Peptidomimetics possessing photo-controlled biological activity
AssigneesKarlsruher Institut für Technologie, National Taras Shevchenko University of Kyiv
InventorsSergiy Afonin, Oleg Babil, Igor Komarov, Pavlo Mykhailiuk, Anne Ulrich
Life of this patent
Estimating the term…
Abstract
The present invention relates to pharmaceutically and/or diagnostically active compounds, in particular peptide analogues (peptidomimetics), which can be reversibly controlled between an active and an inactive state by irradiation with light of different wavelengths. The present invention further relates to an intermediate compound usable in the manufacture of such pharmaceutically and/or diagnostically active compounds, as well as a manufacturing method thereof.
Claims19
A peptidomimetic compound represented by the general formula Ia or a salt thereof,
- wherein
- R1 and R4 are independently selected from the group consisting of H, an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
- R2 and R3 are independently selected from the group consisting of an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
- X represents —(CHxFy)z—, wherein x+y=2, x=0, 1 or 2, y=0, 1 or 2 and z=2 to 4;
- Y1 and Y2 are independently selected from S, SO2, N, N-alkyl, or 0;
- P1 and P3 each independently represents a single amino acid residue or a peptide sequence of 2 or more amino acid residues;
- P2 is absent or represents a single amino acid residue or a peptide sequence of 2 or more amino acid residues;
- Q is C or N;
- R5 is selected from H, an alkyl group, heteroalkyl group, alkenyl group, heteroalkenyl group, alkynyl group or a heteroalkynyl group, and is bound to Q or may form a ring together with Q and N, or R5 is absent;
- R6 is selected from H, an alkyl group, heteroalkyl group, alkenyl group, heteroalkenyl group, alkynyl group, heteroalkynyl group, alkoxy group, aryl group, and heteroaryl group, or is absent;
- and
- R7 is selected from H, a natural amino acid side chain, an alkyl group, heteroalkyl group, alkenyl group, heteroalkenyl group, alkynyl group, heteroalkynyl group, alkoxy group, aryl group or a heteroaryl group;
- with the proviso that when P2 is absent, P1 and P3 are not bonded to each other;
- with the proviso that when Q is N, R5 is absent, and
- with the proviso that when R5 forms a ring together with Q and N, R6 is absent.
Use of a photo-switchable molecular system represented by the following scheme including general formulae IVa and IVb, as a fragment in a pharmaceutically and/or diagnostically active compound, which allows to toggle between an activated and deactivated state thereof
- wherein
- R1 and R4 are independently selected from the group consisting of H, an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
- R2 and R3 are independently selected from the group consisting of an alkyl group, alkenyl group, alkynyl group, alkoxy group, aryl group, heteroaryl group, cyano group, nitro group, phosphate group and sulfoxyl group;
- X represents —(CHxYy)z—, wherein x+y=2, x=0, 1 or 2, y=0, 1 or 2 and z=2 to 4;
- Y1 and Y2 are independently selected from S, SO2, N, N-alkyl, or 0.
Dependencies are inferred from the claim text.