A cyclic peptide T analogue with high chemotactic activity

M. Marastoni, S. Salvadori, G. Balboni, V. Scaranari, S. Spisani, E. Reali, AL Giuliani, R. Tomatis

Research output: Contribution to journalArticle

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Abstract

Peptide T is an octapeptide (H-Ala-Ser-Thr-Thr-Thr-Asn-Tyr-Thr-OH) based on a consensus sequence that has been identified in HIV proteins. Two conformationally-restricted analogues of peptide T fragment (H-Thr-Thr-Asn-Tyr-Thr-OH) were synthesized by cyclisation of the N-terminal amino group of Thr to the α- or β-carboxyl moiety of Asp introduced at the C-terminus of the peptide. The cyclo Thr-Thr-Asn-Tyr-Thr-Asp(OH) (Cα) showed high in vitro chemotactic activity, whereas the conformational restriction introduced into Thr-Thr-Asn-Tyr-Thr-Asp-OH was incompatible with the CD4 receptor. The cyclic analogue Cα was more active than its ester and the open-chain reference compound H-Thr-Thr-Asn-Tyr-Thr-Asp-OH. It also proved to be highly resistant to degradation by plasma or brain enzymes.

Original languageEnglish
Pages (from-to)383-389
Number of pages7
JournalEuropean Journal of Medicinal Chemistry
Volume27
Issue number4
DOIs
Publication statusPublished - 1992

Fingerprint

Peptide T
Cyclic Peptides
Human Immunodeficiency Virus Proteins
CD4 Antigens
Peptide Fragments
Cyclization
Consensus Sequence
Brain
Esters
Plasmas
Degradation
Peptides
Enzymes
In Vitro Techniques

Keywords

  • biodegradation
  • chemotactic activity
  • peptide T cyclic analogue

ASJC Scopus subject areas

  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Marastoni, M., Salvadori, S., Balboni, G., Scaranari, V., Spisani, S., Reali, E., ... Tomatis, R. (1992). A cyclic peptide T analogue with high chemotactic activity. European Journal of Medicinal Chemistry, 27(4), 383-389. https://doi.org/10.1016/0223-5234(92)90151-P

A cyclic peptide T analogue with high chemotactic activity. / Marastoni, M.; Salvadori, S.; Balboni, G.; Scaranari, V.; Spisani, S.; Reali, E.; Giuliani, AL; Tomatis, R.

In: European Journal of Medicinal Chemistry, Vol. 27, No. 4, 1992, p. 383-389.

Research output: Contribution to journalArticle

Marastoni, M, Salvadori, S, Balboni, G, Scaranari, V, Spisani, S, Reali, E, Giuliani, AL & Tomatis, R 1992, 'A cyclic peptide T analogue with high chemotactic activity', European Journal of Medicinal Chemistry, vol. 27, no. 4, pp. 383-389. https://doi.org/10.1016/0223-5234(92)90151-P
Marastoni M, Salvadori S, Balboni G, Scaranari V, Spisani S, Reali E et al. A cyclic peptide T analogue with high chemotactic activity. European Journal of Medicinal Chemistry. 1992;27(4):383-389. https://doi.org/10.1016/0223-5234(92)90151-P
Marastoni, M. ; Salvadori, S. ; Balboni, G. ; Scaranari, V. ; Spisani, S. ; Reali, E. ; Giuliani, AL ; Tomatis, R. / A cyclic peptide T analogue with high chemotactic activity. In: European Journal of Medicinal Chemistry. 1992 ; Vol. 27, No. 4. pp. 383-389.
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AU - Giuliani, AL

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