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Chemical Compound Review

Ile-Pro-Ile     (2S,3S)-2-[[(2S)-1-[(2S,3S)- 2-amino-3...

Synonyms: diprotin A, CHEMBL214381, AG-J-89383, SureCN6404766, BSPBio_003515, ...
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High impact information on diprotin A

  • Conversion to GRH(3-44)-NH2 was blocked by diprotin A, a DPP type IV (DPP IV) competitive inhibitor [1].
  • Treatment of transduced bone marrow cells with Diprotin A permitted long-term expression of a retrovirally encoded MHC class I gene on multiple hematopoietic cell lineages after transplantation of a suboptimal number of transduced cells [2].
  • These products were significantly reduced when the specific DPP IV inhibitor diprotin A was included in the incubation mixture and were absent when serum from DPP IV-deficient rats was used [3].
  • Enalaprilat (an inhibitor of kininase II) blocked the formation of BK1-7 and BK1-5 and increased the recovery of BK4-9. beta-Mercapto-ethanol, which inhibits aminopeptidase P, and diprotin A, a specific inhibitor of dipeptidylaminopeptidase IV, both reduced the formation of BK4-9 [4].
  • One of them cleaves the prolyl bond in the synthetic dipeptide nitroanilide Gly-Pro-pNA (Km 0.95 mM and Vmax 8 nmol/h at pH 7.4 and 37 degrees C) and is specifically inhibited by phenylmethane sulfonyl fluoride, diprotin A, Gly-Pro-Ala and Gly-Pro-Gly-Gly [5].

Biological context of diprotin A


Anatomical context of diprotin A

  • Here, we demonstrate that treatment of retrovirally transduced mouse bone marrow cells with the tri-peptide Diprotin A (Ile-Pro-Ile), a specific inhibitor of CD26, significantly enhances engraftment of retrovirally transduced HSCs [2].
  • In vitro permeation studies revealed that the permeability coefficient of ENI across porcine buccal epithelium was 5.67+/-4.74x10(-7) cm/s. The enzymatic degradation of ENI was found not to be rate limiting to the drug's permeation across buccal epithelium, as diprotin-A did not increase the permeation of ENI [11].
  • The dipeptidyl aminopeptidase IV (DP IV) inhibitor Diprotin A produces a full, dose-dependent, short-lasting and naloxone-reversible analgesia in the rat tail-flick test when given intracerebroventricularly, with an ED50 of 295 nmol/rat but it has no direct opioid agonist activity in the longitudinal muscle strip of guinea-pig ileum bioassay [12].
  • In this study, we determined cell growth, insulin content, insulin accumulation and insulin secretory function of a insulin-secreting cell line cultured for 3 days with either GLP-1, GLP-1 plus the DPP IV inhibitor diprotin A (DPA) or stable N-acetyl-GLP-1 [13].

Associations of diprotin A with other chemical compounds


Gene context of diprotin A

  • In this paper, we discuss the molecular interaction mechanism of diprotin A with hDPPIV based on the X-ray crystal structure [8].
  • The DPIV-like activity was specifically inhibited by both Diprotin A and B, non-competitively, generating a K(i) of 1.4 x 10(-4) M for both inhibitors [19].
  • The recombinant DPP IV showed a high affinity for the synthetic peptide glycine-proline-p-nitroanilide and was strongly inhibited by Hg2+ and diprotin A [20].
  • 5. Diprotin A (Ile-Pro-Ile) was an efficient competitive inhibitor of the cockroach DPP, whereas other known DPP inhibitors were found to be less potent [21].
  • The formation of GIP(3-42) was almost completely abolished by inhibition of plasma DPP IV with diprotin A [22].

Analytical, diagnostic and therapeutic context of diprotin A


  1. Dipeptidylpeptidase IV and trypsin-like enzymatic degradation of human growth hormone-releasing hormone in plasma. Frohman, L.A., Downs, T.R., Heimer, E.P., Felix, A.M. J. Clin. Invest. (1989) [Pubmed]
  2. Inhibition of CD26 peptidase activity significantly improves engraftment of retrovirally transduced hematopoietic progenitors. Tian, C., Bagley, J., Forman, D., Iacomini, J. Gene Ther. (2006) [Pubmed]
  3. Degradation of glucose-dependent insulinotropic polypeptide and truncated glucagon-like peptide 1 in vitro and in vivo by dipeptidyl peptidase IV. Kieffer, T.J., McIntosh, C.H., Pederson, R.A. Endocrinology (1995) [Pubmed]
  4. Bradykinin metabolism pathway in the rat pulmonary circulation. Pesquero, J.B., Jubilut, G.N., Lindsey, C.J., Paiva, A.C. J. Hypertens. (1992) [Pubmed]
  5. Murine thymocytes possess specific cell surface-associated exoaminopeptidase activities: preferential expression by immature CD4-CD8- subpopulation. Bauvois, B. Eur. J. Immunol. (1990) [Pubmed]
  6. Substance P and neurokinin A metabolism by cultured human skeletal muscle myocytes and fibroblasts. Russell, J.S., Chi, H., Lantry, L.E., Stephens, R.E., Ward, P.E. Peptides (1996) [Pubmed]
  7. The role of substance P and bradykinin in the cough reflex and bronchoconstriction in guinea-pigs. El-Hashim, A.Z., Amine, S.A. Eur. J. Pharmacol. (2005) [Pubmed]
  8. The crystal structure of human dipeptidyl peptidase IV (DPPIV) complex with diprotin A. Hiramatsu, H., Yamamoto, A., Kyono, K., Higashiyama, Y., Fukushima, C., Shima, H., Sugiyama, S., Inaka, K., Shimizu, R. Biol. Chem. (2004) [Pubmed]
  9. SDF-1/CXCL12 enhances survival and chemotaxis of murine embryonic stem cells and production of primitive and definitive hematopoietic progenitor cells. Guo, Y., Hangoc, G., Bian, H., Pelus, L.M., Broxmeyer, H.E. Stem Cells (2005) [Pubmed]
  10. Structural basis of proline-specific exopeptidase activity as observed in human dipeptidyl peptidase-IV. Thoma, R., Löffler, B., Stihle, M., Huber, W., Ruf, A., Hennig, M. Structure (Camb.) (2003) [Pubmed]
  11. Transbuccal peptide delivery: stability and in vitro permeation studies on endomorphin-1. Bird, A.P., Faltinek, J.R., Shojaei, A.H. Journal of controlled release : official journal of the Controlled Release Society. (2001) [Pubmed]
  12. Diprotin A, an inhibitor of dipeptidyl aminopeptidase IV(EC produces naloxone-reversible analgesia in rats. Rónai, A.Z., Timár, J., Makó, E., Erdö, F., Gyarmati, Z., Tóth, G., Orosz, G., Fürst, S., Székely, J.I. Life Sci. (1999) [Pubmed]
  13. Function of a long-term, GLP-1-treated, insulin-secreting cell line is improved by preventing DPP IV-mediated degradation of GLP-1. Green, B.D., Liu, H.K., McCluskey, J.T., Duffy, N.A., O'Harte, F.P., McClenaghan, N.H., Flatt, P.R. Diabetes, obesity & metabolism. (2005) [Pubmed]
  14. Increase of CD26/dipeptidyl peptidase IV expression on human gingival fibroblasts upon stimulation with cytokines and bacterial components. Nemoto, E., Sugawara, S., Takada, H., Shoji, S., Horiuch, H. Infect. Immun. (1999) [Pubmed]
  15. Characterization of specific proteases associated with the surface of human skin fibroblasts, and their modulation in pathology. Raynaud, F., Bauvois, B., Gerbaud, P., Evain-Brion, D. J. Cell. Physiol. (1992) [Pubmed]
  16. The effects of endomorphins and diprotin A on striatal dopamine release induced by electrical stimulation-An in vitro superfusion study in rats. Bagosi, Z., J??szber??nyi, M., Bujdos??, E., Szab??, G., Telegdy, G. Neurochem. Int. (2006) [Pubmed]
  17. Obligatory involvement of CD26/dipeptidyl peptidase IV in the activation of the antiretroviral tripeptide glycylprolylglycinamide (GPG-NH(2)). Balzarini, J., Andersson, E., Schols, D., Proost, P., Van Damme, J., Svennerholm, B., Horal, P., Vahlne, A. Int. J. Biochem. Cell Biol. (2004) [Pubmed]
  18. The inflammatory reaction induced by formalin in the rat paw. Damas, J., Liégeois, J.F. Naunyn Schmiedebergs Arch. Pharmacol. (1999) [Pubmed]
  19. The purification and characterisation of novel dipeptidyl peptidase IV-like activity from bovine serum. Buckley, S.J., Collins, P.J., O'Connor, B.F. Int. J. Biochem. Cell Biol. (2004) [Pubmed]
  20. Cloning, purification, and enzymatic properties of dipeptidyl peptidase IV from the swine pathogen Streptococcus suis. Jobin, M.C., Martinez, G., Motard, J., Gottschalk, M., Grenier, D. J. Bacteriol. (2005) [Pubmed]
  21. Proline-specific dipeptidyl peptidase activity in the cockroach brain and intestine: partial characterization, distribution, and inactivation of tachykinin-related peptides. Nässel, D.R., Mentlein, R., Bollner, T., Karlsson, A. J. Comp. Neurol. (2000) [Pubmed]
  22. Improved glycaemic control in obese diabetic ob/ob mice using N-terminally modified gastric inhibitory polypeptide. O'Harte, F.P., Mooney, M.H., Kelly, C.M., Flatt, P.R. J. Endocrinol. (2000) [Pubmed]
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