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Information on EC 3.5.4.1 - cytosine deaminase
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3.5.4.1 cytosine deaminaseIUBMB Comments
Also acts on 5-methylcytosine.
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Word Map
- 3.5.4.1
- cytidine
- deaminases
- 5-fluorocytosine
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deamination
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prodrugs
- virion
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hypermutation
- viruses
- 5-fluorouracil
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apolipoprotein
- retroviruses
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suicide
- uracil
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retroviral
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apobecs
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single-stranded
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antiretroviral
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polypeptide-like
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mrna-editing
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g-to-a
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bystander
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activation-induced
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retrotransposons
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anti-hiv-1
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proviral
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retroelements
- lentiviruses
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encapsidation
- ganciclovir
- deoxycytidine
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retrotransposition
- ssdna
- fiv
- samhd1
-
cullin
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minus-strand
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replication-competent
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gene-directed
- sivmac
- medicine
-
line-1
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hsv-tk
- vpr
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gdept
-
non-ltr
- molecular biology
-
xenotropic
- analysis
- pharmacology
- biotechnology
- trim5alpha
- diagnostics
- proviruses
-
nickase
- agriculture
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single-cycle
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elongins
The enzyme appears in viruses and cellular organisms
Synonyms
apobec3g, apobec3, cytosine deaminase, apobec1, fca1p, isocytosine deaminase, coda protein, zn2+cdase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
APOBEC3
CD
CDA
CDase
codA
Cytosine aminohydrolase
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-
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cytosine deaminase
cytosine deaminase I
cytosine deaminase II
cytosine deaminase S
Fca1p
FCY1
isocytosine deaminase
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-
-
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yCD
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cytosine + H2O = uracil + NH3
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cytosine + H2O = uracil + NH3
active site architecture and substrate binding, catalytic mechanism
cytosine + H2O = uracil + NH3
substrate binding involves a significant conformational change that sequesters the reaction complex from solvent, active site architecture and substrate binding, catalytic mechanism
cytosine + H2O = uracil + NH3
E64 side-chain carboxyl group acts as proton shuttle between the Zn-bound water molecule and cytosine. In course of reaction, cytosine reorients to favor nucleophilic attack by a Zn-bound hydroxide. F114 may be important for reactant binding and product release
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
cytosine aminohydrolase
Also acts on 5-methylcytosine.
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CAS REGISTRY NUMBER
COMMENTARY
9025-05-2
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cytidine + H2O
1-beta-D-ribofuranosylpyrimidin-2(1H)-one + NH3
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-
-
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?
pyrimidin-2-one + H2O
(4R)-hydroxyl-3,4-dihydropyrimidine + ?
stabilization of a transition-state analogue at the active site of cytosine deaminase with importance of proton transfer from the Zn hydroxide group to Glu64 during the nucleophilic attack, quantum mechanical/molecular mechanical molecular dynamics and free energy simulations, active site structure, overview
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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209493, 209496, 209497, 209502, 209503, 209507, 209508, 667616, 670746, 684772, 685669, 685673, 685848, 685938, 687168, 688280, 688927, 711669, 719155
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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recombinant enzyme encoded in an adenoviral vector expressed in murine cancers or human cancer cell lines for prodrug cancer gene therapy, Ad/5HREp-BCD-mediated cytotoxicity under hypoxic conditions, overview
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
recombinant enzyme in transfected cells, cytotoxic effects of the enzyme expressed form the AdLPCD vector, overview
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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recombinant enzyme, combination of cytosine deaminase with uracil phosphoribosyl transferase leads to local and distant bystander effects against RM1 prostate cancer in mice in gene-directed enzyme prodrug therapy, overview
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
recombinant fusion enzyme, cytotoxicity could be enhanced by concurrently treating TKglyCD-expressing cells with prodrugs ganclocivir and 5-fluorocytosine, overview
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug to the cytotoxic drug in cancer therapy by recombinant adenoviral vector expressed enzyme in human glioma cells, leads to increased 5-fluorouracil-mediated cell killing, overview
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
activation of the prodrug to the cytotoxic drug in cancer therapy by recombinant enzyme, the cytosine deaminase gene acts as suicide gene leading to increased 5-fluorouracil-mediated murine colorectal cancer cell killing, liposomal formulation of substrate 5-fluorocytosine using dipalmitoylphopshatidylcholine and cholesterol in a 1:1 ratio, overview
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug to the cytotoxic drug in cancer therapy through the recombinant fusion enzyme cytosine deaminase/uracil phosphoribosyltransferase in human cancer cell lines, overview
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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direct inoculation of murine and human brain tumor cell lines, murine neuroblastoma and human glioma cells, with the enzyme transmitted in a recombinant HSV-1 viral oncolytic vector results in cytotoxicity and destruction of cancer cells wth increased cytotoxicity for neighbouring cells, overview
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
used as negative selection marker system, increased 5-fluorocytosine sensitivity in Streptomyces lividans
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
gene-directed enzyme prodrug therapy (GDEPT) with free and liposomal 5-fluorocytosine (5-FC), antitumor effects of liposomal 5-fluorocytosine (5-FC) increased if compared to free prodrug
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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recombinant enzyme expressed in Clostridium sp.
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug 5-fluorocytosine to the anticander drug 5-fluorouracil
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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release of 5-fluorouracil is rate-limiting and may involve multiple steps
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug by the recombinant fusion enzyme, overview
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
inside a cell, cytosine and 5-fluorocytosine compete for the active site of the enzyme
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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recombinant enzyme in gene therapy in human glioblastoma cell lines Y87-1 and Y87-2
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug to the cytotoxic drug in cancer therapy by recombinant enzyme in melanoma cells, leads to increased 5-fluorouracil-mediated cell killing, overview
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
activation of the prodrug to the cytotoxic drug in cancer therapy, gene therapy with the FCY1 gene, encoding the enzyme, alone is not effective in treatement of pancreatic cancer, co-expression with uracil phosphoribosyltranferase encoding gene FUR1, as fusion enzyme, can confer sensitivity to 5-fluorouracil to some pancreatic cancer cells, but not to all, thus it might also not be an effective therapy in pancreatic cancer, overview
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
activation of the prodrug, 5-fluorouracil is an inhibitor of DNA synthesis and RNA function
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug, product release is the rate-limiting step during the activation to the anticancer drug 5-fluorouracil
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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activation of the prodrug, the cytosine deaminase gene is an alternative gene for negative selection producing the toxic metabolite 5-fluorouracil, sensitivity of cells to 5-FU can be further increased by expression of uracil phosphoribosyltransferase, which catalyzes the conversion of 5-FU to 5-fluorouridine monophosphate
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
-
reaction of cytosine deaminase, the uracil phosphoribosyl transferase part in a chimeric bifunctional enzyme converts 5-fluorouracil into 5-fluoro-UMP, which is a precursor for the cell toxic 5-fluoro-UTP, used for negative selection of transgenic Plasmodium falciparum parasites
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-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
recombinant protein of cytosine deaminase used as antigen for biopanning approach, antibody-directed enzyme-prodrug therapy (GDEPT/ADEPT), binding of specific single chain fragment variable (scFv) with cytosine deaminase does not interfere with enzyme activity
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
recombinant cytosine deaminase in gene therapy, expression and function in transgenic cell lines and xenograft tumors
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
recombinant enzyme in gene therapy, expression analysis in transgenic mice with xenograft tumors, optical imaging technologies
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
-
?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
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?
5-fluorocytosine + H2O
5-fluorouracil + NH3
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-
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?
5-methylcytosine + H2O
thymine + NH3
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?
5-methylcytosine + H2O
thymine + NH3
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?
5-methylcytosine + H2O
thymine + NH3
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?
creatinine + H2O
N-methylhydantoin + NH3
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-
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?
cytosine + H2O
uracil + NH3
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137029, 209484, 209487, 209488, 209489, 209493, 209496, 209497, 209498, 209502, 209503, 209504, 209505, 209506, 209507, 209508, 667616, 670746, 675179, 684772, 685669, 685673, 685848, 685938, 687168, 688280, 688927, 711669, 718902, 719155
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?
cytosine + H2O
uracil + NH3
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treatment of BDIX rat colon cancer cells using the cytosine deaminase/5-fluorocytosine suicide system induces apoptosis, modulation of the proteome, and Hsp90beta phosphorylation, mechanism of the anticancer effect, overview
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?
cytosine + H2O
uracil + NH3
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?
cytosine + H2O
uracil + NH3