Metal polypeptides
AssigneeInstitut National de la Sante et de la Recherche Medicale
InventorsJean-Francois Bach, Mireille Dardenne, Jean-Marie Pleau, Jean Hamburger, Evangheios Bricas, Jean Martinez, Didier Blanot, Genevieve Auger, Pierre Lefrancier, Bernard Amor
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Abstract
The present invention relates to novel peptide compounds, of which the chemical structure is related to that of the polypeptide hormone having a thymic activity, isolated from the blood serum of pig, and the application of these novel compounds for therapeutic purposes. This invention also relates to intermediates useful in preparing the active compounds of the invention.
Claims47
A process for the preparation of a new product from a starting material selected from the serum thymic factor and its analogs and derivatives, which comprises reacting said starting material with a reactant containing metal ions or a metal-containing protein substance, said metal being capable of forming a IV co-ordination complex having a tetrahedral phase.
A complex of serum thymic factor and its analogs and derivatives with a metal, or a metal-containing protein substance which is capable of forming a IV coordination complex having a tetrahedral configuration.
A process for preparing a peptide containing composition suitable for use in the treatment of an unbalance of T lymphocytes in a host which comprises contacting a thymic extract or a serum thymic factor containing a nonapeptide of the sequence:
- pGlu-Ala-Lys-Ser-Gln-Gly-Ser-Asn
- with a reactant selected from the group consisting of metal, metal salts and metal-containing protein substances, said metal being capable of forming a IV co-ordination complex having a tetrahedral shape.
The process of claim 44 wherein the reactant is a zinc salt.
A complex of a metal capable of forming a IV co-ordination complex having a tetrahedral shape and a peptide selected from the group consisting of
- Gln-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-D-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asp
- PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ala-Asn
- PyroGlu-Ala-Lys-Ala-Gln-Gly-Gly-Ser-Asn
- Z Gln-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-D-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Lys(n.sup.6 -Acetyl)-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Orn-Ser-Gln-Gly-Gly-Ser-Asn
- PryoGlu-Ala-Lys-D-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Lys-Ser-D-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-lys-Ser-Gln-Gly-Gly-Ser-Gln
- PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser-B-Ala-NH.sub.2
- PyroGlu-Ala-Lys-Ser-Gln-D-Ala(Gly-ser-Asn)
- PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser-D-Asn
- PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn-NH.sub.2
- PyroGlu-Ala-Lys-Ser-Asn-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Lys-Ser-Nva-Gly-Gly-Ser-Asn
- D-PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- D-Gln-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- Pro-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Arg-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Har-Ser-Gln-Gly-Gly-Ser-Asn and
- PyroGlu-Ala-Lys-(N.sup.6 -acetyl)-Ser-Gln-D-Ala-Gly-Ser-Asn.
A complex of a metal capable of forming a IV co-ordination complex having a tetrahedral shape and a peptide selected from the group consisting of
- Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser
- D-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- PyroGlu-Ala-Lys-(N-methyl)Ser-Gln-Gly-Ser-Asn
- PyroGlu-Ala-(2, 6-diaminohexynol)-Ser-Gly-gly-gly-Ser-Asn and
- PyroGlu-Ala-Hep-Ser-Gln-Gly-gly O Ser-Asn.
a complex of a metal capable of forming a IV co-ordination complex having a tetrahedral shape and a peptide selected from the group consisting of
- Lys(N.sup.6 acetyl)-Ser-Gln-Gly-Ser-Asn
- D-Lys-Ser-Gln-Gly-Gly-Ser-Asn
- Orn-Ser-Gon-Gly-Gly-Ser-Asn
- Na Z.Lys-Ser-Gln-gly-Gly-Ser-Asn
- Lys-Ser-Gln-D-Ala-Gly-Ser-Asn
- Z-Ala-Lys-Ser-Gln-Gly-Ser-Asn and
- Lys-Ser-Gln-Gly-Gly-Ser-Asn.
A complex of a metal capable of forming a IV co-ordination complex having a tetrahedral shape and a peptide having the amino acid sequence
- Ser-Gln-Gly-Gly-Ser-Asn.
A polypeptide having the sequence X-Gln-Gly-Gly-Y wherein Y is -Ser-Asn and X is Lys-Ser, Ala-Lys-Ser or Glx-Ala-Lys-Ser- wherein Glx is PyroGlu or Gln;
- and when X is Glx-Ala-Lys-Ser, Y can also be -Ser;
- and said polypeptide in which one or two amino acids in said sequence are replaced as follows:
- a. Ser.sup.4 or Ser.sup.8 is replaced by:
- Thr, Ala or N-methyl-Ser;
- PyroGlu is replaced by Pro;
- c. Lys.sup.3 is replaced by:
- (N.sup.6 -acetyl)-Lys, 2-aminohexanoyl, 2-6-diaminohexynoyl, Arg, Har or Orn.;
- d. Gln.sup.5 is replaced by:
- Glu, Met(0), Asn or Nor-Val;
- e. Gly.sup.6 or Gly.sup.7 either one individually, is replaced by:
- Ala, Sar or Leu, and Asn-NH.sub.2, and the polypeptides, PyroGlu-Ala-Lys-Ser-Gln-Gly-Gly-Gly-Ser-Asn, and PyroGlu-Ala-Lys-Ser-Gln-Gly-Ser-Asn, with the proviso that the unmodified polypeptides PyroGlu-Ala-Lys-Ser-Gln-Gly-Ser-Asn and Gln-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn are not included.
Dependencies are inferred from the claim text.