Awesome and Easy Science Experiments about 3,4-Dibromo-1H-pyrrole-2,5-dione

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CO2/pH-responsive particles with built-in fluorescence read-out

A novel fluorescent monomer was synthesized to probe the state of CO2-responsive cross-linked polymeric particles. The fluorescent emission of this aminobromomaleimide-bearing monomer, being sensitive to protic environments, can provide information on the core hydrophilicity of the particles and therefore indicates the swollen state and size of the particles. The particles’ core, synthesized from DEAEMA (N,N-diethylaminoethyl methacrylate), is responsive to CO2 through protonation of the tertiary amines of DEAEMA. The response is reversible and the fluorescence emission can be recovered by simply bubbling nitrogen into the particle solution. Alternate purges of CO2 and N2 into the particles’ solution allow several ON/OFF fluorescence emission cycles and simultaneous particle swelling/shrinking cycles.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Structures of hydro-, chloro-, and bromo-substituted maleimides and 2,6-diaminopyridines, and of some of their 1:1 heterodimers

The crystal structures of a series of 3,4-diX-substituted maleimides and 3,5-diY-substituted-2,6-diaminopyridines (X, Y = H, Cl, Br) have been determined. Some of their hydrogen-bonded 1:1 heterodimers have also been synthesized and their crystal structures studied to investigate the influence of halogens on the crystal packing and to determine a possible role for halogen bonding. Single-crystal X-ray analysis of the crystals of the heterodimers revealed that the expected triple H-bonded structures were formed. This crystal engineering exercise has been partially successful, giving six mixed hydrogen- and (when possible) halogen-bonded compounds whose structures were found to be dependent on the nature and the position of the halogen substituents. The Royal Society of Chemistry 2011.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Synthesis of 2-hetaryl-3-(indol-1-yl)-and -(3-pyrrol-1-yl)maleimides and study of their conversions under the action of protic acids

A series of 3-(indol-1-yl)maleimides has been synthesized, substituted at position 2 by residues of amines or various nitrogenous heterocycles. The possibility of obtaining new polycondensed heterocyclic structures from them has been studied. Experimental investigations confirmed theoretical predictions made on the basis of results of quantum-chemical calculations.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Bacterial alkylquinolone signaling contributes to structuring microbial communities in the ocean

Background: Marine bacteria form complex relationships with eukaryotic hosts, from obligate symbioses to pathogenic interactions. These interactions can be tightly regulated by bioactive molecules, creating a complex system of chemical interactions through which these species chemically communicate thereby directly altering the host’s physiology and community composition. Quorum sensing (QS) signals were first described in a marine bacterium four decades ago, and since then, we have come to discover that QS mediates processes within the marine carbon cycle, affects the health of coral reef ecosystems, and shapes microbial diversity and bacteria-eukaryotic host relationships. Yet, only recently have alkylquinolone signals been recognized for their role in cell-to-cell communication and the orchestration of virulence in biomedically relevant pathogens. The alkylquinolone, 2-heptyl-4-quinolone (HHQ), was recently found to arrest cell growth without inducing cell mortality in selected phytoplankton species at nanomolar concentrations, suggesting QS molecules like HHQ can influence algal physiology, playing pivotal roles in structuring larger ecological frameworks. Results: To understand how natural communities of phytoplankton and bacteria respond to HHQ, field-based incubation experiments with ecologically relevant concentrations of HHQ were conducted over the course of a stimulated phytoplankton bloom. Bulk flow cytometry measurements indicated that, in general, exposure to HHQ caused nanoplankton and prokaryotic cell abundances to decrease. Amplicon sequencing revealed HHQ exposure altered the composition of particle-associated and free-living microbiota, favoring the relative expansion of both gamma- and alpha-proteobacteria, and a concurrent decrease in Bacteroidetes. Specifically, Pseudoalteromonas spp., known to produce HHQ, increased in relative abundance following HHQ exposure. A search of representative bacterial genomes from genera that increased in relative abundance when exposed to HHQ revealed that they all have the genetic potential to bind HHQ. Conclusions: This work demonstrates HHQ has the capacity to influence microbial community organization, suggesting alkylquinolones have functions beyond bacterial communication and are pivotal in driving microbial community structure and phytoplankton growth. Knowledge of how bacterial signals alter marine communities will serve to deepen our understanding of the impact these chemical interactions have on a global scale.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Reversible covalent linkage of functional molecules

The present invention relates to the use of a compound containing a moiety of formula (I) as a reagent for linking a compound of formula R1?H which comprises a first functional moiety of formula F1 to a second functional moiety of formula F2 wherein X, X?, Y, R1, F1 and F2 are as defined herein. The present invention also provides related processes and products. The present invention is useful for creating functional conjugate compounds, and specifically conjugates in which at least one of the constituent molecules carries a thiol group.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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CHEMICALLY-LOCKED BISPECIFIC ANTIBODIES

There is disclosed a process for forming chemically-locked bispecific or heterodimer antibodies, preferably in the IgG class, in high specificity and with high homogeneity. More specifically, there is disclosed a chemically-locked bispecific IgG class antibody having a linkage region joined together with bio-orthogonal click chemistry.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Enhancement of antibiotic activity against multidrug-resistant bacteria by the efflux pump inhibitor 3,4-dibromopyrrole-2,5-dione isolated from a pseudoalteromonas sp.

Members of the resistance nodulation cell division (RND) of efflux pumps play essential roles in multidrug resistance (MDR) in Gram-negative bacteria. Here, we describe the search for new small molecules from marine microbial extracts to block efflux and thus restore antibiotic susceptibility in MDR bacterial strains. We report the isolation of 3,4-dibromopyrrole-2,5-dione (1), an inhibitor of RND transporters, from Enterobacteriaceae and Pseudomonas aeruginosa, from the marine bacterium Pseudoalteromonas piscicida. 3,4-Dibromopyrrole-2,5-dione decreased the minimum inhibitory concentrations (MICs) of two fluoroquinolones, an aminoglycoside, a macrolide, a beta-lactam, tetracycline, and chloramphenicol between 2- and 16-fold in strains overexpressing three archetype RND transporters (AcrAB-TolC, MexAB-OprM, and MexXY-OprM). 3,4-Dibromopyrrole-2,5-dione also increased the intracellular accumulation of Hoechst 33342 in wild-type but not in transporter-deficient strains and prevented H33342 efflux (IC50 = 0.79g/mL or 3M), a hallmark of efflux pump inhibitor (EPI) functionality. A metabolomic survey of 36 Pseudoalteromonas isolates mapped the presence of primarily brominated metabolites only within the P. piscicida phylogenetic clade, where a majority of antibiotic activity was also observed, suggesting a link between halogenation and enhanced secondary metabolite biosynthetic potential. In sum, 3,4-dibromopyrrole-2,5-dione is a potent EPI and deserves further attention as an adjuvant to enhance the effectiveness of existing antibiotics.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Marine bacteria as source of antimicrobial compounds

The marine environment encompasses a huge biological diversity and can be considered as an underexplored location for prospecting bioactive molecules. In this review, the current state of art about antimicrobial molecules from marine bacteria has been summarized considering the main phylum and sources evolved in a marine environment. Considering the last two decades, we have found as most studied group of bacteria producers of substances with antimicrobial activity is the Firmicutes phylum, in particular strains of the Bacillus genus. The reason for that can be attributed to the difficult cultivation of typical Actinobacteria from a marine sediment, whose members are the major producers of antimicrobial substances in land environments. However, a reversed trend has been observed in recent years with an increasing number of reports settling on Actinobacteria. Great diversity of chemical structures have been identified, such as fijimicyns and lynamicyns from Actinomycetes and macrolactins produced by Bacillus.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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In vitro characterization and stability profiles of antibody?fluorophore conjugates derived from interchain cysteine cross-linking or lysine bioconjugation

Fluorescent labelling of monoclonal antibodies (mAbs) is classically performed by chemical bioconjugation methods. The most frequent labelling technique to generate antibody-fluorophore conjugates (AFCs) involves the bioconjugation onto the mAb lysines of a dye bearing an N-hydroxysuccinimide ester or an isothiocyanate group. However, discrepancies between labelling experiments or kits can be observed, related to reproducibility issues, alteration of antigen binding, or mAb properties. The lack of information on labelling kits and the incomplete characterization of the obtained labelled mAbs largely contribute to these issues. In this work, we generated eight AFCs through either lysine or interchain cysteine cross-linking bioconjugation of green-emitting fluorophores (fluorescein or BODIPY) onto either trastuzumab or rituximab. This strategy allowed us to study the influence of fluorophore solubility, bioconjugation technology, and antibody nature on two known labelling procedures. The structures of these AFCs were thoroughly analyzed by mass spectroscopy, and their antigen binding properties were studied. We then compared these AFCs in vitro by studying their respective spectral properties and stabilities. The shelf stability profiles and sensibility to pH variation of these AFCs prove to be dye-, antibody- and labelling-technology-dependent. Fluorescence emission in AFCs was higher when lysine labelling was used, but cross-linked AFCs were revealed to be more stable. This must be taken into account for the design of any biological study involving antibody labelling.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Mechanochemical Fluorescence Switching in Polymers Containing Dithiomaleimide Moieties

Polymers that display useful mechanochemical responses, such as changes of their fluorescence characteristics, are attracting great interest. Here, we introduce the fluorescent dithiomaleimide (DTM) motif as a mechanofluorophore and report the mechanoresponse of two polymer types containing this motif. Poly(methyl acrylate) (PMA) and poly(?-caprolactone)s (PCL) featuring one DTM moiety in the center of each chain (PMA-DTM and PCL-DTM) were synthesized by controlled radical and coordination-insertion ring-opening polymerizations using bifunctional DTM-containing initiators. Upon ultrasonic treatment of PMA-DTM or PCL-DTM of sufficiently high initial molecular weight, both the molecular weight and the fluorescence intensity decreased with similar kinetics, while no significant fluorescence changes were observed for DTM-free reference polymers. The results show that the DTM motif can serve as a mechanophore that displays a mechanically induced fluorescence turn-off.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem