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Literature summary for 3.4.17.11 extracted from

  • Davies, L.C.; Friedlos, F.; Hedley, D.; Martin, J.; Ogilvie, L.M.; Scanlon, I.J.; Springer, C.J.
    Novel fluorinated prodrugs for activation by carboxypeptidase G2 showing good in vivo antitumor activity in gene-directed enzyme prodrug therapy (2005), J. Med. Chem., 48, 5321-5328.
    View publication on PubMed

Application

Application Comment Organism
drug development enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs Pseudomonas sp.
medicine enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs Pseudomonas sp.

Inhibitors

Inhibitors Comment Organism Structure
(4-[bis(2-chloroethyl)amino]-2,3,5,6-tetrafluorobenzoyl)-L-glutamic acid prodrug, competitive inhibition Pseudomonas sp.
(4-[bis(2-iodoethyl)amino]-2,3,5,6-tetrafluorobenzoyl)-L-glutamic acid prodrug, competitive inhibition Pseudomonas sp.

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0011
-
(4-[bis(2-bromoethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
0.0012
-
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
0.0017
-
(4-[bis(2-chloroethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
0.0017
-
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
0.0026
-
(4-[bis(2-chloroethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
0.0028
-
(4-[bis(2-iodoethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
0.0034
-
(2-chloroethyl)-(2-(methylsulfoyloxyethyl)amino)aminobenzyl-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.

Metals/Ions

Metals/Ions Comment Organism Structure
Zn2+ required Pseudomonas sp.

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O Pseudomonas sp. a difluorinated prodrug 4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O Pseudomonas sp. RS16 a difluorinated prodrug 4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O Pseudomonas sp. a difluorinated prodrug 4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O Pseudomonas sp. RS16 a difluorinated prodrug 4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
additional information Pseudomonas sp. enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs, overview ?
-
?
additional information Pseudomonas sp. RS16 enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs, overview ?
-
?

Organism

Organism UniProt Comment Textmining
Pseudomonas sp.
-
gene CPG2
-
Pseudomonas sp. RS16
-
gene CPG2
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2-chloroethyl)-(2-(methylsulfoyloxyethyl)amino)aminobenzyl-L-glutamic acid + H2O a prodrug Pseudomonas sp. (2-chloroethyl)-(2-(methylsulfoyloxyethyl)amino)aminobenzoic acid + L-glutamate
-
?
(4-[bis(2-bromoethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid + H2O a trifluorinated prodrug Pseudomonas sp. 4-[bis(2-bromoethyl)amino]-2,3,5-trifluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O a difluorinated prodrug Pseudomonas sp. 4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O a difluorinated prodrug Pseudomonas sp. RS16 4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-chloroethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid + H2O a trifluorinated prodrug Pseudomonas sp. 4-[bis(2-chloroethyl)amino]-2,3,5-trifluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-chloroethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O a difluorinated prodrug Pseudomonas sp. 4-[bis(2-chloroethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-iodoethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid + H2O a trifluorinated prodrug Pseudomonas sp. 4-[bis(2-iodoethyl)amino]-2,3,5-trifluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O a difluorinated prodrug Pseudomonas sp. 4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid + H2O a difluorinated prodrug Pseudomonas sp. RS16 4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoic acid + L-glutamate
-
?
methotrexate + H2O
-
Pseudomonas sp. 4-[(2,4-diamino-6-(pteridinyl)methyl)-methylamino]-benzoic acid + L-glutamate
-
?
methotrexate + H2O
-
Pseudomonas sp. RS16 4-[(2,4-diamino-6-(pteridinyl)methyl)-methylamino]-benzoic acid + L-glutamate
-
?
additional information enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs, overview Pseudomonas sp. ?
-
?
additional information half-lives of prodrugs and drugs, overview Pseudomonas sp. ?
-
?
additional information enzyme is used in enzyme prodrug therapy to treat human breast cancer, the enzyme catalyzes the activation of the di- and trifluorinated prodrugs, overview Pseudomonas sp. RS16 ?
-
?
additional information half-lives of prodrugs and drugs, overview Pseudomonas sp. RS16 ?
-
?

Synonyms

Synonyms Comment Organism
carboxypeptidase G2
-
Pseudomonas sp.
CPG2
-
Pseudomonas sp.

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
assay at Pseudomonas sp.

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
220
-
(4-[bis(2-iodoethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
583
-
(2-chloroethyl)-(2-(methylsulfoyloxyethyl)amino)aminobenzyl-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
732
-
(4-[bis(2-chloroethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
825
-
(4-[bis(2-bromoethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
827
-
(4-[bis(2-bromoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
1150
-
(4-[bis(2-iodoethyl)amino]-3,5-difluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.
1150
-
(4-[bis(2-chloroethyl)amino]-2,3,5-trifluorobenzoyl)-L-glutamic acid pH 7.3, 37 °C Pseudomonas sp.

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.3
-
assay at Pseudomonas sp.