Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 5, 2005, Pages 1493-1496

  Araya, Eyleen ^a   Rodriguez, Alex ^b   Rubio, Jaime ^b   Spada, Alessandro ^a   Joglar, Jesus ^a   Llebaria, Amadeu ^a   Lagunas, Carmen ^d   Fernandez, Andres G ^d   Spisani, Susanna ^e   Perez, Juan J ^c  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c UNIVERSITAT POLITÈCNICA DE CATALUNYA   (Spain)

^d Laboratorios Salvat SA   (Spain)

^e UNIVERSITY OF FERRARA   (Italy)

Author keywords

Amygdalin derivatives; Peptidomimetics; Psoriasis

Indexed keywords

AMYGDALIN; AMYGDALIN DERIVATIVE; CHEMOTACTIC PEPTIDE; FUNCTIONAL GROUP; PEPTIDE T; UNCLASSIFIED DRUG;

ARTICLE; CHEMOTAXIS; CONCENTRATION RESPONSE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; MONOCYTE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 13944252004     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.12.071     Document Type: Article

References (14)

1. C.B. Pert, J.M. Hill, M.R. Ruff, R.M. Bernan, W.G. Robey, L.O. Arthur, F.W. Ruscetti, and W.L. Farrar Octapeptides deduced from the neuropeptide receptor-like pattern of antigen T4 in brain potently inhibit human immunodeficiency virus receptor binding and T-cell infectivity Proc. Natl. Acad. Sci. U.S.A. 83 1986 9254 9258
2. M.R. Ruff, B.M. Martin, E.I. Ginns, W.L. Farrar, and C.B. Pert CD4 receptor binding peptides that block HIV infectivity cause human monocyte chemotaxis. Relationship to vasoactive intestinal polypeptide FEBS Lett. 211 1987 17 22
3. L. Wetterberg, B. Alexius, J. Saaf, A. Sonnenberg, S. Britton, and C.B. Pert Peptide T in treatment of AIDS Lancet 1 1987 159
4. E.M. Farber, E.N. Cohen, D.J. Trozak, and D.I. Wilkinson Peptide T improves psoriasis when infused into lesions in nanogram amounts J. Am. Acad. Dermatol. 25 1991 658 664
5. S.K. Raychaudhuri, S.P. Raychaudhuri, and E.M. Farber Anti-chemotactic activities of peptide-T: a possible mechanism of actions for its therapeutic effects on psoriasis Int. J. Immunopharmacol. 20 1998 661 667
6. M.A. Tufano, R. Greco, I. Paoletti, G. Donnarumma, N. Canozo, and A. Baroni Immunomodulatory effects of peptide T on human keratinocyte cells Br. J. Dermatol. 147 2002 663 669
7. M. Marastoni, S. Salvadori, G. Baloni, V. Scaranari, S. Spisani, E. Reali, S. Traniello, and R. Tomatis Structure-activity relationships of cyclic and linear peptide T analogues Int. J. Pept. Protein Res. 41 1993 441 454
8. N.B. Centeno, and J.J. Perez A proposed bioactive conformation of peptide T J. Compd.-Aided Mol. Design. 12 1998 7 14
9. O. Llorens, N.B. Centeno, M. Filizola, S. Spisani, M. Marastoni, M. Calafell, C. Herranz, and J.J. Perez A proposed bioactive form of peptide T and the design of peptidomimetics Lett. Pept. Sci. 5 1998 179 182
10. O. Llorens, M. Filizola, S. Spisani, M. Marastoni, C. Herranz, and J.J. Perez Amygdalin binds to the CD4 receptor as suggested from molecular modeling studies Bioorg. Med. Chem. Lett. 8 1998 781 786
11. M. Holzbecher, M. Moss, and H. Ellenberger The cyanide content of Laetrile preparations, apricot, peach and apple seeds Clin. Toxicol. 22 1984 341 347
12. T. Ziegler, and U. Seidl Preparation of some amygdalin-derived gentiobiosyl donors and acceptors for oligosacchacaride synthesis J Carbohydr. Chem. 10 1991 813 831
13. C. Bliard, G. Massiot, and S. Nazabadioko Amygdalin as building block in oligosaccharide synthesis Tetrahedron Lett. 34 1993 5083 5084
14. The R enantiomer of this product was previously described in: T. Hirata, and K. Shimoda Bull. Chem. Jpn. 74 2001 539 542