Synthesis and evaluation of Glyψ(PO2R-N)pro-containing pseudopeptides as novel inhibitors of the human cyclophilin hCyp-18

Journal of Medicinal Chemistry

Volumn 45, Issue 18, 2002, Pages 3928-3933

  Demange, Luc ^a   Moutiez, Mireille ^a   Dugave, Christophe ^a  

^a CEA SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLALANYL (2 OXO 3 AMINOPROPANOYL)PROLYL 1 (4 NITROPHENYL)AMINO 2 BENZYL 2 AMINOETHANE; ACETYLALANYLAMINOMETHYLPHOSPHONYLPROLYLPHENYLALANYL 4 CARBOXYMETHYLANILINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CYCLOPHILIN; CYCLOPHILIN INHIBITOR; FK 506 BINDING PROTEIN; PSEUDOPEPTIDE; SUCCINYLALANYLETHYLAMINOMETHYLPHOSPHONYLPROLYLPHENYLALANYL 4 NITROANILINE; UNCLASSIFIED DRUG; AMIDE; CYCLOPHILIN HCYP 18; CYCLOPHILIN HCYP-18; ENZYME INHIBITOR; OLIGOPEPTIDE; PHOSPHONIC ACID DERIVATIVE; SUCCINYL ALANYL GLYCYL PSEUDO(PO2ET N)PROLYL PHENYLALANINE 4 NITROANILINE; SUCCINYL-ALANYL-GLYCYL-PSEUDO(PO2ET-N)PROLYL-PHENYLALANINE-4-NITROANILINE;

ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROGEN BOND; MEDICAL LITERATURE; PROTEIN FOLDING; PROTEIN MOTIF; CHEMISTRY; DRUG ANTAGONISM; MOLECULAR MIMICRY; SYNTHESIS;

AMIDES; CYCLOPHILINS; ENZYME INHIBITORS; HUMANS; MOLECULAR MIMICRY; OLIGOPEPTIDES; PHOSPHONIC ACIDS;

EID: 0037194543     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020865i     Document Type: Article

References (42)

1. Peptidyl-prolyl cis-trans isomerases
2. Sequence-specific and phosphorylation-dependent proline isomerization: A potential mitotic regulatory mechanism
3. Peptidyl prolyl cis-trans isomerase activity of cyclophilin A in functional homo-oligomeric receptor expression
4. Immunophilins: Beyond immunosuppression
5. Absconding with the chaperone: Essential Cyclophilin-Gag interaction in HIV-1 virions
6. Maturation-induced conformational changes of HIV-1 capsid protein and identification of two high affinity sites for cyclophilins in the C-terminal domain
7. Cyclophilin A regulates HIV-1 infectivity, as demonstrated by gene targeting in human T-cells
8. Crystal structure of cyclophilin A complexed with substrate Ala-Pro suggests a solvent-assisted mechanism of cis-trans isomerization
9. Inhibition of human immunodeficiency virus replication by nonimmunosuppressive analogs of cyclosporin A
10. Mode of action of SDZ.NIM 811, a nonimmunosuppressive cyclosporin A analog with activity against human immunodeficiency virus type I (HIV-1): Interference with early and late events in HIV-1 replication
11. Mode of action of SDZ NIM 811, a nonimmunosuppressive cyclosporin A analog with activity against human immunodeficiency virus (HIV) type 1: Interference with HIV protein-Cyclophilin A interactions
12. Design of a Gag-pentapeptide analog which binds the human cyclophilin A more efficiently than the entire capsid protein: New insights for the development of novel anti HIV-1 drugs
13. Inhibition of peptidylprolyl cis/trans isomerase activity by substrate analog structures: Thioxo tetrapeptide-4-nitroanilides
14. Cyclophilin inhibition by a (Z)-alkene cis-proline mimic
15. Structure-activity studies of ground- and transition-state analog inhibitors of cyclophilin
16. Binding energy and catalysis: The implication for transition-state analogs and catalytic antibodies
17. Crystal structure implies that Cyclophilin predominantly catalyzes the trans to cis isomerization
18. Peptidyl-prolyl cis/trans isomerases and their effectors
19. Inhibition of FKBP rotamase activity by immunosuppressant FK506: Twisted amide surrogate
20. Intramolecular assistance of cis/trans isomerization of the histidine-proline moiety
21. Mechanistic studies of peptidyl prolyl cis-trans isomerase: Evidence for catalysis by distortion
22. Mechanistic studies of enzymic and nonenzymic prolyl cis-trans isomerization
23. a hydrogen bond in prolyl peptides
24. Catalytic antibodies with peptidylprolyl cis-trans isomerase activity
25. Antibody catalysis of peptidyl-prolyl cis-trans isomerization in the folding of RNase T1
26. Neuroimmunophilin ligands and novel therapeutics for the treatment of degenerative disorders of the nervous system
27. A human peptidyl-prolyl isomerase essential for regulation of mitosis
28. The prolyl isomerase Pin1 restores the function of Alzheimer-associated phosphorylated tau protein
29. Structural and functional analysis of the mitotic rotamase Pinl suggests substrate recognition is phosphorylation dependent
30. 2R-CH)Pro as potential inhibitors of the human cyclophilin hCyp-18
31. Design and therapeutic application of matrix metalloproteinase inhibitors
32. A theoretical investigation of phosphonamidates and sulfonamides as protease transition-state isosteres
33. Human and Escherichia coli Cyclophilins: Sensitivity to inhibition by the immunosuppressant cyclosporin A correlates with a specific tryptophan residue
34. A protease-free assay for peptidyl prolyl cis/trans isomerases using standard peptide substrates
35. Mapping the stereospecificity of peptidyl prolyl cis/trans isomerases
36. Determination of kinetic constants for peptidylprolyl cistrans isomerases by an improved spectrophotometric assay
37. Interaction of the human cyclophilin hCyp-18 with short peptides suggests the existence of two functionally independent subsites
38. Prolyl isomerases do not catalyze isomerization of non-prolyl peptide bonds
39. Phosphonamidates and phosphonamidate esters as HIV-1 protease inhibitors
40. Peptides containing aminophosphonic acids. II. The synthesis of tripeptide analogs
41. Synthesis and biological evaluation of phosphonamidate peptide inhibitors of enkephalinase and angiotensin-converting enzyme
42. Side-chain effects on peptidyl-prolyl cis/trans isomerization