Literature summary for 3.4.23.16 extracted from

Specker, E.; Boettcher, J.; Brass, S.; Heine, A.; Lilie, H.; Schoop, A.; Mueller, G.; Griebenow, N.; Klebe, G.
Unexpected novel binding mode of pyrrolidine-based aspartyl protease inhibitors: design, synthesis and crystal structure in complex with HIV protease (2006), ChemMedChem, 1, 106-117.

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Cloned(Commentary)

Cloned (Comment)	Organism
expression in Escherichia coli	Human immunodeficiency virus 1

Crystallization (Commentary)

Crystallization (Comment)	Organism
purified recombinant enzyme free or in complex with inhibitor rac-(2S,4S)-N-[4-([benzenesulfonyl-isobutyl-amino]-methyl)-pyrrolidine-3-ylmethyl]-N-benzyl-2-(2,6-dimethyl-phenoxy)-acetamide, 18°C, 3 M NaCl, 0.1 M BisTris, pH 6.5, cryoprotection by 20% glycerol, X-ray diffraction structure determination and analysis at 1.5-1.85 A resolution	Human immunodeficiency virus 1

Inhibitors

Inhibitors	Comment	Organism	Structure
(3S,4S)-3-((benzyl[(2-bromo-4,5-dimethoxyphenyl)carbonyl]amino)methyl)-4-(([2-(2,4-dichlorophenyl)ethyl](4-phenylbutanoyl)amino)methyl)pyrrolidinium	IC50 is 0.0198 mM, binding structure analysis, modelling	Human immunodeficiency virus 1
(3S,4S)-3-((benzyl[(2-bromo-4,5-dimethoxyphenyl)carbonyl]amino)methyl)-4-(([2-(2,4-dichlorophenyl)ethyl][3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]amino)methyl)pyrrolidinium	IC50 is 0.0221 mM, binding structure analysis, modelling	Human immunodeficiency virus 1
amprenavir	-	Human immunodeficiency virus 1
pyrrolidinemehylene diamine derivatives	binding mode of pyrrolidine-based aspartyl protease inhibitors: design, synthesis and crystal structure in complex with HIV protease, overview	Human immunodeficiency virus 1
rac-(3S,4S)-N-benzyl-2-(2,6-dimethyl-phenoxy)-N-4-[[(isobutyl-(toluene-4-sulfonyl)-amino)-methyl]-pyrrolidin-3-ylmethyl]-acetamide	IC50 is 0.0121 mM, binding structure analysis, modelling	Human immunodeficiency virus 1
rac-(3S,4S)-N-[4-([4-amino-benzenesulfonyl-isobutyl-amino]-methyl)-pyrrolidin-3-ylmethyl]-N-benzyl-2-(2,6-dimethyl-phenoxy)-acetamide	IC50 is 0.0033 mM, binding structure analysis, modelling	Human immunodeficiency virus 1
rac-(3S,4S)-N-[4-([benzenesulfonyl-isobutyl-amino]-methyl)-pyrrolidin-3-ylmethyl]-N-benzyl-2-(2,6-dimethyl-phenoxy)-acetamide	IC50 is 0.0022 mM, binding structure analysis, modelling	Human immunodeficiency virus 1
tipranavir	IC50 is 30 nM, interacts with residues Asp25 and Asp25', and Ile50 and Ile50'	Human immunodeficiency virus 1

Organism

Organism	UniProt	Comment	Textmining
Human immunodeficiency virus 1	-	i.e. HIV-1	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
Abz-Thr-Ile-Nle-4-nitro-Phe-Gln-Arg-NH2 + H2O	the fluorogenic peptide substrate	Human immunodeficiency virus 1	Abz-Thr-Ile-Nle + 4-nitro-Phe-Gln-Arg-NH2	-	?

Subunits

Subunits	Comment	Organism
dimer	-	Human immunodeficiency virus 1

Synonyms

Synonyms	Comment	Organism
HIV-1 protease	-	Human immunodeficiency virus 1

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
5.5	-	assay at	Human immunodeficiency virus 1

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
0.0000006	-	amprenavir	-	Human immunodeficiency virus 1

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
0.00003	-	IC50 is 30 nM, interacts with residues Asp25 and Asp25', and Ile50 and Ile50'	Human immunodeficiency virus 1	tipranavir
0.0022	-	IC50 is 0.0022 mM, binding structure analysis, modelling	Human immunodeficiency virus 1	rac-(3S,4S)-N-[4-([benzenesulfonyl-isobutyl-amino]-methyl)-pyrrolidin-3-ylmethyl]-N-benzyl-2-(2,6-dimethyl-phenoxy)-acetamide
0.0033	-	IC50 is 0.0033 mM, binding structure analysis, modelling	Human immunodeficiency virus 1	rac-(3S,4S)-N-[4-([4-amino-benzenesulfonyl-isobutyl-amino]-methyl)-pyrrolidin-3-ylmethyl]-N-benzyl-2-(2,6-dimethyl-phenoxy)-acetamide
0.0121	-	IC50 is 0.0121 mM, binding structure analysis, modelling	Human immunodeficiency virus 1	rac-(3S,4S)-N-benzyl-2-(2,6-dimethyl-phenoxy)-N-4-[[(isobutyl-(toluene-4-sulfonyl)-amino)-methyl]-pyrrolidin-3-ylmethyl]-acetamide
0.0198	-	IC50 is 0.0198 mM, binding structure analysis, modelling	Human immunodeficiency virus 1	(3S,4S)-3-((benzyl[(2-bromo-4,5-dimethoxyphenyl)carbonyl]amino)methyl)-4-(([2-(2,4-dichlorophenyl)ethyl](4-phenylbutanoyl)amino)methyl)pyrrolidinium
0.0221	-	IC50 is 0.0221 mM, binding structure analysis, modelling	Human immunodeficiency virus 1	(3S,4S)-3-((benzyl[(2-bromo-4,5-dimethoxyphenyl)carbonyl]amino)methyl)-4-(([2-(2,4-dichlorophenyl)ethyl][3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoyl]amino)methyl)pyrrolidinium

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Release 2023.1 (January 2023)