US 5,705,333 AGranted

Peptide-based nucleic acid mimics(PENAMS)

AssigneeThe Regents of the University of California

InventorsVibhakar J. Shah, George L. Kenyon, Irwin D. Kuntz

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Abstract

The present invention provides novel nucleic acid mimics (termed "PENAMs") comprising a peptidic backbone and nucleotidic sidechains; the sidechains being oriented in such a way that the PENAM is homomorphous to target nucleic acids with which it can effectively hydrogen bond. Homomorphism is achieved by the incorporation of unusual sterochemical centers, including D-chiral centers and quasi-chiral centers, into the peptidic backbone. The PENAMs are useful for targeting nucleic acid sequences in order to modulate their activity in an "antisense" manner. Targeting can also be used to detect, isolate or modify target nucleic acids.

Claims24

Dependent claims

A composition useful in targeting a nucleic acid comprising a stereochemically-selected population of peptide-based nucleic acid mimics (PENAMs) each member of which comprises a sequence of at least about 4 NuAA monomers,

wherein said NuAA monomers are each of the following formula:
##STR7## wherein:
E is carbon (C) or nitrogen (N);
W is hydrogen or a spacer group;
Y is hydrogen or a spacer group (when E is carbon), or Y is a lone pair of electrons (when E is nitrogen);
S 1 is a bond or a first spacer group;
S2 is a bond or a second spacer group;
S3 is a bond or a third spacer group;
X is oxygen (O) or sulfur (S);
B is a base segment comprising a nucleotidic base or an analog thereof;
and
N is nitrogen,
and wherein at least one of said PENAMs is a homomorphicaily-preferred PENAM comprising a D-chiral center and wherein said homomorphically-preferred PENAM makes up at least about 10% of the stereochemically-selected population of PENAMs wherein said D-chiral center is located within a NuAA at position E wherein E is carbon.

10 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/286,875Filed 5 Aug 1994
Granted: 6 Jan 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

C12Q 1/6811
Involving nucleic acids: selection methods for production or design of target specific oligonucleotides or binding molecules
C07K 14/003
By chemical synthesis: peptide-nucleic acids
C12Q 1/6813
Involving nucleic acids: hybridisation assays
Y10T 436/143333
Hetero-O [e.g., ascorbic acid, etc.]: saccharide [e.g., DNA, etc.]

Family

No related US applications are recorded in the indexed filing history.

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