Page last updated: 2024-10-24

DNA cytosine deamination

Definition

Target type: biologicalprocess

The removal of an amino group from a cytosine residue in DNA, forming a uracil residue. [GOC:mah]

DNA cytosine deamination is a spontaneous chemical reaction that converts cytosine (C) to uracil (U) in DNA. This process is a major source of mutations, as uracil is not a normal component of DNA and its presence can lead to mispairing with adenine (A) during replication, resulting in a C-to-T transition mutation.

Deamination can occur through several mechanisms, including:

* **Hydrolytic deamination:** This is the most common mechanism and involves the attack of water on the amino group of cytosine. This reaction is catalyzed by heat and can occur spontaneously in DNA.
* **Deamination by enzymes:** Certain enzymes, such as APOBEC family members, can deaminate cytosine in DNA, often as part of the immune response. These enzymes can target specific sequences and contribute to the generation of mutations in cancer.

The presence of uracil in DNA is recognized by DNA repair systems, such as the base excision repair (BER) pathway. The BER pathway involves the removal of uracil by uracil-DNA glycosylase (UNG), followed by replacement with cytosine.

If uracil is not repaired, it can lead to a C-to-T transition mutation during replication. This can have significant consequences, as it can alter the coding sequence of genes and lead to changes in protein function.

In addition to its role in mutagenesis, DNA cytosine deamination has also been implicated in various biological processes, including:

* **Immune system:** APOBEC enzymes are involved in the immune response and can target viral DNA to restrict infection.
* **Cancer:** Deamination can contribute to the development of cancer by generating mutations that drive tumor growth.
* **Evolution:** Deamination can be a source of genetic variation and contribute to the evolutionary process.'
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Proteins (1)

ProteinDefinitionTaxonomy
Single-stranded DNA cytosine deaminaseA single-stranded DNA cytosine deaminase that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q9GZX7]Homo sapiens (human)

Compounds (33)

CompoundDefinitionClassesRoles
hydroxylamineamino alcohol : An alcohol containing an amino functional group in addition to the alcohol-defining hydroxy group.hydroxylaminesalgal metabolite;
bacterial xenobiotic metabolite;
EC 1.1.3.13 (alcohol oxidase) inhibitor;
EC 4.2.1.22 (cystathionine beta-synthase) inhibitor;
EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor;
nitric oxide donor;
nucleophilic reagent
aurintricarboxylic acidaurintricarboxylic acid : A member of the class of quinomethanes that is 3-methylidene-6-oxocyclohexa-1,4-diene-1-carboxylic acid in which the methylidene hydrogens are replaced by 4-carboxy-3-hydroxyphenyl groups. The trisodium salt is the biological stain 'chrome violet CG' while the triammonium salt is 'aluminon'.

Aurintricarboxylic Acid: A dye which inhibits protein biosynthesis at the initial stages. The ammonium salt (aluminon) is a reagent for the colorimetric estimation of aluminum in water, foods, and tissues.
monohydroxybenzoic acid;
quinomethanes;
tricarboxylic acid
fluorochrome;
histological dye;
insulin-like growth factor receptor 1 antagonist
chelerythrinechelerythrine : A benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae.benzophenanthridine alkaloid;
organic cation
antibacterial agent;
antineoplastic agent;
EC 2.7.11.13 (protein kinase C) inhibitor
dequaliniumdequalinium : A quinolinium ion comprising decane in which one methyl hydrogen at each end of the molecule has been replaced by a 4-amino-2-methylquinolin-1-yl group.

Dequalinium: A topical bacteriostat that is available as various salts. It is used in wound dressings and mouth infections and may also have antifungal action, but may cause skin ulceration.
quinolinium ionantifungal agent;
antineoplastic agent;
antiseptic drug;
mitochondrial NADH:ubiquinone reductase inhibitor
diphenyleneiodoniumdibenziodolium : An organic cation that is fluorene in which the methylene group is replaced by a positively charged iodine.

diphenyleneiodonium: structure in first source; NADPH oxidase inhibitor
organic cation
dipyridamoledipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.

Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)
piperidines;
pyrimidopyrimidine;
tertiary amino compound;
tetrol
adenosine phosphodiesterase inhibitor;
EC 3.5.4.4 (adenosine deaminase) inhibitor;
platelet aggregation inhibitor;
vasodilator agent
2,3-dimethoxy-1,4-naphthoquinone2,3-dimethoxynaphthalene-1,4-dione : A naphthoquinone that is 1,4-naphthoquinone bearing two methoxy substituents at positions 2 and 3. Redox-cycling agent that induces intracellular superoxide anion formation and, depending on the concentration, induces cell proliferation, apoptosis or necrosis. Used to study the role of ROS in cell toxicity, apoptosis, and necrosis.1,4-naphthoquinones
hydralazinehydralazine : The 1-hydrazino derivative of phthalazine; a direct-acting vasodilator that is used as an antihypertensive agent.

Hydralazine: A direct-acting vasodilator that is used as an antihypertensive agent.
azaarene;
hydrazines;
ortho-fused heteroarene;
phthalazines
antihypertensive agent;
vasodilator agent
phenelzinePhenelzine: One of the MONOAMINE OXIDASE INHIBITORS used to treat DEPRESSION; PHOBIC DISORDERS; and PANIC.primary amine
beta-lapachonebeta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.

beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase
benzochromenone;
orthoquinones
anti-inflammatory agent;
antineoplastic agent;
plant metabolite
mitoxantronemitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.

Mitoxantrone: An anthracenedione-derived antineoplastic agent.
dihydroxyanthraquinoneanalgesic;
antineoplastic agent
protoporphyrin ixprotoporphyrin : A cyclic tetrapyrrole that consists of porphyrin bearing four methyl substituents at positions 3, 8, 13 and 17, two vinyl substituents at positions 7 and 12 and two 2-carboxyethyl substituents at positions 2 and 18. The parent of the class of protoporphyrins.

protoporphyrin IX: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7685
sanguinarinebenzophenanthridine alkaloid : A specific group of isoquinoline alkaloids that occur only in higher plants and are constituents mainly of the Papaveraceae family.alkaloid antibiotic;
benzophenanthridine alkaloid;
botanical anti-fungal agent
tyrphostin a9alkylbenzenegeroprotector
1-naphthaldehyde1-naphthaldehyde : A naphthaldehyde with a formyl group at position 1.

1-naphthaldehyde: structure

naphthaldehyde : An aldehyde in which the organyl group is a naphthyl group.
naphthaldehydemouse metabolite
pyrazolanthroneanthra[1,9-cd]pyrazol-6(2H)-one : A member of the class of anthrapyrazoles that is anthra[1,9-cd]pyrazole substituted at position 6 by an oxo group. An inhibitor of c-Jun N-terminal kinase.

pyrazolanthrone: JNK (c-Jun N-terminal kinase) inhibitor; structure in first source
anthrapyrazole;
aromatic ketone;
cyclic ketone
antineoplastic agent;
c-Jun N-terminal kinase inhibitor;
geroprotector
2,3,5-trimethylquinol2,3,5-trimethylhydroquinone : A member of the class of hydroquinones that is hydroquinone substituted by methyl groups at positions 2, 3 and 5.

2,3,5-trimethylquinol: reducing agent
hydroquinones;
methylbenzene
idarubicinIdarubicin: An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.anthracycline antibiotic;
deoxy hexoside;
monosaccharide derivative
flupirtineflupirtine: RN given refers to parent cpd without isomeric designationaminopyridine
masoprocolmasoprocol : The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.

Masoprocol: A potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.
nordihydroguaiaretic acidantineoplastic agent;
hypoglycemic agent;
lipoxygenase inhibitor;
metabolite
2-(4-aminophenyl)quinoline2-(4-aminophenyl)quinoline: used for imaging tau protein; structure in first source
IPA-3IPA-3 : An organic disulfide obtained by oxidative dimerisation of 1-sulfanylnaphthalen-2-ol.naphthols;
organic disulfide
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
2-[[2-methyl-5-(3-methyl-4-oxo-1-phthalazinyl)phenyl]sulfonylamino]acetic acid ethyl esteralpha-amino acid ester
(2'-(4-aminophenyl)-(2,5'-bi-1h-benzimidazol)-5-amine)benzimidazoles
nemadipine-anemadipine-A : A dihydropyridine that is that is 1,4-dihydropyridine which is substituted at positions 2 and 6 by methyl groups, at positions 3 and 5 by ethoxycarbonyl groups, and at position 4 by a pentafluorophenyl group. An L-type calcium channel alpha1-subunit antagonist. When exposed to the microscopic soil nematode Caenorhabditis elegans, nemadipine-A induces a variety of defects including those affecting morphology and egg laying.

nemadipine-A: structure in first source
dicarboxylic acids and O-substituted derivatives;
diester;
dihydropyridine;
ethyl ester;
pentafluorobenzenes
calcium channel blocker
5-[[(1-cyclohexyl-5-tetrazolyl)thio]methyl]-3-phenyl-1,2,4-oxadiazoleoxadiazole;
ring assembly
ro 41-0960
tectochrysintectochrysin : A monohydroxyflavone that is flavone substituted by a hydroxy group at position 4 and a methoxy group at position 7 respectively.

tectochrysin: structure in first source
monohydroxyflavone;
monomethoxyflavone
antidiarrhoeal drug;
antineoplastic agent;
plant metabolite
casein kinase iiCasein Kinase II: A ubiquitous casein kinase that is comprised of two distinct catalytic subunits and dimeric regulatory subunit. Casein kinase II has been shown to phosphorylate a large number of substrates, many of which are proteins involved in the regulation of gene expression.
2-(2-methoxyanilino)-8-[(3-methyl-1-piperidinyl)-oxomethyl]-[1,3,4]thiadiazolo[2,3-b]quinazolin-5-oneN-acylpiperidine
CDN1163CDN1163 : A secondary carboxamide resulting from the formal condensation of the carboxy group of 4-isopropoxybenzoic acid with the primary amino group of 2-methylquinolin-8-amine. An allosteric activator of sarco/endoplasmic reticulum Ca(2+)-ATPase (SERCA).

CDN1163: a SERCA2 activator with antidiabetic activity; structure in first source
aromatic ether;
quinolines;
secondary carboxamide
SERCA activator
hispidinhispidin : Fungal metabolite first found in basidiomycete Inonotus hispidus (formerly Polyporus hispidus).

hispidin: metabolite of Basidiomycete Polyporus hispidus
2-pyranones;
catechols
antioxidant;
EC 2.7.11.13 (protein kinase C) inhibitor;
fungal metabolite
4-[[(4-oxo-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-2-yl)thio]methyl]benzoic acid methyl esterbenzoate ester