US5736336A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility
Assignee: Individual
•
Filing: 1997-05-01
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Granted: 1998-04-07
•
Expires: 2017-05-01
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 solubility. The peptide nucleic acids comprise ligands selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases attached to a polyamide backbone, and contain C 1 -C 8 alkylamine side chains. Methods of enhancing the solubility, binding affinity and sequence specificity of PNAs are provided.
Inventors
- 👤 Ole Buchardt, deceased
- 👤 representative by Dorte Buchardt
- 👤 Michael Egholm
- 👤 Peter Eigil Nielsen
- 👤 Rolf Henrik Berg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:35
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: 22
Claim 1
Independent Claim
100 words
A method for enhancing the DNA or RNA sequence specificity of a peptide nucleic acid by incorporating C 1 -C 8 akylamine side chain 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; each R 7' is independently hydrogen or C 1 -C 8 alkylamine, provided that at least one R 7' is 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
100 words
A method for enhancing the DNA or RNA sequence specificity of a peptide nucleic acid by incorporating C 1 -C 8 akylamine side chain 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; each R 7' is independently hydrogen or C 1 -C 8 alkylamine, provided that at least one R 7' is 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
19 words
The method of claim 1 wherein at least one of said R 7' is C 3 -C 6 alkylamine.
Claim 4
Dependent Claim
17 words
The method of claim 2 wherein at least one R 7' is C 4 -C 5 alkylamine.
Claim 5
Dependent Claim
13 words
The method of claim 3 wherein at least one R 7' is butylamine.
Claim 6
Dependent Claim
14 words
The method of claim 4 wherein substantially all of the R 7' are butylamine.
Claim 7
Dependent Claim
24 words
The method of claim 1 wherein at least one of the carbon atom to which the substituent R 7' is attached is stereochemically enriched.
Claim 8
Dependent Claim
14 words
The method of claim 6 wherein said stereochemical enrichment is of the R configuration.
Claim 9
Dependent Claim
14 words
The method of claim 7 wherein substantially all of the R 7' are butylamine.
Claim 10
Dependent Claim
16 words
The method of claim 1 wherein said peptide nucleic acid is derived from an amino acid.
Claim 11
Dependent Claim
14 words
The method of claim 9 wherein said peptide nucleic acid is derived from D-lysine.
Claim 12
Independent Claim
101 words
A method for enhancing the DNA or RNA binding affinity of a peptide nucleic acid by incorporating C 1 -C 8 alkylamine side chain in said peptide nucleic acid having the formula: ##STR4## wherein: each L is independently selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases; each R 7' is independently hydrogen or C 1 -C 8 alkylamine, provided that at least one R 7' is 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 13
Independent Claim
101 words
A method for enhancing the DNA or RNA binding affinity of a peptide nucleic acid by incorporating C 1 -C 8 alkylamine side chain in said peptide nucleic acid having the formula: ##STR4## wherein: each L is independently selected from a group consisting of naturally-occurring nucleobases and non-naturally-occurring nucleobases; each R 7' is independently hydrogen or C 1 -C 8 alkylamine, provided that at least one R 7' is 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 14
Dependent Claim
19 words
The method of claim 11 wherein at least one of said R 7' is C 3 -C 6 alkylamine.
Claim 15
Dependent Claim
17 words
The method of claim 12 wherein at least one R 7' is C 4 -C 5 alkylamine.
Claim 16
Dependent Claim
13 words
The method of claim 13 wherein at least one R 7' is butylamine.
Claim 17
Dependent Claim
14 words
The method of claim 14 wherein substantially all of the R 7' are butylamine.
Claim 18
Dependent Claim
24 words
The method of claim 11 wherein at least one of the carbon atom to which the substituent R 7' is attached is stereochemically enriched.
Claim 19
Dependent Claim
14 words
The method of claim 16 wherein said stereochemical enrichment is of the R configuration.
Claim 20
Dependent Claim
14 words
The method of claim 17 wherein substantially all of the R 7' are butylamine.
Claim 21
Dependent Claim
16 words
The method of claim 11 wherein said peptide nucleic acid is derived from an amino acid.
Claim 22
Dependent Claim
14 words
The method of claim 19 wherein said peptide nucleic acid is derived from D-lysine.
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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) | 2001-04-06 | 2001-10-06 | 2002-04-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-04-06 | 2005-10-06 | 2006-04-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-04-06 | 2009-10-06 | 2010-04-07 | $7700.00 | Window Closed / Lapsed |