US5766855A
Expired / Lapsed
US
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Peptide nucleic acids having enhanced binding affinity and sequence specificity
Assignee: Individual
•
Filing: 1996-07-24
•
Granted: 1998-06-16
•
Expires: 2016-07-24
Abstract
Abstract A novel class of compounds, known as peptide nucleic acids, bind complementary DNA and RNA strands more strongly than a corresponding DNA strand, and exhibit increased sequence specificity and binding affinity. Methods of increasing binding affinity and sequence specificity of peptide nucleic acids are provided wherein some peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, while other peptide nucleic acids contain at least one 2,6-diaminopurine nucleobase and at least one C1-C8 alkylamine side chain.
Inventors
- 👤 Ole Buchardt, deceased
- 👤 Michael Egholm
- 👤 Peter Eigil Nielsen
- 👤 Rolf Henrik Berg
- 👤 executor by Dorte Buchardt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:02
CPC Classifications
C; C07; C07H; C07H21/00; C07K; C07K14/00; C07K14/001; C07K14/003; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/06026; C07K5/06139; C07K7/00; C07K7/04; C07K7/06; C07K7/08; C12; C12Q; C12Q1/00; C12Q1/68; C12Q1/6813; C12Q1/6869; A; A61; A61K; A61K38/00; Y; Y10; Y10S; Y10S435/00; Y10S435/81
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
92 words
A method for enhancing the DNA or RNA sequence specificity of a peptide nucleic acid by incorporating a 2,6-diaminopurine nucleobase in said peptide nucleic acid having formula: ##STR3## wherein: each L is independently selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, provided that at least one L is 2,6-diaminopurine nucleobase; each R 7' is independently hydrogen or C 1 -C 8 alkylamine; R h is OH, NH 2 or NHLysNH 2 ; R i is H, COCH 3 or t-butoxycarbonyl; and n is an integer from 1 to 30.
Claim 2
Independent Claim
92 words
A method for enhancing the DNA or RNA sequence specificity of a peptide nucleic acid by incorporating a 2,6-diaminopurine nucleobase in said peptide nucleic acid having formula: ##STR3## wherein: each L is independently selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, provided that at least one L is 2,6-diaminopurine nucleobase; each R 7' is independently hydrogen or C 1 -C 8 alkylamine; R h is OH, NH 2 or NHLysNH 2 ; R i is H, COCH 3 or t-butoxycarbonyl; and n is an integer from 1 to 30.
Claim 3
Dependent Claim
16 words
The method of claim 1 wherein said each R 7' is C 3 -C 6 alkylamine.
Claim 4
Dependent Claim
16 words
The method of claim 2 wherein said each R 7' is C 4 -C 5 alkylamine.
Claim 5
Dependent Claim
12 words
The method of claim 3 wherein said each R 7' is butylamine.
Claim 6
Dependent Claim
19 words
The method of claim 1 wherein at least one of said R 7' is C 3 -C 6 alkylamine.
Claim 7
Dependent Claim
19 words
The method of claim 5 wherein at least one of said R 7' is C 4 -C 5 alkylamine.
Claim 8
Dependent Claim
15 words
The method of claim 6 wherein at least one of said R 7' is butylamine.
Claim 9
Dependent Claim
14 words
The method of claim 7 wherein substantially all of said R 7' is butylamine.
Claim 10
Dependent Claim
20 words
The method of claim 1 wherein the carbon atom to which the substituent R 7' is attached is stereochemically enriched.
Claim 11
Dependent Claim
14 words
The method of claim 9 wherein said stereochemical enrichment is of the R configuration.
Claim 12
Dependent Claim
16 words
The method of claim 1 wherein said peptide nucleic acid is derived from an amino acid.
Claim 13
Dependent Claim
14 words
The method of claim 11 wherein said peptide nucleic acid is derived from D-lysine.
Claim 14
Independent Claim
92 words
A method for enhancing the DNA or RNA binding affinity of a peptide nucleic acid by incorporating a 2,6-diaminopurine nucleobase in said peptide nucleic acid having formula: ##STR4## wherein: each L is independently selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, provided that at least one L is 2,6-diaminopurine nucleobase; each R 7' is independently hydrogen or C 1 -C 8 alkylamine; R h is OH, NH 2 or NHLysNH 2 ; R i is H, COCH 3 or t-butoxycarbonyl; and n is an integer from 1 to 30.
Claim 15
Independent Claim
92 words
A method for enhancing the DNA or RNA binding affinity of a peptide nucleic acid by incorporating a 2,6-diaminopurine nucleobase in said peptide nucleic acid having formula: ##STR4## wherein: each L is independently selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases, provided that at least one L is 2,6-diaminopurine nucleobase; each R 7' is independently hydrogen or C 1 -C 8 alkylamine; R h is OH, NH 2 or NHLysNH 2 ; R i is H, COCH 3 or t-butoxycarbonyl; and n is an integer from 1 to 30.
Claim 16
Dependent Claim
16 words
The method of claim 13 wherein said each R 7' is C 3 -C 6 alkylamine.
Claim 17
Dependent Claim
16 words
The method of claim 14 wherein said each R 7' is C 4 -C 5 alkylamine.
Claim 18
Dependent Claim
12 words
The method of claim 15 wherein said each R 7' is butylamine.
Claim 19
Dependent Claim
19 words
The method of claim 13 wherein at least one of said R 7' is C 3 -C 6 alkylamine.
Claim 20
Dependent Claim
19 words
The method of claim 17 wherein at least one of said R 7' is C 4 -C 5 alkylamine.
Claim 21
Dependent Claim
15 words
The method of claim 18 wherein at least one of said R 7' is butylamine.
Claim 22
Dependent Claim
14 words
The method of claim 19 wherein substantially all of said R 7' is butylamine.
Claim 23
Dependent Claim
20 words
The method of claim 13 wherein the carbon atom to which the substituent R 7' is attached is stereochemically enriched.
Claim 24
Dependent Claim
14 words
The method of claim 21 wherein said stereochemical enrichment is of the R configuration.
Claim 25
Dependent Claim
16 words
The method of claim 13 wherein said peptide nucleic acid is derived from an amino acid.
Claim 26
Dependent Claim
14 words
The method of claim 23 wherein said peptide nucleic acid is derived from D-lysine.
References Cited (Backward Citations)
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WO1990002749A1
Cited
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WO1992020702A1
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US5340716A
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WO1994006815A1
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-06-15 | 2001-12-15 | 2002-06-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-06-15 | 2005-12-15 | 2006-06-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-06-15 | 2009-12-15 | 2010-06-16 | $7700.00 | Window Closed / Lapsed |