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Chemical Compound Review

AR-1J3302     (2S)-2-[[(2S)-2-[[(2S)-4- aminocarbonyl-2...

Synonyms: AC1L2QI6, Lvv-hemorphin-7, Leu-val-val-tyr-pro-trp-thr-gln-arg-phe
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Disease relevance of Leu-val-val-tyr-pro-trp-thr-gln-arg-phe


Psychiatry related information on Leu-val-val-tyr-pro-trp-thr-gln-arg-phe


High impact information on Leu-val-val-tyr-pro-trp-thr-gln-arg-phe

  • The current finding suggests that LVV-hemorphin-7 is a functional peptide in the central nervous system and in view of its abundance in neural tissue, compared with angiotensin IV, may be of significant physiological importance [1].
  • Recently, we found that LVV-hemorphin-7, a fragment of beta globin, is an abundant peptide in the brain and binds to the AT4 receptor with high affinity and specificity [1].
  • A globin fragment, LVV-hemorphin-7, induces [3H]thymidine incorporation in a neuronal cell line via the AT4 receptor [1].
  • This peptide is identical to the amino acid sequence 30-39 of sheep betaA- and betaB-globins and has previously been named LVV-hemorphin-7 [4].
  • Binding was displaced with high potency by the "AT4 receptor" ligands (Ang IV > divalinal1-Ang IV approximately LVV-hemorphin-7 approximately LVV-hemorphin-6 > Ang (3-7) > Ang III > Ang (4-8)) but not by AT1/AT2 receptor antagonists [5].

Biological context of Leu-val-val-tyr-pro-trp-thr-gln-arg-phe


Anatomical context of Leu-val-val-tyr-pro-trp-thr-gln-arg-phe


Associations of Leu-val-val-tyr-pro-trp-thr-gln-arg-phe with other chemical compounds

  • 1. The human orphan G-protein coupled receptor bombesin receptor subtype 3 (hBRS-3) was screened for peptide ligands by a Ca(2+)mobilization assay resulting in the purification and identification of two specific ligands, the naturally occurring VV-hemorphin-7 (VV-H-7) and LVV-hemorphin-7 (LVV-H-7), from human placental tissue [13].
  • All LVV-hemorphin-7 analogs tested, except for Leu-Val-Val-Tyr, inhibit the cleavage of the synthetic substrate, leucine beta-naphthylamide, by IRAP, with K(i) values between 56 and 620 nM [14].

Gene context of Leu-val-val-tyr-pro-trp-thr-gln-arg-phe

  • We find that the Val(3) residue is crucial for LVV-hemorphin-7 binding to IRAP, whereas the C-terminal domain seems to play a minor role [14].
  • Their primary structure and accurate molecular weights, determined by amino acid analysis and fast atom bombardment (FAB) mass spectrometry, were identical to fragments 31-40 (LVV-hemorphin-7) and 32-40 (VV-hemorphin 7) of the beta-chain of bovine hemoglobin [15].
  • Our results indicate that VV-hemorphin-7 and LVV-hemorphin-7 exhibit a lesser potency both in GPI and binding tests [16].

Analytical, diagnostic and therapeutic context of Leu-val-val-tyr-pro-trp-thr-gln-arg-phe


  1. A globin fragment, LVV-hemorphin-7, induces [3H]thymidine incorporation in a neuronal cell line via the AT4 receptor. Moeller, I., Albiston, A.L., Lew, R.A., Mendelsohn, F.A., Chai, S.Y. J. Neurochem. (1999) [Pubmed]
  2. Isolation of the opioid peptide Leu-Val-Val-hemorphin-7 from bronchoalveolar lavage fluid of a patient with non-small cell lung cancer. Duethman, D., Dewan, N., Conlon, J.M. Peptides (2000) [Pubmed]
  3. The angiotensin IV/AT4 receptor. Chai, S.Y., Fernando, R., Peck, G., Ye, S.Y., Mendelsohn, F.A., Jenkins, T.A., Albiston, A.L. Cell. Mol. Life Sci. (2004) [Pubmed]
  4. The globin fragment LVV-hemorphin-7 is an endogenous ligand for the AT4 receptor in the brain. Moeller, I., Lew, R.A., Mendelsohn, F.A., Smith, A.I., Brennan, M.E., Tetaz, T.J., Chai, S.Y. J. Neurochem. (1997) [Pubmed]
  5. Endogenous cystinyl aminopeptidase in Chinese hamster ovary cells: characterization by [125I]Ang IV binding and catalytic activity. Demaegdt, H., Vanderheyden, P., De Backer, J.P., Mosselmans, S., Laeremans, H., Le, M.T., Kersemans, V., Michotte, Y., Vauquelin, G. Biochem. Pharmacol. (2004) [Pubmed]
  6. Hemorphin and hemorphin-like peptides isolated from dog pancreas and sheep brain are able to potentiate bradykinin activity in vivo. Ianzer, D., Konno, K., Xavier, C.H., St??cklin, R., Santos, R.A., de Camargo, A.C., Pimenta, D.C. Peptides (2006) [Pubmed]
  7. Kinetic of in vitro generation of some hemorphins: early release of LVV-hemorphin-7, precursor of VV-hemorphin-7. Dagouassat, N., Garreau, I., Zhao, Q., Sannier, F., Piot, J.M. Neuropeptides (1996) [Pubmed]
  8. Renal hemodynamic responses to intrarenal infusion of ligands for the putative angiotensin IV receptor in anesthetized rats. Fitzgerald, S.M., Evans, R.G., Bergström, G., Anderson, W.P. J. Cardiovasc. Pharmacol. (1999) [Pubmed]
  9. Potentiation of cholinergic transmission in the rat hippocampus by angiotensin IV and LVV-hemorphin-7. Lee, J., Chai, S.Y., Mendelsohn, F.A., Morris, M.J., Allen, A.M. Neuropharmacology (2001) [Pubmed]
  10. Rapid analysis of endogenous LVV-hemorphin-7 in cerebrospinal fluid by size-exclusion chromatography and electrospray ionization mass spectrometry. Silberring, J., Nyberg, F. Journal of chromatography. A. (1997) [Pubmed]
  11. Brain processing of hemorphin-7 peptides in various subcellular fractions from rats. Murillo, L., Piot, J.M., Coitoux, C., Fruitier-Arnaudin, I. Peptides (2006) [Pubmed]
  12. In vitro metabolism of LVV-Hemorphin-7 by renal cytosol and purified prolyl endopeptidase. Fruitier-Arnaudin, I., Cohen, M., Coitoux, C., Piot, J.M. Peptides (2003) [Pubmed]
  13. Identification and functional characterization of hemorphins VV-H-7 and LVV-H-7 as low-affinity agonists for the orphan bombesin receptor subtype 3. Lammerich, H.P., Busmann, A., Kutzleb, C., Wendland, M., Seiler, P., Berger, C., Eickelmann, P., Meyer, M., Forssmann, W.G., Maronde, E. Br. J. Pharmacol. (2003) [Pubmed]
  14. Structure-activity study of LVV-hemorphin-7: angiotensin AT4 receptor ligand and inhibitor of insulin-regulated aminopeptidase. Lee, J., Mustafa, T., McDowall, S.G., Mendelsohn, F.A., Brennan, M., Lew, R.A., Albiston, A.L., Chai, S.Y. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  15. Isolation and characterization of two opioid peptides from a bovine hemoglobin peptic hydrolysate. Piot, J.M., Zhao, Q., Guillochon, D., Ricart, G., Thomas, D. Biochem. Biophys. Res. Commun. (1992) [Pubmed]
  16. VV-hemorphin-7 and LVV-hemorphin-7 released during in vitro peptic hemoglobin hydrolysis are morphinomimetic peptides. Garreau, I., Zhao, Q., Pejoan, C., Cupo, A., Piot, J.M. Neuropeptides (1995) [Pubmed]
  17. In vitro metabolism of LVV-hemorphin-7 in human plasma studied by reversed-phase high-performance liquid chromatography and micro-electrospray mass spectrometry. Sanderson, K., Andrén, P.E., Caprioli, R.M., Nyberg, F. Journal of chromatography. A. (1996) [Pubmed]
  18. In vivo processing of LVV-hemorphin-7 in rat brain and blood utilizing microdialysis combined with electrospray mass spectrometry. Nydahl, K.S., Pierson, J., Nyberg, F., Caprioli, R.M., Andrén, P.E. Rapid Commun. Mass Spectrom. (2003) [Pubmed]
  19. Opioid peptides derived from hemoglobin: hemorphins. Zhao, Q., Garreau, I., Sannier, F., Piot, J.M. Biopolymers (1997) [Pubmed]
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