US5714331A
Expired / Lapsed
US
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Peptide nucleic acids having enhanced binding affinity, sequence specificity and solubility
Assignee: ExxonMobil Chemical Patents Inc
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Filing: 1996-07-24
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Granted: 1998-02-03
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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 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 06:58
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: 11
Claim 1
Independent Claim
97 words
A method for enhancing the solubility of a peptide nucleic acid by incorporating C 1 -C 8 alkylamine side chain in said peptide nucleic acid having the 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
97 words
A method for enhancing the solubility of a peptide nucleic acid by incorporating C 1 -C 8 alkylamine side chain in said peptide nucleic acid having the 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.
References Cited (Backward Citations)
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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) | 2001-02-02 | 2001-08-04 | 2002-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-02-02 | 2005-08-04 | 2006-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-02-02 | 2009-08-04 | 2010-02-03 | $7700.00 | Window Closed / Lapsed |