METHOD FOR SELECTIVE LOCALIZATION OF ACTIVE AGENTS AT AND IN MITOCHONDRIA AND CORRESPONDING ACTIVE AGENTS
First Claim
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1. Compound of the formula I, wherein n represents an integer from 0 to 35, each E independently of each other represents a hydrogen atom, a substituted or unsubstituted phenyl rest, a substituted or unsubstituted heterocycle, a nucleobase, optionally substituted with protecting groups, or a DNA intercalator, each R1 independently of each other represents a hydrogen atom or a side chain of a naturally occurring or non-naturally occurring amino acid, or an optionally substituted alkyl, alkenyl, alkylaryl, aryl, heterocyclic or alicyclic rest having up to 20 carbon atoms, wherein at least one of the optionally substituted alkyl, alkenyl, alkylaryl, aryl, heterocyclic or alicyclic rests having up to 20 carbon atoms is substituted with one or more phosphonic acid ester functions or phosphononic acid functions, K represents a group of the formula —
- NR2R3, —
N⊕
R2R3R4, —
NR2(CO)R3 or —
NR2(CS)R3, wherein R2, R3 and R4 independently of each other represent a hydrogen atom, an alkyl, alkaryl, alkenyl, or alkinyl rest, amino protecting group, reporter ligand, fluorescence marker, intercalator, chelator, amino acid, peptide, protein, carbohydrate, lipid, steroid, fatty acid, oligonucleotide, quantum dot, FRET quencher (fluorescence resonance energy transfer quencher) or a polymer soluble or insoluble in water, wherein each of the above mentioned rests optionally may be substituted, L represents a group of the formula —
NR5R6, —
NR5(CO)R6, —
NR5(CS)R6, —
OR7 or —
SR7, wherein R5 and R6 independently of each other represent a hydrogen atom, an alkyl, alkaryl, alkenyl, or alkinyl rest, reporter ligand, fluorescence marker, intercalator, chelator, amino acid, amino acid amide, peptide, peptide amide, protein, carbohydrate, lipid, steroid, fatty acid, oligonucleotide, quantum dot, FRET quencher (fluorescence resonance energy transfer quencher) or a polymer soluble or insoluble in water, and wherein R7 represents a hydrogen atom, an alkyl rest, reporter ligand, fluorescence marker, intercalator, chelator, amino acid, amino acid amide, peptide, peptide amide, protein, carbohydrate, lipid, steroid, fatty acid, oligonucleotide, quantum dot, FRET quencher or a polymer soluble or insoluble in water, wherein each of the above mentioned rests optionally may be substituted, wherein the rests K, L or R1 independently of each other are substituted with at least one monohydroxy mononitrophenyl rest or monohydroxy dinitrophenyl rest.
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Abstract
The present invention relates to novel methods for selective localization of active agents both at and in mitochondria within living cells, as well as corresponding active agents that penetrate through the cell membrane into the cells without further adjuvants and there can be localized both at and in mitochondria. These active agents are substituted with at least one monohydroxy mononitrophenyl rest or monohydroxy dinitrophenyl rest.
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Citations
55 Claims
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1. Compound of the formula I,
wherein n represents an integer from 0 to 35, each E independently of each other represents a hydrogen atom, a substituted or unsubstituted phenyl rest, a substituted or unsubstituted heterocycle, a nucleobase, optionally substituted with protecting groups, or a DNA intercalator, each R1 independently of each other represents a hydrogen atom or a side chain of a naturally occurring or non-naturally occurring amino acid, or an optionally substituted alkyl, alkenyl, alkylaryl, aryl, heterocyclic or alicyclic rest having up to 20 carbon atoms, wherein at least one of the optionally substituted alkyl, alkenyl, alkylaryl, aryl, heterocyclic or alicyclic rests having up to 20 carbon atoms is substituted with one or more phosphonic acid ester functions or phosphononic acid functions, K represents a group of the formula — - NR2R3, —
N⊕
R2R3R4, —
NR2(CO)R3 or —
NR2(CS)R3, wherein R2, R3 and R4 independently of each other represent a hydrogen atom, an alkyl, alkaryl, alkenyl, or alkinyl rest, amino protecting group, reporter ligand, fluorescence marker, intercalator, chelator, amino acid, peptide, protein, carbohydrate, lipid, steroid, fatty acid, oligonucleotide, quantum dot, FRET quencher (fluorescence resonance energy transfer quencher) or a polymer soluble or insoluble in water, wherein each of the above mentioned rests optionally may be substituted,L represents a group of the formula —
NR5R6, —
NR5(CO)R6, —
NR5(CS)R6, —
OR7 or —
SR7, wherein R5 and R6 independently of each other represent a hydrogen atom, an alkyl, alkaryl, alkenyl, or alkinyl rest, reporter ligand, fluorescence marker, intercalator, chelator, amino acid, amino acid amide, peptide, peptide amide, protein, carbohydrate, lipid, steroid, fatty acid, oligonucleotide, quantum dot, FRET quencher (fluorescence resonance energy transfer quencher) or a polymer soluble or insoluble in water, and wherein R7 represents a hydrogen atom, an alkyl rest, reporter ligand, fluorescence marker, intercalator, chelator, amino acid, amino acid amide, peptide, peptide amide, protein, carbohydrate, lipid, steroid, fatty acid, oligonucleotide, quantum dot, FRET quencher or a polymer soluble or insoluble in water, wherein each of the above mentioned rests optionally may be substituted,wherein the rests K, L or R1 independently of each other are substituted with at least one monohydroxy mononitrophenyl rest or monohydroxy dinitrophenyl rest. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 45, 46, 47, 48)
- NR2R3, —
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29. Compound of the formula V,
Z-M-P-
Vwherein Z represents a functional group capable of oxidation or reduction, M represents a linker group, and P represents a monohydroxy mononitrophenyl rest or a monohydroxy dinitrophenyl rest. - View Dependent Claims (34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 49, 50, 51, 52, 53, 54, 55)
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- 30. Method for selective localization of a compound both at and in mitochondria, wherein the compound is substituted with at least one monohydroxy mononitrophenyl rest or monohydroxy dinitrophenyl rest.
Specification
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Current Assigneeugichem Gesellschaft fur organische Chemie mbH
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Original Assigneeugichem Gesellschaft fur organische Chemie mbH
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InventorsWerner, Birgit, Lindhorst, Thomas, Piper, Stefan
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current514/1.100
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