Irreversible inhibition of dipeptidyl peptidase 8 by dipeptide-derived diaryl phosphonates

Journal of Medicinal Chemistry

Volumn 50, Issue 23, 2007, Pages 5568-5570

  Van Der Veken, Pieter ^a   Soroka, Anna ^a   Brandt, Inger ^a   Chen, Yuan Shou ^b   Maes, Marie Berthe ^a   Lambeir, Anne Marie ^a   Chen, Xin ^b   Haemers, Achiel ^a   Scharpé, Simon ^a   Augustyns, Koen ^a   De Meester, Ingrid ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDIABETIC AGENT; BIS(4 ACETAMIDOPHENYL)PHOSPHONATE; DIPEPTIDE DERIVATIVE; DIPEPTIDYL PEPTIDASE; DIPEPTIDYL PEPTIDASE 8; DIPEPTIDYL PEPTIDASE 8 INHIBITOR; DIPEPTIDYL PEPTIDASE II; DIPEPTIDYL PEPTIDASE IV; DIPEPTIDYL PEPTIDASE IV INHIBITOR; ENZYME INHIBITOR; PHOSPHONIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; SITAGLIPTIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; DIABETES MELLITUS; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; ENZYME SUBSTRATE; EQUILIBRIUM CONSTANT; HUMAN; KINETICS; STRUCTURE ACTIVITY RELATION;

DIPEPTIDASES; DIPEPTIDES; ISOINDOLES; KINETICS; PHOSPHONIC ACIDS; PYRROLIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 36148930961     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701005a     Document Type: Article

References (17)

1. (a) Augustyns, K.; Van der Veken, P.; Senten, K.; Haemers, A. The therapeutic potential of inhibitors of dipeptidyl peptidase IV (DPP IV) and related proline specific dipeptidyl peptidases. Curr. Med. Chem. 2005, 12, 971-998.
2. (b) Van der Veken, P.; Haemers, A.; Augustyns, K. Prolyl peptidases related to dipeptidyl peptidase IV: potential for drug discovery. Curr. Topics Med. Chem. 2007, 7, 621-635.
3. Lambeir, A. M.; Durinx, C.; Scharpé, S.; De Meester, I. Dipeptidyl-peptidase IV from bench to bedside: an update on structural properties, functions and clinical aspects of the enzyme DPP IV. Crit. Rev. Clin. Lab. Sci. 2003, 40, 209-294.
4. Amori, R. E.; Lau, J.; Pittas, A. G. Efficacy and safety of incretin therapy in type II diabetes. Systematic review and meta-analysis. JAMA, J. Am. Med. Assoc. 2007, 298, 194-206.
5. (a) Lankas, G. R.; Leiting, B.; Roy, R. S.; Eiermann, G. J.; Beconi, M. G.; Biftu, T.; Chan, C. C.; Edmondson, S.; Feeney, W. P. et al. Dipeptidyl-peptidase IV inhibition for the treatment of type II diabetes-Potential importance of selectivity over dipeptidyl peptidases 8 and 9. Diabetes 2005, 54, 2988-2994.
6. (b) Lankas, G.; Leiting, B.; Roy, R. S.; Eiermann, G. J.; Biftu, T.; Kim, D.; Ok, H.; Weber, A.; Thornberry, N. A. Inhibition of DPP8/9 results in toxicity of preclinical species: potential importance of selective dipeptidyl peptidase IV inhibition for the treatment of type II diabetes. Diabetes 2004, 53, A2-A2, suppl. 2.
7. (a) Powers, J. C.; Asgian, J. L.; Ekici, O. D.; James, K. E. Irreversible inhibition of serine, cysteine and threonine proteases. Chem. Rev. 2002, 102, 4639-4750.
8. (b) Evans, M. J.; Cravatt, B. F. Mechanism-based profiling of enzyme families. Chem. Rev. 2006, 106,-8, 3279-3301.
9. (a) Jiaang, W. T.; Chen, Y. S.; Hsu, T.; Wu, S. H.; Chien, C. H.; Chang, C. N.; Chang, S. P.; Lee, S. P.; Chen, X. Novel isoindoline compounds for potent and selective inhibition of prolyl dipeptidase 8. Bioorg. Med. Chem. Lett. 2005, 15, 687-791.
10. (b) Lu, I. L.; Lee, S. J.; Tsu, H.; Kao, K. H.; Chien, C. H.; Chang, Y. Y.; Chen, Y. S.; Cheng, J. H.; Chang, C. N.; Chen, T. W.; Chang, S. P.; Chen, X.; Jiaang, W. T. Glutamic acid analogues as potent dipeptidyl peptidase IV and 8 inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 3271-3275.
11. (a) Belyaev, A.; Zhang, X. M.; Augustyns, K.; Lambeir, A. M.; De Meester, I.; Vedernikova, I.; Scharpé, S.; Haemers, A. Structure - activity relationship of diaryl phosphonate esters as potent irreversible dipeptidyl peptidase IV inhibitors. J. Med. Chem. 1999, 42, 1041-1052.
12. (b) Senten, K.; Daniels, L.; Van der Veken, P.; De Meester, I.; Lambeir, A. M.; Scharpé, S.; Haemers, A.; Augustyns, K. Rapid parallel synthesis of dipeptide diphenyl phosphonate esters as inhibitors of dipeptidyl peptidases. J. Comb. Chem. 2003, 5, 336-344.
13. (a) De Meester, I.; Belyaev, A.; Lambeir, A. M.; De Meyer, G. R. Y.; Van Osselaer, N.; Haemers, A.; Scharpé, S. In vivo inhibition of dipeptidyl-peptidase IV by Pro-Pro diphenyl phosphonate (prodipine). Biochem. Pharmacol. 1997, 54, 173-179.
14. (b) Jung, F. J.; Yang, L.; De Meester, I.; Augustyns, K.; Cardell, M.; Hillinger, S.; Vogt, P.; Lardinois, D.; Scharpé, S.; Weder, W.; Korom, S. CD 26/DPP IV-targeted therapy of acute lung rejection in rats. J. Heart Lung Transpl. 2006, 25, 1109-1116.
15. (c) Zhai, W.; Cardell, M.; De Meester, I.; Augustyns, K.; Hillinger, S.; Arni, S.; Jungraithmayr, W.; Scharpé, S.; Weder, W.; Korom, S. Intragraft DPP IV inhibition attenuates post-transplant ischemia/reperfusion injury after prolonged ischemia. J. Heart Lung Transpl. 2007, 26, 174-180.
16. Van der Veken, P.; El Sayed, I.; Joossens, J.; Stevens, C. V.; Augustyns, K.; Haemers, A. Lewis acid catalysed synthesis of N-protected diphenyl 1-aminoalkylphosphonates. Synthesis 2005, 634-638.
17. Efforts to establish the identity of an enzyme we recently purified from bovine testes with DPP9 are currently underway; Dubois, V.; Lambeir, A. M.; Van der Veken, P.; Augustyns, K.; Creemers, J.; Chen, X.; Scharpé, S.; De Meester, I. Purification and characterisation of DPP IV-like enzymes from bovine testes: evidence for identification as natural DPP9-like enzyme. Front. Biosci. Accepted.