Azo compound, use thereof and method for preparing same
Inventors
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Assignees
Member
BioneerBioneer is a biotechnology company specializing in molecular biology, offering solutions in nucleic acid synthesis, molecular diagnostics, protein production, and laboratory automation. The company's expertise covers oligonucleotide chemistry, gene synthesis, sample preparation, molecular diagnostics, and analytical services such as mass spectrometry and sequencing, serving clinical, research, and industrial sectors globally.
Bioneer is a biotechnology company specializing in molecular biology, offering solutions in nucleic acid synthesis, molecular diagnostics, protein production, and laboratory automation. The company's expertise covers oligonucleotide chemistry, gene synthesis, sample preparation, molecular diagnostics, and analytical services such as mass spectrometry and sequencing, serving clinical, research, and industrial sectors globally.
Publication Number
US-10167391-B2
Publication Date
2019-01-01
Expiration Date
Abstract
The present invention provides a novel azo compound having a quenching ability for the material that exhibits a luminescent phenomenon at an excited energy level, a quencher comprising the novel azo compound, a use of the quencher and a method for preparing the azo compound. The quencher according to the present invention may exhibit excellent characteristics in a wavelength absorption region.
Core Innovation
The invention relates to a quencher comprising a compound represented by formula 1 in which A1, A2, and A3 have defined structures of formula 2 or formula 3, formula 4, and formula 5, respectively. The variables Z1 to Z4, X1 to X2, Z10 to Z13, Z14 to Z17, Z18, and linker-like groups L1 and L2 are constrained to specific allowed groups, including a proviso that all CR3 are not simultaneously hydrogen.
In defined embodiments, the quencher is further refined by selecting particular formula-defined variants for Z18, L1, L2, and R15 to R18, including a proviso that in formula 7 all R15 to R18 are not simultaneously hydrogen. The disclosed scope is directed to azo compound structures represented by formulas 6 and 7, with the same variable-group constraints.
The document also describes a sequential azo coupling approach in which azo coupling reactions build the azo compounds of formulas 6 and 7 through intermediate formulae. The resulting quenchers include examples in which quencher 570 is bound to oligonucleotides and evaluated by emission intensity measurements and RT-PCR, demonstrating quenching performance comparable to conventional BHQ controls.
Claims Coverage
The independent claim coverage includes two formula-based families: a quencher defined by a multi-part scaffold with constrained substituent identities and a hydrogen proviso, and an azo compound defined by formulas 6 and 7 with constrained substituent identities and a non-all-hydrogen proviso.
Quencher defined by formula 1 with constrained substituents and hydrogen proviso
A quencher comprising a compound represented by formula 1 where A1, A2, and A3 have structures of formulas 2 or 3, 4, and 5, respectively, with Z1–Z4, X1–X2, Z10–Z13, Z14–Z17, Z18, and L1/L2 each limited to stated options, including the proviso that all CR3 are not simultaneously hydrogen.
Azo compound selected from formulas 6 and 7 with substituent constraints and non-all-hydrogen proviso
An azo compound selected from compounds represented by formulas 6 and 7 where Z18 is CH or nitrogen; L1 and L2 are each independently hydrogen or selected C1–C30 groups including hydroxy-substituted, carboxyl, or carbonyloxy-substituted alkyl groups; and R15 to R18 are each independently H, C1–C10 alkoxy, or C1–C10 alkyl, with the proviso that in formula 7 all R15 to R18 are not simultaneously hydrogen.
Overall, the claims cover specific quencher compounds defined by a constrained formula-1 scaffold with defined A1/A2/A3 substructures, variable-group limits, and a non-all-hydrogen constraint, and specific azo compounds defined by formulas 6 and 7 with corresponding constrained substituent identities and an additional proviso that in formula 7 the R15–R18 substituents are not all hydrogen.
Stated Advantages
Broad/strong absorption wavelength region enabling use with multiple fluorophores.
Improved stability during oligomer synthesis/purification.
Demonstrated quenching performance comparable to conventional BHQ controls.
Documented Applications
Real-time PCR and nucleic-acid detection compositions using reporter fluorophores in contexts described with the disclosed quencher and probes/oligonucleotides.
Nucleic-acid detection composition including an oligonucleotide comprising the quencher or azo compound.
Oligomer synthesis contexts using cleavable/oligomer-synthesis support and specified protected functional groups as described in the disclosure.
Binding quencher 570 to oligonucleotides and evaluating quenching performance by emission intensity measurements and RT-PCR.
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