Dyes and labeled molecules

• US 9,580,749 B2
• Filed: 08/15/2013
• Issued: 02/28/2017
• Est. Priority Date: 03/17/2005
• Status: Active Grant

• Current Assignee: Allelogic Biosciences Corporation, Biotium, Inc.
• Original Assignee: Biotium, Inc.
• Inventors: Mao, Fei, Leung, Wai-Yee, Xin, Xing
• Primary Examiner(s): Riley, Jezia
• Application Number:
  US13/968,122
• Publication Number:
  US 20140106349A1
• Time in Patent Office: 1,293 Days
• Field of Search: 536/26.6, 435/6.1, 435/91.1
• US Class Current: 1/1
• CPC Class Codes: C07D 209/08 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 213/38 having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
• CPC Class Codes: C07D 221/10 Aza-phenanthrenes
• CPC Class Codes: C07D 417/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C07D 491/147 the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
• 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 15/00 Acridine dyes
• CPC Class Codes: C12Q 1/6851 Quantitative amplification
• CPC Class Codes: C12Q 1/686 Polymerase chain reaction [PCR]
• CPC Class Codes: C12Q 1/6876 Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes
• CPC Class Codes: C12Q 2563/173 staining/intercalating agent, e.g. ethidium bromide

Abstract

Dimeric and trimeric nucleic acid dyes, and associated systems and methods are provided. Such a dye may form a hairpin-like structure that enables it to stain nucleic acids via a release-on-demand mechanism, for example. Such a dye may have low background fluorescence in the absence of nucleic acids and high fluorescence in the presence of nucleic acids, upon binding therewith, for example. A dye provided herein may be useful in a variety of applications, such as in DNA quantitation in real-time PCR, for example.

Claims

1. A labeled biomolecule having a structure of

2. The labeled biomolecule according to claim 1, wherein the BRIDGE is a substantially aliphatic linker comprising from about 15 to about 150 non-hydrogen atoms and up to one positive charge.

3. The labeled biomolecule according to claim 1, wherein B is selected from a nucleotide, an oligonucleotide, a peptide, a protein, a hapten, a drug, a microparticle, a synthetic polymer, a natural polymer, a biological cell, and a virus.

4. The labeled biomolecule according to claim 3, wherein B is a nucleotide or an oligonucleotide.

5. The labeled biomolecule according to claim 1, wherein Q₁ and Q₂ are each independently an asymmetric cyanine dye.

6. The labeled biomolecule according to claim 5, wherein Q₁ and Q₂ are each thiazole orange.