US 2003/0199431 A1Published application

Modified peptide nucleic acid (PNA) molecules

OwnerPeter E. Nielsen, Liam Good +6inventors

InventorsPeter E. Nielsen, Liam Good, Henrik Frydenlund Hansen, Frederik Beck, Leila Malik, Carsten Schou, Margit Wissenbach, Birgit Kjaeldgaard Giwercman

Life of this patent

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Abstract

The present invention relates to novel drugs which may be used in combating infectious micro-organisms, particularly bacteria. More specifically, the invention relates to peptide nucleic acid (PNA) sequences that are modified by conjugating cationic peptides to the PNA moiety in order to obtain novel PNA molecules that exhibit enhanced anti-infective properties

Claims47

Dependent claims

A modified oligonucleotide having formula (III):

Peptide-L-Oligon (III)
wherein L is a linker or a bond, Peptide is any amino acid sequence, and Oligon is an oligonucleotide or analog thereof.

A modified PNA molecule comprising:

29 H-KFFKFFKFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
24) H-FFKFFKFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
25) H-FKFFKFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
26) H-KFFKFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
27) H-FFKFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
28) H-FKFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
29) H-KFFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
30) H-FFK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
31) H-FK-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
32) H-K-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
33) H-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
34) H-KFFKFFKFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
35) H-FFKFFKFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
36) H-FKFFKFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
37) H-KFFKFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
38) H-FFKFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
39) H-FKFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
40) H-KFF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
41) H-FF-ado-CATAGCTGTTTC-NH2, (SEQ ID NO:
42) H-F-ado-CATAGCTGTTC-NH2, (SEQ ID NO:
43) H-KFFKFFKFFK-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
18) H-KFFKFFKFFK-ado-TGA CTA GAT GAG-NH2, (SEQ ID NO:
44) H-KFFKFFKFFK-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
45) H-FFKFFKFFK-GGC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
53) H-FFRFFRFFR-GGC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
54) H-LLKLLKLLK-GGC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
55) H-LLRLLRLLR-GGC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
56) H-LLKKLAKALK-GC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
57) H-KRRWPWWPWKK-C-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
58) H-KFKVKFVVKK-GC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
59) H-LLKLLLKLLLK-C-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
60) H-FFKFFKFFK-GGC-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
61) H-KFFKFFKFFK-C-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
62) H-F-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
63) H-FF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
64) H-KFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
65) H-FKFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
66) H-FFKFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
67) H-KFFKFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
68) H-FKFFKFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
69) H-FFKFFKFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
70) H-KFFKFFKFF-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
71) H-LLKKLAKALKG-ahex-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
21) H-LLKKLAKALKG-ado-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
72) H-KFFKFFKFFK-ado-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
73) H-KFFKFFKFFK-ahex-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
74) H2N-KFFKFFKFFK-C-smcc-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
75) H2N-LLKKLAKALK-GC-smcc-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
76) H2N-KFFKFF-C-smcc-ado-CCA TCT AAT CCT-NH2, (SEQ ID NO:
77) H-ado-TTC AAA CAT AGT-Nh2, (SEQ ID NO:
78) H2N-KFFKVKFVVKK-C-smcc-ado-TTC AAA CAT AGT-NH2, (SEQ ID NO:
79) H2N-KFFKVKFVVKK-C-smcc-ado-TTG TGC CCC GTC-NH2, (SEQ ID NO:
80) H2N-KKFKVKFVVKKC-achc-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
81) H-KFFKFFKFFK-achc-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
82) H2N-KKFKVKFVVKKC-lcsmcc-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
83) H2N-KKFKVKFVVKKC-mbs-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
84) H2N-KKFKVKFVVKKC-emcs-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
85) H2N-KKFKVKFVVKKC-smph-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
86) H2N-KKFKVKFVVKKC-amas-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
87) H2N-KKFKVKFVVKKC-smpb-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
88) H2N-KKFKVKFVVKKC-lcsmcc-gly-TTCAAACATAGT-NH2, (SEQ ID NO:
89) H2N-KKFKVKFVVKKC-lcsmcc-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
90) H2N-KKFKVKFVVKKC-lcsmcc-β.cypr-TTCAAACATAGT-NH2, (SEQ ID NO:
91) H2N-KKFKVKFVVKKC-lcsmcc-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
92) H2N-KKFKVKFVVKKC-lcsmcc-adc-TTCAAACATAGT-NH2, (SEQ ID NO:
93) H-KFFKFFKFFK-ado-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
94) H-KFFKFFKFFK-ado-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
95) H-KFFKFFKFFK-ado-P-TTCAAACATAGT-NH2, (SEQ ID NO:
96) H-KFFKFFKFFK-ado-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
97) H-KFFKFFKFFK-ado-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
98) H-KFFKFFKFFK-ado-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
99) H-KFFKFFKFFK-Gly-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
100) H-KFFKFFKFFK-Gly-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
101) H-KFFKFFKFFK-Gly-P-TTCAAACATAGT-NH2, (SEQ ID NO:
102) H-KFFKFFKFFK-Gly-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
103) H-KFFKFFKFFK-Gly-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
104) H-KFFKFFKFFK-Gly-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
105) H-KFFKFFKFFK-P-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
106) H-KFFKFFKFFK-P-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
107) H-KFFKFFKFFK-P-P-TTCAAACATAGT-NH2, (SEQ ID NO:
108) H-KFFKFFKFFK-P-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
109) H-KFFKFFKFFK-P-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
110) H-KFFKFFKFFK-P-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
111) H-KFFKFFKFFK-aha-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
112) H-KFFKFFKFFK-aha-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
113) H-KFFKFFKFFK-aha-P-TTCAAACATAGT-NH2, (SEQ ID NO:
114) H-KFFKFFKFFK-aha-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
115) H-KFFKFFKFFK-aha-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
116) H-KFFKFFKFFK-aha-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
117) H-KFFKFFKFFK-β.ala-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
118) H-KFFKFFKFFK-β.ala-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
119) H-KFFKFFKFFK-β.ala-P-TTCAAACATAGT-NH2, (SEQ ID NO:
120) H-KFFKFFKFFK-β.ala-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
121) H-KFFKFFKFFK-β.ala-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
122) H-KFFKFFKFFK-β.ala-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
123) H-KFFKFFKFFK-P-p-TTCAAACATAGT-NH2, (SEQ ID NO:
124) H-KFFKFFKFFK-P-P-TTCAAACATAGT-NH2, (SEQ ID NO:
125) H-KFFKFFKFFK-K-K-TTCAAACATAGT-NH2, (SEQ ID NO:
126) H-KFFKFFKFFK-F-F-TTCAAACATAGT-NH2, (SEQ ID NO:
127) H-KFFKFFKFFK-F-K-TTCAAACATAGT-NH2, (SEQ ID NO:
128) H-KFFKFFKFFK-K-F-TTCAAACATAGT-NH2, (SEQ ID NO:
129) H-KFFKFFKFFK-phg-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
130) H-KFFKFFKFFK-phg-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
131) H-KFFKFFKFFK-phg-P-TTCAAACATAGT-NH2, (SEQ ID NO:
132) H-KFFKFFKFFK-phg-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
133) H-KFFKFFKFFK-phg-β.ala-TTCAAACATAGT-NH2, (SEQ ID NO:
134) H-KFFKFFKFFK-phg-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
135) H-KFFKFFKFFK-achc-ado-TTCAAACATAGT-NH2, (SEQ ID NO:
136) H-KFFKFFKFFK-achc-Gly-TTCAAACATAGT-NH2, (SEQ ID NO:
137) H-KFFKFFKFFK-achc-P-TTCAAACATAGT-NH2, (SEQ ID NO:
138) H-KFFKFFKFFK-achc-aha-TTCAAACATAGT-NH2, (SEQ ID NO:
139) H-KFFKFFKFFK-achc-β.ala-TTCAAACATAGT-NH2 or (SEQ ID NO:
140) H-KFFKFFKFFK-achc-achc-TTCAAACATAGT-NH2, (SEQ ID NO:
141).

111 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/109,274Filed 27 Mar 2002
Priority: DK PA 1999 0146713 Oct 1999
Published: 23 Oct 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C12N 15/113
DNA or RNA fragments; Modified forms thereof ; Non-coding nucleic acids having a biological activity: non-coding nucleic acids modulating the…
A61K 47/62
The non-active ingredient being a modifying agent: the modifying agent being a protein, peptide or polyamino acid
A61L 2/16
Disinfection or sterilisation of materials or objects, in general; Accessories therefor: using chemical substances
A61K 38/00
Medicinal preparations containing peptides

Family

Application60/159,684Us provisional application · filed 15 Oct 1999
Application60/159,679Us provisional application · filed 15 Oct 1999
Application60/211,758Us provisional application · filed 14 Jun 2000
Application60/211,878Us provisional application · filed 14 Jun 2000
Application60/211,435Us provisional application · filed 14 Jun 2000
Application09/689,155Division · filed 12 Oct 2000
Application10/109,274Division · filed 27 Mar 2002
US 6,548,651 B1Related patent
US 2003/0199431 A1This patent

From the US filing history. Foreign family members aren’t listed.

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