CA2162382A1 - Intercalators having affinity for dna and methods of use - Google Patents

Intercalators having affinity for dna and methods of use

Info

Publication number
CA2162382A1
CA2162382A1 CA002162382A CA2162382A CA2162382A1 CA 2162382 A1 CA2162382 A1 CA 2162382A1 CA 002162382 A CA002162382 A CA 002162382A CA 2162382 A CA2162382 A CA 2162382A CA 2162382 A1 CA2162382 A1 CA 2162382A1
Authority
CA
Canada
Prior art keywords
moieties
moiety
intercalator
compounds
flow cytometry
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002162382A
Other languages
French (fr)
Other versions
CA2162382C (en
Inventor
Christopher Bieniarz
Jeffrey Bruce Huff
Denis R. Henrard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Abbott Laboratories
Original Assignee
Christopher Bieniarz
Jeffrey Bruce Huff
Denis R. Henrard
Abbott Laboratories
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Christopher Bieniarz, Jeffrey Bruce Huff, Denis R. Henrard, Abbott Laboratories filed Critical Christopher Bieniarz
Publication of CA2162382A1 publication Critical patent/CA2162382A1/en
Application granted granted Critical
Publication of CA2162382C publication Critical patent/CA2162382C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/14—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C07D221/12—Phenanthridines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Intercalator compounds are provided which are comprised of intercalator moieties, or substituted intercalator moieties, having one or more functionalized chains, or moieties, and which compounds provide a high affinity for binding to the DNA molecule and show reduced self-quenching, while providing superior transport kinetics. The compounds have been found to provide enhanced fluorescence when bound to a DNA molecule within a fluorescent flow cytometry environment which is about eight to ten times brighter in fluorescence than "bis"
structure conventional intercalating agents and other known intercalating agents utilized in flow cytometry environment. The intercalator compounds comprise an I moiety bonded to one or more T moieties, said T moieties, when more than one said T moiety are present, are the same or different from one another, said compound having a formula I-(T)m wherein m is an integer from 1 to 5;
wherein said 1 moiety is selected from the group consisting of: (see formula I); said T moiety is selected from the group consisting of:
(see formula II).
CA002162382A 1993-06-30 1994-06-23 Intercalators having affinity for dna and methods of use Expired - Fee Related CA2162382C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US8628593A 1993-06-30 1993-06-30
US08/086,285 1993-06-30
PCT/US1994/007130 WO1995001341A1 (en) 1993-06-30 1994-06-23 Intercalators having affinity for dna and methods of use

Publications (2)

Publication Number Publication Date
CA2162382A1 true CA2162382A1 (en) 1995-01-12
CA2162382C CA2162382C (en) 2006-04-11

Family

ID=22197554

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002162382A Expired - Fee Related CA2162382C (en) 1993-06-30 1994-06-23 Intercalators having affinity for dna and methods of use

Country Status (8)

Country Link
US (1) US5582984A (en)
EP (3) EP1411047A1 (en)
JP (1) JP3856463B2 (en)
AT (1) ATE264307T1 (en)
CA (1) CA2162382C (en)
DE (2) DE69435240D1 (en)
ES (2) ES2218527T3 (en)
WO (1) WO1995001341A1 (en)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5861247A (en) * 1996-01-26 1999-01-19 University Of Chicago Rapid method to detect duplex formation in sequencing by hybridization methods
SE506700C2 (en) * 1996-05-31 1998-02-02 Mikael Kubista Probe and Methods for Analysis of Nucleic Acid
US5730849A (en) * 1996-09-30 1998-03-24 Bio-Rad Laboratories, Inc. High sensitivity dyes as stains for RNA bands in denaturing gels
US7087148B1 (en) 1998-06-23 2006-08-08 Clinical Micro Sensors, Inc. Binding acceleration techniques for the detection of analytes
US6290839B1 (en) 1998-06-23 2001-09-18 Clinical Micro Sensors, Inc. Systems for electrophoretic transport and detection of analytes
US6761816B1 (en) 1998-06-23 2004-07-13 Clinical Micro Systems, Inc. Printed circuit boards with monolayers and capture ligands
US7312087B2 (en) * 2000-01-11 2007-12-25 Clinical Micro Sensors, Inc. Devices and methods for biochip multiplexing
US6673568B1 (en) 1999-10-25 2004-01-06 Genprime, Inc. Method and apparatus for prokaryotic and eukaryotic cell quantitation
US6787302B2 (en) * 1999-10-25 2004-09-07 Genprime, Inc. Method and apparatus for prokaryotic and eukaryotic cell quantitation
KR20020070328A (en) 1999-12-21 2002-09-05 오르토-클리니칼 다이아그노스틱스, 인코포레이티드 Detection of nucleic acids
WO2002008454A2 (en) * 2000-07-24 2002-01-31 Genprime, Inc. Method and device for viable and nonviable prokaryotic and eukaryotic cell quantitation
JP3975167B2 (en) 2001-01-08 2007-09-12 アプレーラ コーポレイション Dendritic chemiluminescent substrate
JP4628594B2 (en) * 2001-06-25 2011-02-09 昭和電工株式会社 Organic light emitting device and light emitting material
US9261460B2 (en) 2002-03-12 2016-02-16 Enzo Life Sciences, Inc. Real-time nucleic acid detection processes and compositions
US9353405B2 (en) 2002-03-12 2016-05-31 Enzo Life Sciences, Inc. Optimized real time nucleic acid detection processes
US7166478B2 (en) * 2002-03-12 2007-01-23 Enzo Life Sciences, Inc., C/O Enzo Biochem, Inc. Labeling reagents and labeled targets, target labeling processes and other processes for using same in nucleic acid determinations and analyses
GB0327524D0 (en) 2003-11-26 2003-12-31 Univ Glasgow Heterocyclic aromatic compounds
DE602005027811D1 (en) * 2004-02-13 2011-06-16 Dsm Ip Assets Bv IONIC UV-A SUN PROTECTION AGENTS AND COMPOSITIONS CONTAINING THEM
US20100003679A1 (en) * 2006-06-09 2010-01-07 University Of Miami Assessment of cellular composition and fractional viability and uses thereof
US7943320B2 (en) * 2008-12-30 2011-05-17 Canon U.S. Life Sciences, Inc. Unsymmetrical cyanine dyes for high resolution nucleic acid melting analysis
SG174571A1 (en) * 2009-03-25 2011-10-28 Univ Nanyang Tech A fluidic apparatus and/or method for differentiating viable cells
WO2013189043A1 (en) * 2012-06-20 2013-12-27 大连理工大学 Green fluorescent cyanine dyes, preparation method and uses thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4665184A (en) * 1983-10-12 1987-05-12 California Institute Of Technology Bifunctional molecules having a DNA intercalator or DNA groove binder linked to ethylene diamine tetraacetic acid
US4683195A (en) * 1986-01-30 1987-07-28 Cetus Corporation Process for amplifying, detecting, and/or-cloning nucleic acid sequences
US4912208A (en) 1987-06-29 1990-03-27 Abbott Laboratories Fluorophores for encapsulation into liposomes
US4994385A (en) 1987-10-30 1991-02-19 Abbott Laboratories Heterobifunctional coupling agents
US5002883A (en) 1987-10-30 1991-03-26 Abbott Laboratories Covalent attachment of antibodies and antigens to solid phases using extended length heterobifunctional coupling agents
US5053520A (en) 1988-09-22 1991-10-01 Abbott Laboratories Heterobifunctional maleimido containing coupling agents
US5063109A (en) 1988-10-11 1991-11-05 Abbott Laboratories Covalent attachment of antibodies and antigens to solid phases using extended length heterobifunctional coupling agents
US5312921A (en) * 1990-03-14 1994-05-17 Regents Of The University Of California Dyes designed for high sensitivity detection of double-stranded DNA
GB9122525D0 (en) * 1991-10-23 1991-12-04 Isis Innovation Dna bis-intercalators

Also Published As

Publication number Publication date
ES2331813T3 (en) 2010-01-15
JPH09500871A (en) 1997-01-28
EP1411047A1 (en) 2004-04-21
DE69433712T2 (en) 2005-04-14
ATE264307T1 (en) 2004-04-15
EP1792897B1 (en) 2009-09-16
DE69433712D1 (en) 2004-05-19
DE69435240D1 (en) 2009-10-29
WO1995001341A1 (en) 1995-01-12
EP1792897A3 (en) 2007-06-13
JP3856463B2 (en) 2006-12-13
EP0706515B1 (en) 2004-04-14
ES2218527T3 (en) 2004-11-16
CA2162382C (en) 2006-04-11
EP0706515A1 (en) 1996-04-17
EP1792897A2 (en) 2007-06-06
US5582984A (en) 1996-12-10

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Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20140625