Macrocycles

Phthalocyanine ('''''') is a large, aromatic, macrocyclic, organic compound with the formula and is of theoretical or specialized interest in chemical dyes and photoelectricity.

class=skin-invert-image|thumb|240px|Erythromycin, a [[macrolide antibiotic, is one of many naturally occurring macrocycles.]] Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry.

thumb|upright=2.0|Chemical structure of the three main types of cyclodextrins. Cyclodextrins are a family of cyclic oligosaccharides, consisting of a macrocyclic ring of glucose subunits joined by α-1,4 glycosidic bonds. Cyclodextrins are produced from starch by enzymatic conversion. They are used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.

Abamectin (also called avermectin B1) is a widely used insecticide and anthelmintic. Abamectin, is a member of the avermectin family and is a natural fermentation product of soil dwelling actinomycete Streptomyces avermitilis. Abamectin differs from ivermectin, the popular member of the avermectin family, by a double bond between carbons 22 and 23. Fermentation of Streptomyces avermitilis yields eight closely related avermectin homologs, with the B1a and B1b forms comprising the majority of the fermentation. The non-proprietary name, abamectin, refers to a mixture of B1a (~80%) and B1b (~20%).

Civetone is a macrocyclic ketone and the main odorous constituent of civet oil. It is a pheromone sourced from the African civet. It has a strong musky odor that becomes pleasant at extreme dilutions. Civetone is closely related to muscone, the principal odoriferous compound found in musk; the structure of both compounds was elucidated by Leopold Ružička. Today, civetone can be synthesized from precursor chemicals found in palm oil.

Corrin is a heterocyclic compound. Although not known to exist on its own, the molecule is of interest as the parent macrocycle related to the cofactor and chromophore in vitamin B12. Its name reflects that it is the "core" of vitamin B12 (cobalamins). Compounds with a corrin core are known as "corrins".

chemical compound

18-Crown-6 is an organic compound with the formula [C2H4O]6 and the IUPAC name of 1,4,7,10,13,16-hexaoxacyclooctadecane. It is a white, hygroscopic crystalline solid with a low melting point. Like other crown ethers, 18-crown-6 functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 106 M−1). The point group of 18-crown-6 is S6. The dipole moment of 18-crown-6 is solvent- and temperature-dependent. Below 25 °C, the dipole moment of 18-crown-6 is in cyclohexane and in benzene. The synthesis of the crown ethers led to

Porphine or porphin is an organic compound of empirical formula . It is heterocyclic and aromatic. The molecule is a flat macrocycle, consisting of four pyrrole-like rings joined by four methine bridges, which makes it the simplest of the tetrapyrroles.

Muscone is a macrocyclic ketone, an organic compound that is the primary contributor to the odor of deer musk. Natural muscone is obtained from musk, a glandular secretion of the musk deer, which has been used in perfumery and medicine for thousands of years. Since obtaining natural musk requires killing the endangered animal, nearly all muscone used in perfumery and for scenting consumer products today is synthetic. It has the characteristic smell of being "musky" (described as "musk, animal, powdery").

Eribulin, sold under the brand name Halaven among others, is an anti-cancer medication used to treat breast cancer and liposarcoma.

Simeprevir, sold under the brand name Olysio among others, is a medication used in combination with other medications for the treatment of hepatitis C. It is specifically used for hepatitis C genotype 1 and 4. Medications it is used with include sofosbuvir or ribavirin and peginterferon-alfa. Cure rates are in 80s to 90s percent. It may be used in those who also have HIV/AIDS. It is taken by mouth once daily for typically 12 weeks.

thumbnail|230px|Crystal structure of a catenane with a cyclobis(paraquat-p-phenylene)|cyclobis(paraquat-p-phenylene) [[macrocycle reported by Stoddart and coworkers. ]]

chemical compound

[[Image:Models of cucurbiturils.jpg|thumbnail|400px|Computer models of CB[5], CB[6], and CB[7]. Top row is the view into the cavity and the bottom is the side view]]

Enterobactin (also known as enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.

Tetraphenylporphyrin, abbreviated TPP or H2TPP, is a synthetic heterocyclic compound that resembles naturally occurring porphyrins. Porphyrins are dyes and cofactors found in hemoglobin and cytochromes and are related to chlorophyll and vitamin B12. The study of naturally occurring porphyrins is complicated by their low symmetry and the presence of polar substituents. Tetraphenylporphyrin is hydrophobic, symmetrically substituted, and easily synthesized. The compound is a dark purple solid that dissolves in nonpolar organic solvents such as chloroform and benzene.

Cyclen (1,4,7,10-tetraazacyclododecane) is an aza-crown ether with the formula (CH2CH2NH)4. It is a white solid. It forms coordination complexes with metal cations and is used to synthesize the chelating agent DOTA which has several medical applications. Being structurally simple, symmetrical, and polyfunctional, cyclen has been widely investigated.

chemical compound

class of chemical compounds

Paritaprevir (previously known as ABT-450) is an acylsulfonamide inhibitor of the NS3-4A serine protease manufactured by Abbott Laboratories that shows promising results as a treatment of hepatitis C. When given in combination with ritonavir and ribavirin for 12 weeks, the rate of sustained virologic response at 24 weeks after treatment has been estimated to be 95% for those with hepatitis C virus genotype 1. Resistance to treatment with paritaprevir is uncommon, because it targets the binding site, but has been seen to arise due to mutations at positions 155 and 168 in NS3.

Grazoprevir is a drug approved for the treatment of hepatitis C. It was developed by Merck and completed Phase III trials, used in combination with the NS5A replication complex inhibitor elbasvir under the trade name Zepatier, either with or without ribavirin.

1,4,7-Triazacyclononane, known as "TACN" which is pronounced "tack-en," is an aza-crown ether with the formula (C2H4NH)3. TACN is derived, formally speaking, from cyclononane by replacing three equidistant CH2 groups with NH groups. TACN is one of the oligomers derived from aziridine, C2H4NH. Other members of the series include piperazine, C4H8(NH)2, and the cyclic tetramer 1,4,7,10-tetraazacyclododecane.

Cyclam (1,4,8,11-tetraazacyclotetradecane) is an organic compound with the formula (NHCH2CH2NHCH2CH2CH2)2. Classified as an aza-crown ether, it is a white solid that is soluble in water. As a macrocyclic ligand, it binds strongly to many transition metal cations. The compound was first prepared by the reaction of 1,3-dibromopropane and ethylenediamine. thumb|left|Structure of one isomer of trans-Ni(cyclam)Cl2. The compound features four secondary amines. Its complexes therefore can exist as several diastereomers, depending on the relative orientation of the N–H centres. Its complexes feature

Edotreotide (USAN, also known as (DOTA0-Phe1-Tyr3) octreotide, DOTA-TOC, DOTATOC) is a substance which, when bound to various radionuclides, is used in the treatment and diagnosis of certain types of cancer. When used therapeutically it is an example of peptide receptor radionuclide therapy.

chelate of Lu-177 with DOTA-TATE, a peptide derivative bound to a DOTA molecule

Carpaine is the major piperidine alkaloid component of papaya leaves which has been studied for potential medicinal effects. Carpaine extracted from Carica papaya trees has been reported to have diverse biological properties, such as anti-malarial, anti-inflammatory, anti-oxidant, and vasodilatory effects. Especially, Carpaine possessed significant anti-plasmodial activity in vitro (IC50 of 0.2 μM) and high selectivity towards the parasites.

1,4,7-Trithiacyclononane, also called 9-ane-S3, is the thia-crown ether with the formula (CH2CH2S)3. This cyclic thioether is most often encountered as a tridentate ligand in coordination chemistry, where it forms transition metal thioether complexes.

Vaniprevir (MK-7009) is a macrocyclic hepatitis C virus (HCV) NS3/4A protease inhibitor, developed by Merck & Co., which is currently in clinical testing. In Japan, it was approved for treating hepatitis C in 2014 under the brand name Vanihep.

Cyclododecanone is an organic compound with the formula (CH2)11CO. It is a cyclic ketone that exists as a white solid at room temperature. Like its smaller analogs but unlike the larger ones, it has a camphor-like odor. ==History and synthesis== It was first obtained by Ružička et al. in 1926 by ketonic decarboxylation. A higher-yield method by acyloin condensation was devised by Prelog et al. in 1947.

NIM811 is a mitochondrial permeability transition inhibitor. Also known as '''N-methyl-4-isoleucine cyclosporin''', it is a substituted cyclosporine analog that binds to cyclophilin; however, this binary complex cannot bind to calcineurin, and therefore lacks immunosuppressive activity.

200px|right|thumb|Cobalamin structure includes a deprotonated [[corrin macrocycle.]] A corrole is an aromatic tetrapyrrole. The corrin ring is also present in cobalamin (vitamin B12). The ring consists of nineteen carbon atoms, with four nitrogen atoms in the core of the molecule. In this sense, corrole is very similar to porphyrin.

Cilengitide (EMD 121974) is a molecule designed and synthesized at the Technical University Munich in collaboration with Merck KGaA in Darmstadt. It is based on the cyclic peptide cyclo(-RGDfV-), which is selective for αv integrins, which are important in angiogenesis (forming new blood vessels), and other aspects of tumor biology. Hence, it is under investigation for the treatment of glioblastoma, where it may act by inhibiting angiogenesis, and influencing tumor invasion and proliferation.

α-Cyclodextrin (alpha-cyclodextrin), sometimes abbreviated as α-CD, is a hexasaccharide derived from glucose. It is related to the β- (beta) and γ- (gamma) cyclodextrins, which contain seven and eight glucose units, respectively. All cyclodextrins are white, water-soluble solids with minimal toxicity. Cyclodextrins tend to bind other molecules in their quasi-cylindrical, lipophilic interiors. The compound is of wide interest because it exhibits host–guest properties, forming inclusion compounds. This inclusion (and release) behavior leads to applications in medicine.

thumb|Molecular structures of iGDGTs containing 0 to 4 cyclopentane rings (GDGT-0 to GDGT-4). Caldarchaeol is a membrane-spanning lipid of the isoprenoid glycerol dialkyl glycerol tetraether (iGDGT) class, produced and used by archaea. Membranes made up of caldarchaeol are more stable since the hydrophobic chains are linked together (as compared to lipid bilayer structures in eukaryotes and bacteria), allowing archaea to withstand extreme conditions.

DOTA-TATE (DOTATATE, DOTA-octreotate, oxodotreotide, DOTA-(Tyr3)-octreotate, and DOTA-0-Tyr3-Octreotate) is an eight amino acid long peptide, with a covalently bonded DOTA bifunctional chelator.

17-Dimethylaminoethylamino-17-demethoxygeldanamycin (17-DMAG) is a chemical compound which is a semi-synthetic derivative of the antibiotic geldanamycin. It is being studied for the possibility of treating cancer.

Danoprevir (INN) is an orally available 15-membered macrocyclic peptidomimetic inhibitor of NS3/4A HCV protease. It contains acylsulfonamide, fluoroisoindole and tert-butyl carbamate moieties. Danoprevir is a clinical candidate based on its favorable potency profile against multiple HCV genotypes 1–6 and key mutants (GT1b, IC50 = 0.2–0.4 nM; replicon GT1b, EC50 = 1.6 nM). Danoprevir has been evaluated in an open-label, single arm clinical trial in combination with ritonavir for treating COVID-19 and favourably compared to lopinavir/ritonavir in a second trial.

Telomestatin is a macrocyclic chemical compound that acts by inhibiting the telomerase activity of in vitro cancer cells. It was first isolated from the bacteria Streptomyces anulatus. Telomestatin induces the formation of basket-type G-quadruplex (G4) structures from hybrid-type G-quadruplexes in the telomeric region. Upon formation of G4 structure there will be a decrease in the activity of the telomerase, which is involved in the replication of the telomeres and as a result the cell dies due to Hayflick type senescence.

Cresomycin is an experimental antibiotic. It binds to the bacterial ribosome in both Gram-negative and Gram-positive bacteria, and it has been found to be effective against multi-drug-resistant stains of Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. It belongs to the bridged macrobicyclic oxepanoprolinamide antibiotics, which have similarities with lincosamides antibiotics.

21-Crown-7 is an organic compound with the formula (C2H4O)7. Similar to other crown ethers, 21-crown-7 functions as a ligand for certain metal cations, with a specific affinity for caesium cations. The dipole moment of 21-crown-7 varies depending on the solvent and temperatures.

chemical compound

Cavicularin is a natural phenolic secondary metabolite isolated from the liverwort Cavicularia densa. This macrocycle is unusual because it was the first compound isolated from nature displaying optical activity solely due to the presence of planar chirality and axial chirality. The specific rotation for (+)-cavicularin is +168.2°. It is also a very strained molecule. The para-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat boat-like geometry. This type of angle strain in aromatic compounds is normally reserved for synthetic cyclophanes.