quaternary ammonium group binding
Definition
Target type: molecularfunction
Binding to a quaternary ammonium group, including glycine betaine, choline, carnitine and proline. A quaternary ammonium group is any compound that can be regarded as derived from ammonium hydroxide or an ammonium salt by replacement of all four hydrogen atoms of the NH4+ ion by organic groups. [GOC:ai]
Quaternary ammonium group binding is a molecular function that describes the ability of a molecule to interact with a quaternary ammonium group. This group, consisting of a nitrogen atom bonded to four alkyl groups, carries a positive charge and is often found in biomolecules such as acetylcholine, choline, and other neurotransmitters. The binding of quaternary ammonium groups is crucial for a variety of biological processes, including:
* **Neurotransmission:** Quaternary ammonium groups are key components of neurotransmitters, which transmit signals between neurons. For example, acetylcholine binds to receptors on muscle cells, triggering muscle contraction.
* **Enzyme activity:** Many enzymes rely on quaternary ammonium groups to bind substrates and catalyze reactions. For instance, acetylcholinesterase, an enzyme that breaks down acetylcholine, has a quaternary ammonium group in its active site that specifically interacts with the neurotransmitter.
* **Drug action:** Many drugs target quaternary ammonium groups, either to mimic or block the effects of natural neurotransmitters. For example, anticholinergic drugs, which block the action of acetylcholine, can be used to treat conditions like Parkinson's disease.
* **Cellular signaling:** Quaternary ammonium groups can also play a role in cellular signaling pathways. For example, some cell surface receptors bind to quaternary ammonium groups on signaling molecules, leading to downstream signaling events.
The specific molecular interactions that occur during quaternary ammonium group binding can vary depending on the molecule involved. However, common interactions include electrostatic interactions between the positively charged quaternary ammonium group and negatively charged groups on the binding molecule, as well as van der Waals interactions between the alkyl groups of the quaternary ammonium group and hydrophobic regions on the binding molecule.
Overall, quaternary ammonium group binding is a fundamental molecular function that plays a crucial role in a wide range of biological processes.'
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Proteins (2)
| Protein | Definition | Taxonomy |
|---|---|---|
| Neuronal acetylcholine receptor subunit alpha-2 | A neuronal acetylcholine receptor subunit alpha-2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q15822] | Homo sapiens (human) |
| Neuronal acetylcholine receptor subunit beta-2 | A neuronal acetylcholine receptor subunit beta-2 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P17787] | Homo sapiens (human) |
Compounds (57)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| nornicotine | nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure | ||
| bupropion | bupropion : An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring. Bupropion: A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE. | aromatic ketone; monochlorobenzenes; secondary amino compound | antidepressant; environmental contaminant; xenobiotic |
| 3-(1-methylpyrrolidin-2-yl)pyridine | 3-(1-methylpyrrolidin-2-yl)pyridine : An N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. | N-alkylpyrrolidine; pyridine alkaloid; pyrrolidine alkaloid | |
| epibatidine | alkaloid | ||
| dimethylphenylpiperazinium iodide | piperazines | ||
| anabasine | piperidine alkaloid; pyridine alkaloid | nicotinic acetylcholine receptor agonist; plant metabolite; teratogenic agent | |
| carbamylcholine | |||
| granisetron | aromatic amide; indazoles | ||
| isoflurane | Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects. | organofluorine compound | inhalation anaesthetic |
| mecamylamine | Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool. | primary aliphatic amine | |
| n-methylcarbamylcholine | N-methylcarbamylcholine: structure given in first source | ||
| ondansetron | Ondansetron: A competitive serotonin type 3 receptor antagonist. It is effective in the treatment of nausea and vomiting caused by cytotoxic chemotherapy drugs, including cisplatin, and has reported anxiolytic and neuroleptic properties. | carbazoles | |
| tilorone | tilorone : A member of the class of fluoren-9-ones that is 9H-fluoren-9-one which is substituted by a 2-(diethylamino)ethoxy group at positions 2 and 7. It is an interferon inducer and a selective alpha7 nicotinic acetylcholine receptor (alpha7 nAChR) agonist. Its hydrochloride salt is used as an antiviral drug. Tilorone: An antiviral agent used as its hydrochloride. It is the first recognized synthetic, low-molecular-weight compound that is an orally active interferon inducer, and is also reported to have antineoplastic and anti-inflammatory actions. | aromatic ether; diether; fluoren-9-ones; tertiary amino compound | anti-inflammatory agent; antineoplastic agent; antiviral agent; interferon inducer; nicotinic acetylcholine receptor agonist |
| tetramethylammonium | tetramethylammonium : The simplest quaternary ammonium cation, comprising a central nitrogen linked to four methyl groups. tetramethylammonium: RN given refers to parent cpd | quaternary ammonium ion | |
| indopan | alpha-methyltryptamine : A tryptamine derivative having a methyl substituent at the alpha-position. indopan: RN given refers to parent cpd without isomeric designation | tryptamines | |
| boldine | aporphine alkaloid | ||
| cytisine | alkaloid; bridged compound; lactam; organic heterotricyclic compound; secondary amino compound | nicotinic acetylcholine receptor agonist; phytotoxin; plant metabolite | |
| anatabine | anatabine: alkaloid found in tobacco; structure | bipyridines | |
| dihydro-beta-erythroidine | dihydro-beta-erythroidine : An organic heterotetracyclic compound resulting from the partial hydrogenation of the 1,3-diene moiety of beta-erythroidine to give the corresponding 2-ene. Dihydro-beta-Erythroidine: Dihydro analog of beta-erythroidine, which is isolated from the seeds and other plant parts of Erythrina sp. Leguminosae. It is an alkaloid with curarimimetic properties. | delta-lactone; organic heterotetracyclic compound; tertiary amino compound | nicotinic antagonist |
| polygodial | aldehyde | ||
| N-methyl-N-(3-pyridylmethyl)amine | aralkylamine | ||
| nicotine | (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum. | 3-(1-methylpyrrolidin-2-yl)pyridine | anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic |
| lobeline | (-)-lobeline : An optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position. | aromatic ketone; piperidine alkaloid; tertiary amine | nicotinic acetylcholine receptor agonist |
| 3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole | 3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole: structure in first source | ||
| philanthotoxin 343 | philanthotoxin 343: structure given in first source (see article's footnote); identical to philanthotoxin 433 except that the number of methylene groups between the respective amine moieties is 3,4,3 instead of 4,3,3 | N-acyl-amino acid | |
| erysodine | erysodine : An erythrina alkaloid with formula C18H21NO3 isolated from several erythrina plant species. It is a competitive antagonist of nicotinic acetylcholine receptors and exhibits antiparasitic and insecticidal activities. erysodine: structure given in first source | aromatic ether; diether; Erythrina alkaloid; organic heterotetracyclic compound; phenols | antiparasitic agent; nicotinic antagonist; phytogenic insecticide |
| varenicline | varenicline : An organic heterotetracyclic compound that acts as a partial agonist for nicotinic cholinergic receptors and is used (in the form of its tartate salt) as an aid to giving up smoking. Varenicline: A benzazepine derivative that functions as an ALPHA4-BETA2 NICOTINIC RECEPTOR partial agonist. It is used for SMOKING CESSATION. | ||
| pozanicline | |||
| anatoxin a | anatoxin a: found in Anabaena; was indexed to cyanobacterial toxin (MARINE TOXINS) 1978-2006; also see anatoxin-a(s) | tropane alkaloid | |
| deformylflustrabromine | deformylflustrabromine: has antineoplastic activity; isolated from Flustra folicea; structure in first source | tryptamines | |
| tropacocaine | tropacocaine: RN given refers to (exo)-isomer; structure | ||
| tropisetron | tropisetron : An indolyl carboxylate ester obtained by formal condensation of the carboxy group of indole-3-carboxylic acid with the hydroxy group of tropine. Tropisetron: An indole derivative and 5-HT3 RECEPTOR antagonist that is used for the prevention of nausea and vomiting. | indolyl carboxylic acid | |
| lobeline | |||
| epibatidine | |||
| anatoxin a | anatoxin I: found mainly in ANABAENA; was indexed to cyanobacterial toxin (MARINE TOXINS). isolated from many salt-tolerant freshwater cyanobacteria | ||
| abt 594 | |||
| 5-(6-chloro-3-pyridinyl)-9-azabicyclo[4.2.1]non-4-ene | azepine | ||
| trans-metanicotine | metanicotine: RN given refers to parent cpd with unspecified isomeric designation | ||
| a 85380 | A 85380: structure given in first source; A-85380 is the S-enantiomer; A-159470 is the R-enantiomer | ||
| ar-r 17779 | AR-R 17779: structure in first source | ||
| 3-(2,4-dimethoxybenzylidene)anabaseine | 3-(2,4-dimethoxybenzylidene)anabaseine: an alpha7nAChR nicotinic receptor agonist | dimethoxybenzene | |
| mg 624 | triethyl-(beta-4-stilbenoxyethyl)ammonium: inhibits alpha7 nicotinic receptors; structure in first source | ||
| 5-ia-85380 | aromatic ether | ||
| a 84543 | |||
| azd 0328 | spiro(1-azabicyclo(2.2.2)octane-3,2'(3H)-furo(2,3-b)pyridine): AZD-0328 is the (2'R)-isomer and D-tartrate salt; an alpha7 neuronal nicotinic receptor agonist; structure in first source | ||
| radafaxine | radafaxine: a bupropion metabolite; radafaxine is a (+)-isomer of hydroxybupropion | ||
| ispronicline | ispronicline: a neuronal nicotinic acetylcholine receptor modulator; has antidepressant, neuroprotective, and cognitive effects; structure in first source | ||
| 4-n-butyl-1-(4-(2-methylphenyl)-4-oxo-1-butyl)-piperidine hydrogen chloride | |||
| desnitroimidacloprid | desnitroimidacloprid: a nicotinic receptor agonist; structure in first source | ||
| dianicline | dianicline: an alpha4beta2 nicotinic receptor agonist; may be useful as an aid in quitting smoking; structure in first source | ||
| n-methylepibatidine | N-methylepibatidine: structure in first source | ||
| sazetidine-a | sazetidine-A: a ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them; structure in first source | ||
| ns 9283 | 3-(3-(pyridine-3-yl)-1,2,4-oxadiazol-5-yl)benzonitrile: an alpha4beta2 nAChR agonist | ||
| a-582941 | A-582941: nicotinic acetylcholine receptor (alpha7 nAChR) agonist | ||
| n,n-diallyl-5-methoxytryptamine | N,N-diallyl-5-methoxytryptamine: structure in first source | tryptamines | |
| imidacloprid | (E)-imidacloprid : The E-isomer of imidacloprid. | imidacloprid; imidazolidines; monochloropyridine | environmental contaminant; genotoxin; neonicotinoid insectide; nicotinic acetylcholine receptor agonist; xenobiotic |
| 3-(4-hydroxy-2-methoxybenzylidene)anabaseine |