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Nuclear Medicine and Biology 2021Hydrogen cyanide (HCN) is a versatile synthon for generating carbon‑carbon and carbon-heteroatom bonds. Unlike other one-carbon synthons (i.e., CO, CO), HCN can... (Review)
Review
Hydrogen cyanide (HCN) is a versatile synthon for generating carbon‑carbon and carbon-heteroatom bonds. Unlike other one-carbon synthons (i.e., CO, CO), HCN can function as a nucleophile (as in potassium cyanide, KCN) and an electrophile (as in cyanogen bromide, (CN)Br). The incorporation of the CN motif into organic molecules generates nitriles, hydantoins and (thio)cyanates, which can be converted to carboxylic acids, aldehydes, amides and amines. Such versatile chemistry is particularly attractive in PET radiochemistry where diverse bioactive small molecules incorporating carbon-11 in different positions need to be produced. The first examples of making [C]HCN for radiolabeling date back to the 1960s. During the ensuing decades, [C]cyanide labeling was popular for producing biologically important molecules including C-labeled α-amino acids, sugars and neurotransmitters. [C]cyanation is now reemerging in many PET centers due to its versatility for making novel tracers. Here, we summarize the chemistry of [C]HCN, review the methods to make [C]HCN past and present, describe methods for labeling different types of molecules with [C]HCN, and provide an overview of the reactions available to convert nitriles into other functional groups. Finally, we discuss some of the challenges and opportunities in [C]HCN labeling such as developing more robust methods to produce [C]HCN and developing rapid and selective methods to convert nitriles into other functional groups in complex molecules.
Topics: Positron-Emission Tomography
PubMed: 34624831
DOI: 10.1016/j.nucmedbio.2021.09.002 -
Organic & Biomolecular Chemistry Apr 2023A practical, one-pot approach to 3-anilino-4-(het)arylmaleimides by simple heating of aqueous DMSO solution of 2'-nitrochalcones with potassium cyanide in the presence...
A practical, one-pot approach to 3-anilino-4-(het)arylmaleimides by simple heating of aqueous DMSO solution of 2'-nitrochalcones with potassium cyanide in the presence of formic acid has been developed. This new reaction provides effective access to a variety of β-substituted α-aminomaleimides which have recently become a subject of growing interest as small, easily modified and environmentally responsive fluorescent probes.
PubMed: 36945887
DOI: 10.1039/d3ob00197k -
Brain and Nerve = Shinkei Kenkyu No... Dec 2023And Then There Were None and Sparkling Cyanide, two of Agatha Christie's famous novels describe potassium cyanide-induced deaths. Cyanide, a tasteless, odorless,...
And Then There Were None and Sparkling Cyanide, two of Agatha Christie's famous novels describe potassium cyanide-induced deaths. Cyanide, a tasteless, odorless, strongly alkaline poison is a powerful gastrointestinal irritant, following oral ingestion. It reacts with hydrochloric acid in the gastric juice to produce hydrogen cyanide gas, which is absorbed and inhibits the mitochondrial electron transfer system and consequently suppresses adenosine triphosphate (ATP) production. Therefore, the central nervous system, which consumes a large amount of ATP, is first affected and symptoms of poisoning manifest as dizziness, disorientation, coma, and convulsions. The orally lethal dose is approximately 300 mg.
Topics: Humans; Cyanides; Antidotes; Seizures; Adenosine Triphosphate
PubMed: 38097219
DOI: 10.11477/mf.1416202529 -
Organic Letters May 2024A catalytic 1,1-dicarbofunctionalization of electron-deficient olefins was effected on the basis of the three-component coupling reactions involving olefins bearing...
A catalytic 1,1-dicarbofunctionalization of electron-deficient olefins was effected on the basis of the three-component coupling reactions involving olefins bearing vicinal electron-withdrawing groups, potassium cyanide, and an alkyl halide, which afforded geminally cyanoalkylated products in high yields via conjugate cyanation, 1,2-proton transfer, and enolate alkylation. The use of suitable chiral phase-transfer catalysts enabled asymmetric induction in this transformation.
PubMed: 38695395
DOI: 10.1021/acs.orglett.4c00866 -
International Journal of Toxicology Sep 2016The Food and Drug Administration Animal Rule requires evaluation of cardiovascular and central nervous system (CNS) effects of new therapeutics. To characterize an adult...
The Food and Drug Administration Animal Rule requires evaluation of cardiovascular and central nervous system (CNS) effects of new therapeutics. To characterize an adult and juvenile mouse model, neurobehavioral and cardiovascular effects and pathology of a single sublethal but toxic, 8 mg/kg, oral dose of potassium cyanide (KCN) for up to 41 days postdosing were investigated. This study describes the short- and long-term sensory, motor, cognitive, and behavioral changes associated with oral dosing of a sublethal but toxic dose of KCN utilizing functional observation battery and Tier II CNS testing in adult and juvenile mice of both sexes. Selected tissues (histopathology) were evaluated for changes associated with KCN exposure with special attention to brain regions. Telemetry (adult mice only) was used to evaluate cardiovascular and temperature changes. Neurobehavioral capacity, sensorimotor responsivity or spontaneous locomotor activity, and rectal temperature were significantly reduced in adult and juvenile mice at 30 minutes post-8 mg/kg KCN dose. Immediate effects of cyanide included bradycardia, adverse electrocardiogram arrhythmic events, hypotension, and hypothermia with recovery by approximately 1 hour for blood pressure and heart rate effects and by 2 hours for body temperature. Lesions consistent with hypoxia, such as mild acute tubular necrosis in the kidneys corticomedullary junction, were the only histopathological findings and occurred at a very low incidence. The mouse KCN intoxication model indicates rapid and completely reversible effects in adult and juvenile mice following a single oral 8 mg/kg dose. Neurobehavioral and cardiovascular measurements can be used in this animal model as a trigger for treatment.
Topics: Administration, Oral; Animals; Behavior, Animal; Blood Pressure; Brain; Cardiovascular System; Disease Models, Animal; Electrocardiography; Female; Heart Rate; Lethal Dose 50; Male; Mice; Mice, Inbred Strains; Nervous System; Neurons; Potassium Cyanide
PubMed: 27170681
DOI: 10.1177/1091581816646974 -
Journal of Applied Microbiology Sep 2022Agriculture faces challenges to fulfil the rising food demand due to shortage of arable land and various environmental stressors. Traditional farming technologies help... (Review)
Review
Agriculture faces challenges to fulfil the rising food demand due to shortage of arable land and various environmental stressors. Traditional farming technologies help in fulfilling food demand but they are harmful to humans and environmental sustainability. The food production along with agro-environmental sustainability could be achieved by encouraging farmers to use agro-environmental sustainable products such as biofertilizers and biopesticides consisting of live microbes or plant extract instead of chemical-based inputs. The eco-friendly formulations play a significant role in plant growth promotion, crop yield and repairing degraded soil texture and fertility sustainably. Mineral solubilizing microbes that provide vital nutrients like phosphorus, potassium, zinc and selenium are essential for plant growth and development and could be developed as biofertilizers. These microbes could be plant associated (rhizospheric, endophytic and phyllospheric) or inhabit the bulk soil and diverse extreme habitats. Mineral solubilizing microbes from soil, extreme environments, surface and internal parts of the plant belong to diverse phyla such as Ascomycota, Actinobacteria, Basidiomycota, Bacteroidetes, Chlorobi, Cyanobacteria, Chlorophyta, Euryarchaeota, Firmicutes, Gemmatimonadetes, Mucoromycota, Proteobacteria and Tenericutes. Mineral solubilizing microbes (MSMs) directly or indirectly stimulate plant growth and development either by releasing plant growth regulators; solubilizing phosphorus, potassium, zinc, selenium and silicon; biological nitrogen fixation and production of siderophores, ammonia, hydrogen cyanide, hydrolytic enzymes and bioactive compound/secondary metabolites. Biofertilizer developed using mineral solubilizing microbes is an eco-friendly solution to the sustainable food production system in many countries worldwide. The present review deals with the biodiversity of mineral solubilizing microbes, and potential roles in crop improvement and soil well-being for agricultural sustainability.
Topics: Agriculture; Bacteria; Fertilizers; Humans; Microbiota; Phosphorus; Plants; Potassium; Selenium; Soil; Soil Microbiology; Zinc
PubMed: 35588278
DOI: 10.1111/jam.15627 -
Marine Pollution Bulletin Sep 2022
Topics: Animals; Embryo, Nonmammalian; Potassium Cyanide; Sea Urchins
PubMed: 35872477
DOI: 10.1016/j.marpolbul.2022.113965 -
New Zealand Veterinary Journal Jun 2015Tuberculosis (TB) due to Mycobacterium bovis infection was first identified in brushtail possums (Trichosurus vulpecula) in New Zealand in the late 1960s. Since the... (Review)
Review
Tuberculosis (TB) due to Mycobacterium bovis infection was first identified in brushtail possums (Trichosurus vulpecula) in New Zealand in the late 1960s. Since the early 1970s, possums in New Zealand have been controlled as part of an ongoing strategy to manage the disease in livestock. The TB management authority (TBfree New Zealand) currently implements three strategic choices for disease-related possum control: firstly TB eradication in areas selected for eradication of the disease from livestock and wildlife, secondly Free Area Protection in areas in which possums are maintained at low densities, normally along a Vector Risk Area (VRA) boundary, and thirdly Infected Herd Suppression, which includes the remaining parts of VRA where possums are targeted to minimise the infection risk to livestock. Management is primarily through a range of lethal control options. The frequency and intensity of control is driven by a requirement to reduce populations to very low levels (usually to a trap-catch index below 2%), then to hold them at or below this level for 5-10 years to ensure disease eradication.Lethal possum control is implemented using aerial- and ground-based applications, under various regulatory and operational constraints. Extensive research has been undertaken aimed at improving the efficacy and efficiency of control. Aerial applications use sodium fluoroacetate (1080) bait for controlling possums over extensive and rugged areas of forest that are difficult to access by foot. Ground-based control uses a range of toxins (primarily, a potassium cyanide-based product) and traps. In the last 5 years there has been a shift from simple possum population control to the collection of spatial data on possum presence/absence and relative density, using simple possum detection devices using global positioning system-supported data collection tools, with recovery of possum carcasses for diagnostic necropsy. Such data provide information subsequently used in predictive epidemiological models to generate a probability of TB freedom.The strategies for managing TB in New Zealand wildlife now operate on four major principles: firstly a target threshold for possum population reduction is defined and set, secondly an objective methodology is applied for assessing whether target reductions have been achieved, thirdly effective control tools for achieving possum population reductions are used, and fourthly the necessary legislative support is in place to ensure compliance. TBfree New Zealand's possum control programme meets these requirements, providing an excellent example of an effective pest and disease control programme.
Topics: Animals; Introduced Species; Mycobacterium bovis; New Zealand; Population Surveillance; Trichosurus; Tuberculosis
PubMed: 25582863
DOI: 10.1080/00480169.2014.981315 -
The American Journal of Forensic... Dec 2014In the spring of 1944, Kurt von Gottberg, the SS police chief in Minsk, was shot and injured by 2 Soviet agents. Although he was only slightly injured, he died 6 hours...
In the spring of 1944, Kurt von Gottberg, the SS police chief in Minsk, was shot and injured by 2 Soviet agents. Although he was only slightly injured, he died 6 hours later. The bullets were hollow and contained a crystalline white powder. They were 4-g bullets, semi-jacketed in cupronickel, containing 28 mg of aconitine. They were later known as akonitinnitratgeschosse. The Sipo (the Nazi security police) then ordered a trial with a 9-mm Parabellum cartridge containing Ditran, an anticholinergic drug with hallucinogenic properties causing intense mental confusion. In later years, QNB was used and given the NATO code BZ (3-quinuclidinyl-benzylate). It was proven that Saddam Hussein had this weapon (agent 15) manufactured and used it against the Kurds. Serbian forces used the same type of weapon in the Bosnian conflict, particularly in Srebrenica.The authors go on to list the Cold War toxic weapons developed by the KGB and the Warsaw pact countries for the discreet elimination of dissidents and proindependence leaders who had taken refuge in the West. These weapons include PSZh-13 launchers, the Troika electronic sequential pistol, and the ingenious 4-S110T captive piston system designed by the engineer Stechkin. Disguised as a cigarette case, it could fire a silent charge of potassium cyanide. This rogues gallery also includes the umbrella rigged to inject a pellet of ricin (or another phytalbumin of similar toxicity, such as abrin or crotin) that was used to assassinate the Bulgarian writer and journalist Georgi Markov on September 7, 1978, in London.During the autopsy, the discovery of a bullet burst into 4 or 5 parts has to make at once suspecting the use of a toxic substance. Toxicological analysis has to look for first and foremost aconitine, cyanide, suxamethonium, Ditran, BZ, or one of the toxic phytalbumins. The use of such complex weapons has to make suspect a powerful organization: army, secret service, terrorism. The existence of the Russian UDAR spray gun in the present day, however, shows that these weapons are still present. The possibility that one might be used to spray a charge of cyanide is still very real, especially as it would not be very difficult for an informed amateur to produce homemade toxic ammunition by adapting existing civil or military cartridges.
Topics: Chemical Warfare; Chemical Warfare Agents; Europe; Firearms; Forensic Ballistics; History, 20th Century; Humans; Russia; World War II; Wounds, Gunshot
PubMed: 25354227
DOI: 10.1097/PAF.0b013e318288abe8