Dark quenchers for donor-acceptor energy transfer

• US 20060035262A1
• Filed: 09/13/2005
• Published: 02/16/2006
• Est. Priority Date: 05/09/2000
• Status: Abandoned Application

• Current Assignee: HSB Corporate Trust Company (UK) Limited
• Original Assignee: Biosearch Technologies Incorporated
• Inventors: Lyttle, Matt, Cook, Ronald M., Dick, Daren
• Application Number:
  US11/226,852
• Publication Number:
  US 20060035262A1
• Time in Patent Office: Days
• US Class Current: 435/6
• CPC Class Codes: C07B 2200/11 Compounds covalently bound to a solid support
• CPC Class Codes: C07C 245/08 with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
• CPC Class Codes: C07D 241/46 Phenazines
• CPC Class Codes: C07F 9/091 with hydroxyalkyl compounds with further substituents on alkyl
• CPC Class Codes: C07F 9/2408 of hydroxyalkyl compounds
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C09B 31/043 Amino-benzenes
• CPC Class Codes: C09B 56/00 Azo dyes containing other chromophoric systems
• CPC Class Codes: C09B 56/12 Anthraquinone-azo dyes from diazotised aminoanthracene C09B29/0022, azo dyes containing hydroxyl groups acylated with polyfunctional anthraquinone derivatives C09B43/26
• CPC Class Codes: C12Q 1/6818 involving interaction of two or more labels, e.g. resonant energy transfer
• CPC Class Codes: C40B 40/00 Libraries per se, e.g. arrays, mixtures
• CPC Class Codes: G01N 33/542 with steric inhibition or signal modification, e.g. fluorescent quenching
• CPC Class Codes: G01N 33/582 with fluorescent label

Abstract

The present invention provides a family of dark quenchers, termed Black Hole Quenchers (“BHQs”), that are efficient quenchers of excited state energy but which are themselves substantially non-fluorescent. Also provided are methods of using the BHQs, probes incorporating the BHQs and methods of using the probes.

Claims

1-87. -87. (canceled)

88. A compound having the formula:

99. A compound of claim 88 wherein W is acylic.

100. A compound of claim 88 wherein W comprises a cyclic group.

89. A compound having the formula:

101. A compound of claim 89 wherein W is a cyclic.

102. A compound of claim 89 wherein W comprises a cyclic group.

90. A compound having the formula:

103. A compound of claim 90 wherein W is acyclic.

104. A compound of claim 90 wherein W comprises a cyclic group.

91. A compound having the formula:

92. A compound of claim 91 wherein Ar¹ is directly substituted with Ar³.

93. A compound of claim 91 wherein Ar¹ is indirectly substituted with Ar³.

94. A compound of claim 91 wherein A² is directly substituted with Ar³.

95. A compound of claim 91 wherein Ar² is indirectly substituted with Ar³.

105. A compound of claim 91 wherein W is acyclic.

106. A compound of claim 91 wherein W comprises a cyclic group.

107. A compound of claim 92 wherein W is acyclic.

108. A compound of claim 92 wherein W comprises a cyclic group.

109. A compound of claim 93 wherein W is a cyclic.

110. A compound of claim 93 wherein W comprises a cyclic group.

111. A compound of claim 94 wherein W is acyclic.

112. A compound of claim 94 wherein W comprises a cyclic group.

113. A compound of claim 95 wherein W is acyclic.

114. A compound of claim 95 wherein W comprises a cyclic group.

121. A compound of claims 89, 91-95 or 105-114 wherein X₂ is a phosphoramidite.

96. A compound having the formula:

115. A compound of claim 96 wherein W is acyclic.

116. A compound of claim 96 wherein W comprises a cyclic group.

97. A compound having the formula:

117. A compound of claim 97 wherein W is cyclic.

118. A compound of claim 97 wherein W comprises a cyclic group.

98. A compound having the formula:

119. A compound of claim 98 wherein W is acyclic.

120. A compound of claim 98 wherein W comprises a cyclic group.