and (6) the electrochemical sensing of QS signals. The application of such chemical methods can offer unique advantages for both elucidating and manipulating QS pathways in culture and under native conditions.

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Squaric monoamide monoester as a new class of reactive immunization hapten for catalytic antibodies

Cited by 15 publications

References 30 publications

Squaramides: physical properties, synthesis and applications

Squaramides: physical properties, synthesis and applications

Catalytic methods for the destruction of chemical warfare agents under ambient conditions

Chemical methods to interrogate bacterial quorum sensing pathways

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