Maleimides
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Maleimides
Maleimide is a chemical compound with the chemical formula, formula H2C2(CO)2NH (see diagram). This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group. Maleimides are also a ''class'' of derivatives of the parent maleimide where the N''H'' group is replaced with alkyl or aryl groups such as a methyl or phenyl, respectively. The substituent can also be a small molecule (such as biotin, a fluorescent dye, an oligosaccharide, or a nucleic acid), a reactive group, or a synthetic polymer such as polyethylene glycol. Human hemoglobin chemically modified with maleimide-polyethylene glycol is a blood substitute called MP4. Reactions Many analogues of maleimide are prepared by treating maleic anhydride with amines followed by dehydration. A defining feature of the reactivity of maleimides is their susceptibility to additions across the double bond either by Michael additions or via D ...
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Maleic Anhydride
Maleic anhydride is an organic compound with the formula . It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers. Structure and bonding Maleic anhydride is a planar molecule. By virtue of the acid anhydride group, the alkene is electrophilic. On account of its cycle of 4 π electrons in an array of 5 atoms with p orbitals, maleic anhydride was long thought to exhibit antiaromaticity. However, a thermochemical study concluded that only 8 kJ/mol of destabilization energy can be ascribed to this effect, making it weakly antiaromatic at best. Production Maleic anhydride is produced by vapor-phase oxidation of butane, ''n''-butane. The overall process converts the methyl groups to carboxylate and dehydrogenation, dehydrogenates the backbone. The selectivity of the process reflects the robustness of maleic anhydride, with its conjugated double-bond system. ...
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Farinomalein
Farinomalein is a natural maleimide with formula C10H13NO4 - was first isolated from the entomopathogenic fungus ''Isaria farinosa'' (''Paecilomyces farinosus'') - source H599 (Japan). Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic ''Phytophthora sojae''.Sastia Prama Putri, Hiroshi Kinoshita, Masayasu Kato and Takuya Nihira. ''Antimicrobial and antioomycete activities of the novel antibiotic farinomalein''. Poster Presentation 2P-2124, Annual Conference, The Society for Bioscience and Bioengineering, Japan, 28 October 2010. These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean. Synthesis A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(''H'')-furanone, has been reported. Firstly, the furanone is oxidized to 3-isopropylfuran-2,5-dione by Dess–Martin periodinane Dess–Martin periodina ...
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Pencolide
Pencolide is a maleimide isolate of ''Penicillium ''Penicillium'' () is a genus of Ascomycota, ascomycetous fungus, fungi that is part of the mycobiome of many species and is of major importance in the natural environment, in food spoilage, and in food and drug production. Some members of th ...'' and seaweed endophytic fungi. References Maleimides Carboxylic acids {{OrganicAcid-stub ...
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Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate
Succinimidyl 4-(''N''-maleimidomethyl)cyclohexane-1-carboxylate (SMCC) is a heterobifunctional amine-to-sulfhydryl crosslinker, which contains two reactive groups at opposite ends: N-hydroxysuccinimide-ester and maleimide, reactive with amines and thiols respectively. SMCC is often used in bioconjugation to link proteins with other functional entities (fluorescent dyes, tracers, nanoparticles, cytotoxic agents). For example, a targeted anticancer agent – trastuzumab emtansine ( antibody-drug conjugate containing an antibody trastuzumab Trastuzumab, sold under the brand name Herceptin among others, is a monoclonal antibody used to treat breast cancer and stomach cancer. It is specifically used for cancer that is HER2 receptor positive. It may be used by itself or together ... chemically linked to a highly potent drug DM-1) – is prepared using SMCC reagent. References {{Reflist Reagents for biochemistry Maleimides Succinimides ...
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Chemical Compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken or new bonds formed or both. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, usin ...
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Entomopathogenic Fungus
Entomopathogenic fungi are parasitic unicellular or multicellular microorganisms belonging to the kingdom of Fungi, that can infect and seriously disable or kill insects. Pathogenicity for insects is widely distributed in the kingdom of fungi and occur in six fungal phyla (Ascomycota, Oomycetes, Basidiomycota, Chytridiomycota, Zygomycota, and Microsporidia). It plays a vital ecological role in controlling insect populations by impacting 19 out of 30 known insect orders. Some fungal entomopathogens are opportunistic whereas some have evolved into highly specific pathogens of insects. Mode of infection Unlike many other insect pathogens (entomopathogenic viruses, nematodes, or bacteria), most entomopathogenic fungi do not require entry through ingestion or oral intake and instead directly attack the insect cuticle and penetrate the insect body through the exoskeleton. These fungi use a broad spectrum of virulence factors such as adhesins (to attach to insect cuticles), lytic enzym ...
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Streptomyces Showdoensis
''Streptomyces showdoensis'' is a bacterium species from the genus of ''Streptomyces'' which has been isolated from soil in Shōdoshima, Japan.Deutsche Sammlung von Mikroorganismen und Zellkulturen The Leibniz Institute DSMZ - German Collection of Microorganisms and Cell Cultures GmbH (German: ''Leibniz-Institut DSMZ-Deutsche Sammlung von Mikroorganismen und Zellkulturen GmbH''), located in Braunschweig, is a research infrastructure in the ...br>/ref> ''Streptomyces showdoensis'' produces terferol, actinomycin and showdomycin. See also * List of Streptomyces species References Further reading * * * * * External linksType strain of ''Streptomyces showdoensis'' at Bac''Dive'' - the Bacterial Diversity Metadatabase showdoensis Bacteria described in 1964 {{Streptomyces-stub ...
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Showdomycin
Showdomycin is a nucleoside antibiotic derived from ''Streptomyces showdoensis''. It is known for its antitumor and antimicrobial properties. Showdomycin was first isolated in the 1960s and has since been studied for its potential applications in cancer research and microbiology. Discovery and History Showdomycin was first discovered in 1964 by Japanese researchers during a screening of ''Streptomyces'' species for novel antibiotics. It was isolated from ''Streptomyces showdoensis'', a soil bacterium, and its structure was elucidated shortly thereafter. The compound gained attention for its unusual structure, which includes a maleimide ring fused to a ribose sugar, distinguishing it from other nucleoside antibiotics. Chemical Structure Showdomycin is a C-nucleoside, meaning the sugar is directly bonded to a carbon atom of the maleimide ring rather than a nitrogen atom, as seen in typical nucleosides. Its chemical formula is C9H11NO6, and its systematic name is 1-β-D-ribofur ...
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Cytotoxicity
Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of drugs, e.g alcohol, and some venom, e.g. from the puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles reclusa'') are toxic to cells. Cell physiology Treating cells with the cytotoxic compound can result in a variety of prognoses. The cells may undergo necrosis, in which they lose membrane integrity and die rapidly as a result of cell lysis. The cells can stop actively growing and dividing (a decrease in cell viability), or the cells can activate a genetic program of controlled cell death (apoptosis). Cells undergoing necrosis typically exhibit rapid swelling, lose membrane integrity, shut down metabolism, and release their contents into the environment. Cells that undergo rapid necrosis in vitro do not have sufficient ...
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N-hydroxysuccinimide
''N''-Hydroxysuccinimide (NHS) is an organic compound with the formula (CH2CO)2NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride. Activating reagent NHS is commonly found in organic chemistry or biochemistry where it is used as an activating reagent for carboxylic acids. Activated acids (carboxylates) can react with amines to form amides for example, whereas a normal carboxylic acid would just form a salt with an amine. Use A common way to synthesize an NHS-activated acid is to mix NHS with the desired carboxylic acid and a small amount of an organic base in an anhydrous solvent. A coupling reagent such as dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) is then added to form a highly reactive activated acid intermediate. NHS reacts to create a less labile activated acid. The group is us ...
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Thermosetting Polymer
In materials science, a thermosetting polymer, often called a thermoset, is a polymer that is obtained by irreversibly hardening (" curing") a soft solid or viscous liquid prepolymer (resin). Curing is induced by heat or suitable radiation and may be promoted by high pressure or mixing with a catalyst. Heat is not necessarily applied externally, and is often generated by the reaction of the resin with a curing agent (''catalyst'', '' hardener''). Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network. The starting material for making thermosets is usually malleable or liquid prior to curing, and is often designed to be molded into the final shape. It may also be used as an adhesive. Once hardened, a thermoset cannot be melted for reshaping, in contrast to thermoplastic polymers which are commonly produced and distributed in the form of pellets, and shaped into the final product form ...
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Crosslinking Reagent
In chemistry and biology, a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural polymers (such as proteins). In polymer chemistry "cross-linking" usually refers to the use of cross-links to promote a change in the polymers' physical properties. When "crosslinking" is used in the biological field, it refers to the use of a probe to link proteins together to check for protein–protein interactions, as well as other creative cross-linking methodologies. Although the term is used to refer to the "linking of polymer chains" for both sciences, the extent of crosslinking and specificities of the crosslinking agents vary greatly. Synthetic polymers : 260px, left, Chemical reactions associated with crosslinking of drying oils, the process that produces curing'' refers to the crosslinking of thermosetting">linoleum. Cros ...
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