WO1992001699A1 - Pt-CONTAINING COMPOUND, PROCESS FOR ITS PREPARATION, AND APPLICATION OF SUCH COMPOUNDS - Google Patents
Pt-CONTAINING COMPOUND, PROCESS FOR ITS PREPARATION, AND APPLICATION OF SUCH COMPOUNDS Download PDFInfo
- Publication number
- WO1992001699A1 WO1992001699A1 PCT/NL1991/000126 NL9100126W WO9201699A1 WO 1992001699 A1 WO1992001699 A1 WO 1992001699A1 NL 9100126 W NL9100126 W NL 9100126W WO 9201699 A1 WO9201699 A1 WO 9201699A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fluorescein
- nhch
- ethylenediamine
- formula
- compound according
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6816—Hybridisation assays characterised by the detection means
Definitions
- Pt-containing compound process for its preparation, and application of such compounds.
- Pt-containing compounds are known from Reedijk, J. Struct. Bonding (Berlin), 67: 53-72.
- This article describes the anti-tumor compound ci ⁇ - Pt(NH 3 ) 2 Cl 2 , which compound has a high affinity for (amongst others) proteins and DNA molecules and particularly it appears that such a compound has a marked affinity for the N7-nitrogen atom in the purine bases Guanine and Adenine, as well as for sulphur groups in macromolecules.
- onochlorinated platinum compounds like Pt(diene)Cl appear to keep their DNA affinity but they do not form cross-links and interfere only slightly with the base pairing of complementary DNA strands, and are as such not anti-tumor active.
- Labelling by direct chemical coupling, like photo- biotin, AAF, mercury, sulfone groups.
- Application of such labels brings along a number of problems, which are particularly related to the complexity of the labelling procedure, the sometimes limited length of the synthetic oligonucleotides which are to be labelled, to use of health-injuring compounds and the stability of the label, when it is bound to the nucleic acid.
- the invention now contemplates providing platinum- containing compounds, in the application of which the above- mentioned disadvantages are effectively removed.
- the invention provides a compound with the formula ⁇ Pt"(w) (x) (y) (z) ⁇ or ⁇ Pt IV (u) (v) (w) (x) (y) (z) ⁇ with the structural formula 1 or 2 respectively of the formula sheet, in which u, v, w, x, y and z represent whether or not the same whether or not interconnected ligand ⁇ , from which at least one is a leaving ligand and at least one of the remaining ligands represents a detectable marker group.
- Such a compound which is novel per se, and on the one side is provided with a directly or indirectly detectable marker group, as for instance a hapten, fluorescein or rhodamine and on the other side is provided with a suitable leaving group, is an especially suitable and novel DNA label with the general indication PtM (Pt stands for platinum and M stands for marker group) with unique properties.
- the thus labelled DNA may be separated from the redundant compound with the formula 1 or 2 of the formula sheet by alcohol precipitation.
- An important advantage is, that the thus labelled DNA may be detected immediately after hybridization by means of a fluorescence microscope or indirectly with one of the known immunohistochemical staining techniques.
- a radioactive ( 14 C or 35 S)-platinum- containing compound according to the invention may be applied as simple and fast (non-enzymatic) labelling of probes, followed by direct detection by means of autoradiography.
- Another important new application of the probes labelled with the present compounds is in situ hybridization in the electron microscope whereby the high mass of the platinum atom in the compound according to the invention takes care for a direct probe-specific local increase of the electron density.
- leaving ligand (CH 3 ) 2 SO, H 2 0 or Cl appears to be especially suitable according to the invention.
- a special preference merits fluorescein isothiocyanate (FITC) or tetramethyl rhodamine isothiocyanate (TR ⁇ TC) .
- FITC fluorescein isothiocyanate
- TR ⁇ TC tetramethyl rhodamine isothiocyanate
- a very suitable compound according to the invention is ⁇ Pt(ethylenediamine) (Me 2 S0) (fluorescein-NH(CS)-NHCH 3 ) ⁇ , in the following abbreviated as PtF.
- novel compounds according to the invention are especially suitable for virus diagnostic purposes, bacteria diagnostic purposes, for detection of genetic deviations, detection of gene expression etc.
- virus strains or subtypes may be distinguished from each other by DNA/RNA probes. Detection methods using labelled DNA or RNA probes appear to be able to solve these problems. Much progress has been made in the diagnosis of both DNA and RNA viruses. The advantage of these methods is that immediately the patient material (smears, samples of blister, nose and other fluids, tissue sections etc.) may be tested on the presence of virus DNA/RNA. Also retrospective studies have already provided important information about viral causes of mortality etc.
- the invention comprises a process for the preparation of Pt-containing compounds according to the invention with the formula ⁇ Pt XI (w) (x) (y) (z) ⁇ or
- the invention extends to a diagnostic kit for use in the detection of viruses, bacteria, parasites, genetic deviations, gene expression, which kit comprises a Pt- containing compound according to the invention.
- PtF ⁇ Pt(ethylenediamine)Cl(fluorescein-NH(CS)NHCH 3 ) ⁇ , abbreviated PtF.
- the reaction may be carried out at an analogous manner with as starting material the one as mentioned above, provided that fluorescein is replaced by for instance rhodamine, AMCA, biotin, digoxygenin or any other hapten, which may be modified in such a manner that therein is present a double-bounded sulphur (S) atom, a -SR group, a NR'R' * group or a nitrogen ring (-N-) , wherein R*R' ' are equal or not equal to each other and represent an organic residual group. (Also H is possible) . These S- or N-atoms serve as binding ligand for the platinum (Pt) atom.
- the dry PtF compound is dissolved at a concentration of 1 mg/ml in distilled water, which has been brought at a pH of 9-10 with NaOH.
- DNA single or double stranded
- RNA at an arbitrary concentration (for instance 100 ⁇ g/ml) was taken up in a low-salt buffer with a pH of about 8 (for instance 10 mM TRIS-HC1) and possibly fragmented by ultrasonication.
- the obtained pellet was washed in 90% ethanol and the nucleic acid labelled with the PtF was dissolved at the desired concentration at an arbitrary buffer (for instance lO TRIS- HC1, a pH of 7.5, 0.3 mM EDTA) .
- an arbitrary buffer for instance lO TRIS- HC1, a pH of 7.5, 0.3 mM EDTA
- Human papilloma virus cannot be cultured, but some subtypes (HPV 16/18) are positively connected with the origin of malignant tumors of amongst others the cervix and the penis.
- the presence of the risk bearing type papilloma virus may be shown very specifically by means of a direct fluorescence procedure or an indirect immunohistochemical procedure with anti-PtM antibodies.
- Example IV Human papilloma virus cannot be cultured, but some subtypes (HPV 16/18) are positively connected with a large chance on the development of malignant tumors on cervix or penis. Further, probes are developed for amongst others the detection of DNA (Vaccinia, Herpes simplex (HSV1/2, Epstein Barr, and adenovirus) and RNA viruses (Rota virus, influenza A, Cocksackie B) . Until present the diagnosis of acute infection with Hepatitis B virus is only possible by inoculation of chimpanzees (i) , for the virus cannot be cultured in human cells.
- DNA Vaccinia, Herpes simplex (HSV1/2, Epstein Barr, and adenovirus
- RNA viruses Rosta virus, influenza A, Cocksackie B
- Varicella zoster virus too, is very difficult to culture: it lasts 5-14 days, before a culture may be assessed. Moreover the virus is very labile and may become inactivated during transport. A negative test is therefore no proof of absence of the illness. Over and above a VZV infection is on morphological grounds indistinguishable from infections with Herpes simplex virus. Even commercially available antisera do not give an answer in immunohistochemical tests.
- Cytomegalo virus is very laboriously cultured; diagnoses within a week's time are impossible, within 6 weeks no exception. CMV infections form an important source of complications in transplant-patients and in patients with reduced defence (AIDS) . A good monitoring of these patients is essential. In the above-mentioned cases a, b and c, which figure as only some of the many possibilities of examples of virus diagnostics, diagnostics may be considerably simplified and accelerated by the application of hybridization techniques with PtM-labelled probes.
- DNA of Chlamydia trachomatis may be detected in for instance a sandwich assay, or by means of an in situ hybridization.
- the hybridization technique with PtM probes offers the possibility for prenatal diagnostics of congenital deviations in for instance amniotic fluid punctates and chorionbioses. Postnatal detection of deviations (for instance malignities) is also possible, as well as extension of HLA typification for diagnosis of HLA associated illnesses.
- Restriction fragment polymorfisms Every human genome will fall apart, when treated with restriction enzymes, in a large number of specific fragments: the restriction fragments. If by a mutation the base sequence changes on a site where a restriction enzyme attacks, will this lead to the development of aberrant fragments. These fragments may be detected by suitable (PtM labelled) probes by means of DNA blotting methods (for instance in sickle cell anaemia, Duchenne muscle dystrophia, cystic fibrosis, Huntingdon chorea) .
- Immediate detection of aberrant DNA with synthetic oligonucleotide probes may take place when the base sequence belonging to a DNA deviation is known ( ⁇ -thalassemia, anti- thrombin III deficiency, grow hormones deficiency, haemo ⁇ philia B, PKU .... etc.).
- Detection of chromosome changes as translocations, deletes, inversions and duplications in the human karyotype may be detected by- eans of in situ hybridization followed by direct PtF fluorescence, or by Southern blotting of restriction fragments.
- Detection of gene expression The visualization of the presence of a cellular anti ⁇ gen using immunoche ical techniques does not prove that at that moment the relative gene are expressed. Neither does this indicate whether the shown product has an intra- or extracellular origin. Detection of mRNA within a cell gives direct information about the expression of genes. This information may provide data on cell functioning, but may also be of assistance in diagnostics.
- RISH or blotting may be applied in the diagnosis of cancer by means of detection of specific gene transcripts (for instance calcitonin mRNA in thyroid gland metastase ⁇ , oncogene expression in malignant tumors) , or the loss of germ line bands (loss of heterozygoty) or gene rearrangement (lymphomas) .
- specific gene transcripts for instance calcitonin mRNA in thyroid gland metastase ⁇ , oncogene expression in malignant tumors
- loss of germ line bands loss of heterozygoty
- gene rearrangement lymphomas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Packages (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/975,586 US5580990A (en) | 1990-07-19 | 1991-07-16 | Pt-containing compound, process for its preparation, and application of such compounds |
EP91913437A EP0539466B1 (en) | 1990-07-19 | 1991-07-16 | Pt-CONTAINING COMPOUND, PROCESS FOR ITS PREPARATION, AND APPLICATION OF SUCH COMPOUNDS |
DE69123251T DE69123251T2 (de) | 1990-07-19 | 1991-07-16 | Platinenthaltende verbindung, verfahren zu deren herstellung sowie deren verwendung |
JP51258291A JP3512792B2 (ja) | 1990-07-19 | 1991-07-16 | Pt含有化合物、その合成方法及びこれらの化合物の応用 |
GR970400266T GR3022581T3 (en) | 1990-07-19 | 1997-02-19 | Pt-CONTAINING COMPOUND, PROCESS FOR ITS PREPARATION, AND APPLICATION OF SUCH COMPOUNDS |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL9001639A NL9001639A (nl) | 1990-07-19 | 1990-07-19 | Pt-houdende verbinding, werkwijze voor de bereiding ervan, alsmede toepassing van dergelijke verbindingen. |
NL9001639 | 1990-07-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992001699A1 true WO1992001699A1 (en) | 1992-02-06 |
Family
ID=19857433
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/NL1991/000126 WO1992001699A1 (en) | 1990-07-19 | 1991-07-16 | Pt-CONTAINING COMPOUND, PROCESS FOR ITS PREPARATION, AND APPLICATION OF SUCH COMPOUNDS |
Country Status (11)
Country | Link |
---|---|
US (1) | US5580990A (nl) |
EP (1) | EP0539466B1 (nl) |
JP (2) | JP3512792B2 (nl) |
AT (1) | ATE145403T1 (nl) |
AU (1) | AU8286391A (nl) |
DE (1) | DE69123251T2 (nl) |
DK (1) | DK0539466T3 (nl) |
ES (1) | ES2097213T3 (nl) |
GR (1) | GR3022581T3 (nl) |
NL (1) | NL9001639A (nl) |
WO (1) | WO1992001699A1 (nl) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996035696A1 (en) * | 1995-05-09 | 1996-11-14 | Kreatech Biotechnology B.V. | Methods for the production of platinum-based linkers between labels and bio-organic molecules, for labelling bio-organic molecules, for detecting biological substances of interest and diagnostic test kits |
WO1998015564A1 (en) * | 1996-10-08 | 1998-04-16 | Kreatech Biotechnology B.V. | Methods for labeling nucleotides, labeled nucleotides and useful intermediates |
FR2755146A1 (fr) * | 1996-10-28 | 1998-04-30 | Centre Nat Rech Scient | Procede de pontage selectif et irreversible d'oligonucleotides platines sur de l'arn et ses applications |
US5953060A (en) * | 1995-10-31 | 1999-09-14 | Imec Vzw | Method for reducing fixed pattern noise in solid state imaging devices |
EP1324352A2 (en) * | 2001-12-25 | 2003-07-02 | Fuji Xerox Co., Ltd. | Organic conductor |
US6825330B2 (en) | 2001-03-02 | 2004-11-30 | Stratagene California | Compositions and methods using platinum compounds for nucleic acid labeling |
WO2011153354A1 (en) | 2010-06-03 | 2011-12-08 | Cellay, Inc. | Methods and kits for in situ detection of nucleotide sequences |
WO2013090386A2 (en) | 2011-12-12 | 2013-06-20 | Cellay, Inc. | Methods and kits for room temperature in situ detection of a target nucleic acid in a biological sample |
WO2013105856A1 (en) | 2012-01-13 | 2013-07-18 | Apo-T B.V. | Aberrant cell-restricted immunoglobulins provided with a toxic moiety |
WO2014070460A1 (en) | 2012-10-31 | 2014-05-08 | Cellay, Inc. | Methods and kits for performing in situ hybridization |
WO2015069920A1 (en) | 2013-11-07 | 2015-05-14 | Cellay, Inc. | Methods and kits for detecting a prostate carcinoma and predicting disease outcomes for prostate cancers |
EP2944647A1 (en) | 2007-07-26 | 2015-11-18 | Cellay, Inc. | Highly visible chromosome-specific probes and related methods |
US11098115B2 (en) | 2011-09-29 | 2021-08-24 | Apo-T B.V. | Multi-specific binding molecules targeting aberrant cells |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19516196A1 (de) * | 1995-05-08 | 1996-11-14 | Boehringer Mannheim Gmbh | Verfahren zum quantitativen Nachweis von Nukleinsäuren |
US5753207A (en) * | 1995-08-21 | 1998-05-19 | Beth Israel Deaconess Medical Center, Inc. | Use of paramagnetic compounds to measure temperature and pH in vivo |
EP1192258A2 (en) * | 1999-06-16 | 2002-04-03 | Icos Corporation | Human poly(adp-ribose) polymerase 2 materials and methods |
EP2325263B1 (en) | 2000-09-29 | 2013-01-23 | Life Technologies Corporation | Modified carbocyanine dyes and their conjugates |
EP1705254A3 (en) * | 2001-03-02 | 2007-02-21 | Stratagene California | Compositions and methods using platinum for nucleic acid labeling |
DK1262778T3 (da) * | 2001-05-28 | 2008-02-18 | Kreatech Biotech Bv | Fremgangsmåde til differentieret mærkning ved anvendelse af platinkomplekser |
US20050014134A1 (en) * | 2003-03-06 | 2005-01-20 | West Jason Andrew Appleton | Viral identification by generation and detection of protein signatures |
EP2604621B1 (en) | 2003-05-01 | 2015-10-21 | Cornell Research Foundation, Inc. | Method and carrier complexes for delivering molecules to cells |
EP1644533A4 (en) * | 2003-07-02 | 2007-11-14 | Perkinelmer Las Inc | ANALYSIS AND METHOD OF MARKING AND DETECTING RNA MICROSEQUENCES AND SMALL INTERFERENCE RNA SEQUENCES |
US20050095602A1 (en) * | 2003-11-04 | 2005-05-05 | West Jason A. | Microfluidic integrated microarrays for biological detection |
US8911942B2 (en) | 2004-05-20 | 2014-12-16 | Quest Diagnostics Investments Incorporated | Single label comparative hybridization |
US7524672B2 (en) * | 2004-09-22 | 2009-04-28 | Sandia Corporation | Microfluidic microarray systems and methods thereof |
US7592139B2 (en) | 2004-09-24 | 2009-09-22 | Sandia National Laboratories | High temperature flow-through device for rapid solubilization and analysis |
US7569695B2 (en) * | 2005-05-24 | 2009-08-04 | Enzo Life Sciences, Inc. | Dyes for the detection or quantification of desirable target molecules |
US7737281B2 (en) * | 2005-05-24 | 2010-06-15 | Enzo Life Sciences, Inc. C/O Enzo Biochem, Inc. | Purine based fluorescent dyes |
US8357801B2 (en) | 2005-05-24 | 2013-01-22 | Enzo Life Sciences, Inc. | Labeling of target molecules, identification of organelles and other applications, novel compositions, methods and kits |
US8362250B2 (en) | 2005-05-24 | 2013-01-29 | Enzo Biochem, Inc. | Fluorescent dyes and compounds, methods and kits useful for identifying specific organelles and regions in cells of interest |
US20060292576A1 (en) * | 2005-06-23 | 2006-12-28 | Quest Diagnostics Investments Incorporated | Non-in situ hybridization method for detecting chromosomal abnormalities |
US8076074B2 (en) | 2005-11-29 | 2011-12-13 | Quest Diagnostics Investments Incorporated | Balanced translocation in comparative hybridization |
US7824858B2 (en) | 2006-01-23 | 2010-11-02 | Quest Diagnostics Investments Incorporated | Assay for mycobacterium avium/intracellulare nucleic acid |
US8163480B2 (en) * | 2006-10-05 | 2012-04-24 | Quest Diagnostics Investments Incorporated | Nucleic acid size detection method |
US8999634B2 (en) | 2007-04-27 | 2015-04-07 | Quest Diagnostics Investments Incorporated | Nucleic acid detection combining amplification with fragmentation |
US7507539B2 (en) | 2007-07-30 | 2009-03-24 | Quest Diagnostics Investments Incorporated | Substractive single label comparative hybridization |
US8093063B2 (en) * | 2007-11-29 | 2012-01-10 | Quest Diagnostics Investments Incorporated | Assay for detecting genetic abnormalities in genomic nucleic acids |
US9334281B2 (en) * | 2008-09-08 | 2016-05-10 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
US9250249B2 (en) | 2008-09-08 | 2016-02-02 | Enzo Biochem, Inc. | Autophagy and phospholipidosis pathway assays |
US8431416B2 (en) | 2009-04-01 | 2013-04-30 | Becton, Dickinson And Company | Reactive heterocycle-substituted 7-hydroxycoumarins and their conjugates |
EP2473563B1 (en) | 2009-08-31 | 2019-06-19 | Promega Corporation | Reactive cyanine compounds |
US9133343B2 (en) | 2009-11-30 | 2015-09-15 | Enzo Biochem, Inc. | Dyes and compositions, and processes for using same in analysis of protein aggregation and other applications |
US8974651B2 (en) | 2010-04-17 | 2015-03-10 | C.C. Imex | Illuminator for visualization of fluorophores |
US8623324B2 (en) | 2010-07-21 | 2014-01-07 | Aat Bioquest Inc. | Luminescent dyes with a water-soluble intramolecular bridge and their biological conjugates |
US9416153B2 (en) | 2011-10-11 | 2016-08-16 | Enzo Life Sciences, Inc. | Fluorescent dyes |
WO2013102096A1 (en) | 2011-12-30 | 2013-07-04 | Quest Diagnostics Investments Incorporated | Aptamers and diagnostic methods for detecting the egf receptor |
US9835587B2 (en) | 2014-04-01 | 2017-12-05 | C.C. Imex | Electrophoresis running tank assembly |
WO2015183988A1 (en) | 2014-05-28 | 2015-12-03 | Stealth Peptides International, Inc. | Therapeutic compositions including therapeutic small molecules and uses thereof |
WO2015183995A2 (en) | 2014-05-28 | 2015-12-03 | Stealth Peptides International, Inc. | Therapeutic compositions including frataxin, lactoferrin, and mitochondrial energy generating enzymes, and uses thereof |
US9957393B2 (en) | 2015-03-30 | 2018-05-01 | Enzo Biochem, Inc. | Monoazo dyes with cyclic amine as fluorescence quenchers |
US10449259B2 (en) | 2015-10-02 | 2019-10-22 | Cornell University | Enzyme-responsive peptide nanofiber compositions and uses thereof |
JP2019512573A (ja) | 2016-03-28 | 2019-05-16 | エーエーティー バイオクエスト インコーポレイテッド | ポリフルオレノ[4,5−cde]オキセピンコンジュゲート及び分析物検出方法におけるそれらの使用 |
CN110520157A (zh) | 2017-02-09 | 2019-11-29 | 纪念斯隆凯特琳癌症中心 | 抗-kir3dl1抗体 |
WO2019244107A1 (en) | 2018-06-21 | 2019-12-26 | Daiichi Sankyo Company, Limited | Compositions including cd3 antigen binding fragments and uses thereof |
CN115280147A (zh) | 2020-01-30 | 2022-11-01 | 阿特生物探索公司 | 可紫外激发的基于聚芴的缀合物及其在分析物检测方法中的用途 |
JP2024503658A (ja) | 2021-01-13 | 2024-01-26 | メモリアル スローン-ケタリング キャンサー センター | 抗dll3抗体-薬物コンジュゲート |
WO2022153194A1 (en) | 2021-01-13 | 2022-07-21 | Memorial Sloan Kettering Cancer Center | Antibody-pyrrolobenzodiazepine derivative conjugate |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4490543A (en) * | 1982-11-12 | 1984-12-25 | University Of Northern Iowa Foundation | Low toxicity radiation sensitizer |
EP0147665A1 (en) * | 1983-12-12 | 1985-07-10 | Molecular Diagnostics, Inc. | Nucleic acid probe, test method and reagent system for detecting a polynucleotide sequence and antibody therefor |
EP0186363A1 (en) * | 1984-12-10 | 1986-07-02 | Johnson Matthey, Inc., | Platinum complexes |
WO1989009598A1 (en) * | 1988-04-13 | 1989-10-19 | The University Of Vermont And State Agricultural C | Platinum-amine-sulfoxides as anti-tumor agents |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2422956A1 (fr) * | 1978-04-13 | 1979-11-09 | Pasteur Institut | Procede de detection et de caracterisation d'un acide nucleique ou d'une sequence de celui-ci, et reactif enzymatique pour la mise en oeuvre de ce procede |
US4376165A (en) * | 1978-06-22 | 1983-03-08 | Miles Laboratories, Inc. | Method of preparing an enzyme-labeled ligand for use in specific binding assays and the labeled conjugate produced thereby |
US4358535A (en) * | 1980-12-08 | 1982-11-09 | Board Of Regents Of The University Of Washington | Specific DNA probes in diagnostic microbiology |
US4711955A (en) * | 1981-04-17 | 1987-12-08 | Yale University | Modified nucleotides and methods of preparing and using same |
US5241060A (en) * | 1982-06-23 | 1993-08-31 | Enzo Diagnostics, Inc. | Base moiety-labeled detectable nucleatide |
US4687732A (en) * | 1983-06-10 | 1987-08-18 | Yale University | Visualization polymers and their application to diagnostic medicine |
US5175269A (en) * | 1984-01-30 | 1992-12-29 | Enzo Diagnostics, Inc. | Compound and detectable molecules having an oligo- or polynucleotide with modifiable reactive group |
-
1990
- 1990-07-19 NL NL9001639A patent/NL9001639A/nl not_active Application Discontinuation
-
1991
- 1991-07-16 JP JP51258291A patent/JP3512792B2/ja not_active Expired - Fee Related
- 1991-07-16 DE DE69123251T patent/DE69123251T2/de not_active Expired - Fee Related
- 1991-07-16 ES ES91913437T patent/ES2097213T3/es not_active Expired - Lifetime
- 1991-07-16 AT AT91913437T patent/ATE145403T1/de not_active IP Right Cessation
- 1991-07-16 EP EP91913437A patent/EP0539466B1/en not_active Expired - Lifetime
- 1991-07-16 AU AU82863/91A patent/AU8286391A/en not_active Abandoned
- 1991-07-16 WO PCT/NL1991/000126 patent/WO1992001699A1/en active IP Right Grant
- 1991-07-16 US US07/975,586 patent/US5580990A/en not_active Expired - Lifetime
- 1991-07-16 DK DK91913437.9T patent/DK0539466T3/da active
-
1997
- 1997-02-19 GR GR970400266T patent/GR3022581T3/el unknown
-
2003
- 2003-09-18 JP JP2003326524A patent/JP3947508B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4490543A (en) * | 1982-11-12 | 1984-12-25 | University Of Northern Iowa Foundation | Low toxicity radiation sensitizer |
EP0147665A1 (en) * | 1983-12-12 | 1985-07-10 | Molecular Diagnostics, Inc. | Nucleic acid probe, test method and reagent system for detecting a polynucleotide sequence and antibody therefor |
EP0186363A1 (en) * | 1984-12-10 | 1986-07-02 | Johnson Matthey, Inc., | Platinum complexes |
WO1989009598A1 (en) * | 1988-04-13 | 1989-10-19 | The University Of Vermont And State Agricultural C | Platinum-amine-sulfoxides as anti-tumor agents |
Non-Patent Citations (1)
Title |
---|
Canadian Journal of Chemistry, vol. 63, no. 9, September 1985, KG Campbell Corp., (CA), F.D. Rochon et al.: "Synthesis and nuclear magnetic resonance spectra of platinum compounds with thiourea derivatives", pages 2425-2429, see the whole article * |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU724320B2 (en) * | 1995-05-09 | 2000-09-14 | Kreatech Biotechnology B.V. | Methods for the production of platinum-based linkers between labels and bio-organic molecules, for labelling bio-organic molecules, for detecting biological substances of interest and diagnostic test kits |
WO1996035696A1 (en) * | 1995-05-09 | 1996-11-14 | Kreatech Biotechnology B.V. | Methods for the production of platinum-based linkers between labels and bio-organic molecules, for labelling bio-organic molecules, for detecting biological substances of interest and diagnostic test kits |
US5953060A (en) * | 1995-10-31 | 1999-09-14 | Imec Vzw | Method for reducing fixed pattern noise in solid state imaging devices |
US7217813B2 (en) | 1996-10-08 | 2007-05-15 | Kreatech Biotechnology B.V. | Methods for labeling nucleotides, labeled nucleotides and useful intermediates |
WO1998015564A1 (en) * | 1996-10-08 | 1998-04-16 | Kreatech Biotechnology B.V. | Methods for labeling nucleotides, labeled nucleotides and useful intermediates |
US6338943B1 (en) * | 1996-10-08 | 2002-01-15 | Kreatech Biotechnology B.V. | Methods for labeling nucleotides, labeled nucleotides and useful intermediates |
USRE40557E1 (en) * | 1996-10-08 | 2008-10-28 | Kreatech Biotechnology B.V. | Methods for labeling nucleotides, labeled nucleotides and useful intermediates |
FR2755146A1 (fr) * | 1996-10-28 | 1998-04-30 | Centre Nat Rech Scient | Procede de pontage selectif et irreversible d'oligonucleotides platines sur de l'arn et ses applications |
US6825330B2 (en) | 2001-03-02 | 2004-11-30 | Stratagene California | Compositions and methods using platinum compounds for nucleic acid labeling |
US7238794B2 (en) | 2001-12-25 | 2007-07-03 | Fuji Xerox Co., Ltd. | Organic conductor |
US7419818B2 (en) | 2001-12-25 | 2008-09-02 | Fuji Xerox Co., Ltd | Organic conductor |
EP1324352A2 (en) * | 2001-12-25 | 2003-07-02 | Fuji Xerox Co., Ltd. | Organic conductor |
EP1324352A3 (en) * | 2001-12-25 | 2007-04-18 | Fuji Xerox Co., Ltd. | Organic conductor |
EP2944647A1 (en) | 2007-07-26 | 2015-11-18 | Cellay, Inc. | Highly visible chromosome-specific probes and related methods |
WO2011153354A1 (en) | 2010-06-03 | 2011-12-08 | Cellay, Inc. | Methods and kits for in situ detection of nucleotide sequences |
US11098115B2 (en) | 2011-09-29 | 2021-08-24 | Apo-T B.V. | Multi-specific binding molecules targeting aberrant cells |
WO2013090386A2 (en) | 2011-12-12 | 2013-06-20 | Cellay, Inc. | Methods and kits for room temperature in situ detection of a target nucleic acid in a biological sample |
WO2013105856A1 (en) | 2012-01-13 | 2013-07-18 | Apo-T B.V. | Aberrant cell-restricted immunoglobulins provided with a toxic moiety |
US20130183307A1 (en) * | 2012-01-13 | 2013-07-18 | Johan Renes | Aberrant cell-restricted immunoglobulins provided with a toxic moiety |
EP3470434A1 (en) | 2012-01-13 | 2019-04-17 | Apo-T B.V. | Aberrant cell-restricted immunoglobulins provided with a toxic moiety |
US10946104B2 (en) | 2012-01-13 | 2021-03-16 | Apo-Tb.V. | Aberrant cell-restricted immunoglobulins provided with a toxic moiety |
WO2014070460A1 (en) | 2012-10-31 | 2014-05-08 | Cellay, Inc. | Methods and kits for performing in situ hybridization |
WO2015069920A1 (en) | 2013-11-07 | 2015-05-14 | Cellay, Inc. | Methods and kits for detecting a prostate carcinoma and predicting disease outcomes for prostate cancers |
Also Published As
Publication number | Publication date |
---|---|
DE69123251T2 (de) | 1997-05-28 |
ES2097213T3 (es) | 1997-04-01 |
JP2004129659A (ja) | 2004-04-30 |
GR3022581T3 (en) | 1997-05-31 |
JPH05508853A (ja) | 1993-12-09 |
US5580990A (en) | 1996-12-03 |
DE69123251D1 (de) | 1997-01-02 |
JP3947508B2 (ja) | 2007-07-25 |
EP0539466A1 (en) | 1993-05-05 |
DK0539466T3 (da) | 1997-05-05 |
EP0539466B1 (en) | 1996-11-20 |
NL9001639A (nl) | 1992-02-17 |
AU8286391A (en) | 1992-02-18 |
JP3512792B2 (ja) | 2004-03-31 |
ATE145403T1 (de) | 1996-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0539466B1 (en) | Pt-CONTAINING COMPOUND, PROCESS FOR ITS PREPARATION, AND APPLICATION OF SUCH COMPOUNDS | |
US6133038A (en) | Platinum-containing compounds methods for their preparation and applications thereof | |
EP0702729B9 (en) | Chemical process for amplifying and detecting nucleic acid sequences | |
EP0777674B1 (en) | Polynucleotide reagents having nonnucleotidic moieties, and associated methods of synthesis and use | |
AU700055B2 (en) | Rapid nucleic acid assay | |
US5869252A (en) | Method of multiplex ligase chain reaction | |
EP0230363A2 (en) | Process for labeling single-stranded nucleic acids and hybridization probes | |
US4996142A (en) | Non-radioactive nucleic acid hybridization probes | |
DK164407B (da) | Modificerede nucleotider og fremgangsmaader til deres fremstilling, fremgangsmaade til paavisning af et dobbeltstrenget polynucleotidduplex indeholdende et modificeret nucleotid, fremgangsmaade til bestemmelse af tilstedevaerelsen af et deoxyribonucleinsyremolekyle eller et ribonucleinsyremolekyle, fremgangsmaade til test af en bakterie, fremgangsmaade til diagnosticering af en genetisk forstyrrelse, fre | |
AU3942993A (en) | Method of multiplex ligase chain reaction | |
JP3495752B2 (ja) | 生標的個体の検出方法およびプローブ | |
JPH08501689A (ja) | 改良型の鎖置換アッセイおよびそれに有用な複合体 | |
EP0133473B1 (en) | In vivo labelling of polynucleotide sequences | |
JPH08501220A (ja) | Neisseriagonorrhoeae同定用の単離されたヌクレオチド配列 | |
US20050181430A1 (en) | Rapid nucleic acid assay | |
WO1995019449A1 (en) | Populations of non-adjacent hybridization probes | |
Webster et al. | Separation and characterization of transcriptionally active and inactive nuclear subfractions of AKR mouse embryo cells | |
WO1994002640A1 (en) | Multi reporter-labeled nucleic acid probes | |
US7981599B1 (en) | Non-nucleic acid probes, probe sets, methods and kits pertaining to the detection of individual human chromosomes X, Y, 1, 2, 3, 4, 6, 7, 8, 9, 10, 11, 12, 16, 17, 18 and 20 as 13/21 as a pair | |
JPH06507318A (ja) | 染色体構造および転位の検出方法 | |
WO1995002699A1 (en) | Analogues of reporter groups as backgroung reducers in hybridization assays | |
Kelker et al. | Nonradioactive DNA Hybridization: Application to Clinical Microbiology | |
Isa | Optimization and Application of Chromosome In Situ Suppression Hybridization. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AU BB BG BR CA CS FI HU JP KP KR LK MC MG MN MW NO PL RO SD SU US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE BF BJ CF CG CH CI CM DE DK ES FR GA GB GN GR IT LU ML MR NL SE SN TD TG |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1991913437 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1991913437 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: CA |
|
WWG | Wipo information: grant in national office |
Ref document number: 1991913437 Country of ref document: EP |