JP2005537480A5 - - Google Patents
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- JP2005537480A5 JP2005537480A5 JP2004532561A JP2004532561A JP2005537480A5 JP 2005537480 A5 JP2005537480 A5 JP 2005537480A5 JP 2004532561 A JP2004532561 A JP 2004532561A JP 2004532561 A JP2004532561 A JP 2004532561A JP 2005537480 A5 JP2005537480 A5 JP 2005537480A5
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OZCULFZQSHFJNI-UHFFFAOYSA-N 4-benzoylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(=O)C1=CC=CC=C1 OZCULFZQSHFJNI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Description
実施例３
オリゴヌクレオチド誘導体化光ポリマーの製造および評価
（ａ）４−ベンゾイルベンゾイルクロリド（ＢＢＡ−Ｃ１）の製造
４−ベンゾイル安息香酸（ＢＢＡ）１．０ｋｇ（４．４２モル）を還流冷却器および吊り攪拌器（overhead stirrer）を備えた乾燥５リットルモルトンフラスコに加え、続けて塩化チオニル６４５ｍｌ（８．８４モル）およびトルエン７２５ｍｌを加えた。次いで、ジメチルホルムアミド３．５ｍｌを加え、４時間加熱還流した。冷却後、溶媒を減圧下で除去し、残存塩化チオニルをトルエン３×５００ｍｌを用いて３度の蒸発により除去する。生成物をトルエン／ヘキサン（１／４）から再結晶化し、真空オーブン中での乾燥後、９８８ｇ（収率９１％）を得た。生成物の融点は、９２〜９４℃であった。８０ＭＨｚ（1ＨＮＭＲ（ＣＤＣｌ3））での核磁気共鳴（ＮＭＲ）分析は、所望の生成物と一致した：芳香族プロトン７．２０−８．２５（ｍ、９Ｈ）。化学シフト値はすべて、テトラメチルシラン内部標準から低磁場側のｐｐｍである。例えば実施例３（ｃ）に記載される光活性可能なポリマーの合成に用いられるモノマーの製造における使用のため、または例えば実施例１（ａ）に記載されるヘテロ二官能性化合物のため、最終化合物を保存した。
オリゴヌクレオチド誘導体化光ポリマーの製造および評価
（ａ）４−ベンゾイルベンゾイルクロリド（ＢＢＡ−Ｃ１）の製造
４−ベンゾイル安息香酸（ＢＢＡ）１．０ｋｇ（４．４２モル）を還流冷却器および吊り攪拌器（overhead stirrer）を備えた乾燥５リットルモルトンフラスコに加え、続けて塩化チオニル６４５ｍｌ（８．８４モル）およびトルエン７２５ｍｌを加えた。次いで、ジメチルホルムアミド３．５ｍｌを加え、４時間加熱還流した。冷却後、溶媒を減圧下で除去し、残存塩化チオニルをトルエン３×５００ｍｌを用いて３度の蒸発により除去する。生成物をトルエン／ヘキサン（１／４）から再結晶化し、真空オーブン中での乾燥後、９８８ｇ（収率９１％）を得た。生成物の融点は、９２〜９４℃であった。８０ＭＨｚ（1ＨＮＭＲ（ＣＤＣｌ3））での核磁気共鳴（ＮＭＲ）分析は、所望の生成物と一致した：芳香族プロトン７．２０−８．２５（ｍ、９Ｈ）。化学シフト値はすべて、テトラメチルシラン内部標準から低磁場側のｐｐｍである。例えば実施例３（ｃ）に記載される光活性可能なポリマーの合成に用いられるモノマーの製造における使用のため、または例えば実施例１（ａ）に記載されるヘテロ二官能性化合物のため、最終化合物を保存した。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/233,071 US20030082604A1 (en) | 2000-09-27 | 2002-08-30 | High density arrays |
| PCT/US2003/009795 WO2004020085A1 (en) | 2002-08-30 | 2003-04-01 | High density arrays |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005537480A JP2005537480A (ja) | 2005-12-08 |
| JP2005537480A5 true JP2005537480A5 (ja) | 2006-06-01 |
Family
ID=31977141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004532561A Pending JP2005537480A (ja) | 2002-08-30 | 2003-04-01 | 高密度アレイ |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20030082604A1 (ja) |
| EP (1) | EP1534420A1 (ja) |
| JP (1) | JP2005537480A (ja) |
| AU (1) | AU2003222130A1 (ja) |
| CA (1) | CA2495922A1 (ja) |
| WO (1) | WO2004020085A1 (ja) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7351575B2 (en) * | 2000-11-08 | 2008-04-01 | Surface Logix, Inc. | Methods for processing biological materials using peelable and resealable devices |
| AT501110A1 (de) * | 2003-09-16 | 2006-06-15 | Upper Austrian Res Gmbh | Arrays zur bindung von molekülen |
| EP2290073A3 (en) | 2004-05-28 | 2011-08-31 | Asuragen, Inc. | Methods and compositions involving microRNA |
| 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 |
| JP2006118920A (ja) * | 2004-10-20 | 2006-05-11 | Institute Of Physical & Chemical Research | 相互作用観察方法 |
| EP2302055B1 (en) | 2004-11-12 | 2014-08-27 | Asuragen, Inc. | Methods and compositions involving miRNA and miRNA inhibitor molecules |
| WO2006135782A2 (en) | 2005-06-10 | 2006-12-21 | Applera Corporation | Method and system for multiplex genetic analysis |
| WO2008036776A2 (en) | 2006-09-19 | 2008-03-27 | Asuragen, Inc. | Mir-15, mir-26, mir -31,mir -145, mir-147, mir-188, mir-215, mir-216 mir-331, mmu-mir-292-3p regulated genes and pathways as targets for therapeutic intervention |
| US20090131348A1 (en) | 2006-09-19 | 2009-05-21 | Emmanuel Labourier | Micrornas differentially expressed in pancreatic diseases and uses thereof |
| DE102006059095A1 (de) * | 2006-12-08 | 2008-06-12 | Technische Universität Dresden | Microarray, Verfahren und Kit zum Nachweis von Viren |
| WO2009036332A1 (en) | 2007-09-14 | 2009-03-19 | Asuragen, Inc. | Micrornas differentially expressed in cervical cancer and uses thereof |
| US8796184B2 (en) * | 2008-03-28 | 2014-08-05 | Sentilus, Inc. | Detection assay devices and methods of making and using the same |
| WO2009137807A2 (en) | 2008-05-08 | 2009-11-12 | Asuragen, Inc. | Compositions and methods related to mirna modulation of neovascularization or angiogenesis |
| US20100056382A1 (en) * | 2008-05-30 | 2010-03-04 | Sussman Michael R | Dna millichip |
| EP2542678B1 (en) | 2010-03-04 | 2017-04-12 | InteRNA Technologies B.V. | A MiRNA MOLECULE DEFINED BY ITS SOURCE AND ITS THERAPEUTIC USES IN CANCER ASSOCIATED WITH EMT |
| US8974651B2 (en) | 2010-04-17 | 2015-03-10 | C.C. Imex | Illuminator for visualization of fluorophores |
| EP2591106A1 (en) | 2010-07-06 | 2013-05-15 | InteRNA Technologies B.V. | Mirna and its diagnostic and therapeutic uses in diseases or conditions associated with melanoma, or in diseases or conditions associated with activated braf pathway |
| BR112013012265A2 (pt) | 2010-11-17 | 2016-08-02 | Asuragen Inc | mirnas como biomarcadores para distinguir neoplasmas de tireoide benignos de malignos |
| EP2474617A1 (en) | 2011-01-11 | 2012-07-11 | InteRNA Technologies BV | Mir for treating neo-angiogenesis |
| EP2681566A2 (en) | 2011-02-28 | 2014-01-08 | University of Iowa Research Foundation | Anti-müllerian hormone changes in pregnancy and prediction ofadverse pregnancy outcomes and gender |
| WO2013040251A2 (en) | 2011-09-13 | 2013-03-21 | Asurgen, Inc. | Methods and compositions involving mir-135b for distinguishing pancreatic cancer from benign pancreatic disease |
| WO2013063519A1 (en) | 2011-10-26 | 2013-05-02 | Asuragen, Inc. | Methods and compositions involving mirna expression levels for distinguishing pancreatic cysts |
| WO2013063544A1 (en) | 2011-10-27 | 2013-05-02 | Asuragen, Inc. | Mirnas as diagnostic biomarkers to distinguish benign from malignant thyroid tumors |
| WO2014007623A1 (en) | 2012-07-03 | 2014-01-09 | Interna Technologies B.V. | Diagnostic portfolio and its uses |
| WO2014055117A1 (en) | 2012-10-04 | 2014-04-10 | Asuragen, Inc. | Diagnostic mirnas for differential diagnosis of incidental pancreatic cystic lesions |
| US9758835B2 (en) | 2013-03-15 | 2017-09-12 | Baylor Research Institute | Ulcerative colitis (UC)-associated colorectal neoplasia markers |
| CA2907377A1 (en) | 2013-03-15 | 2014-09-18 | Baylor Research Institute | Tissue and blood-based mirna biomarkers for the diagnosis, prognosis and metastasis-predictive potential in colorectal cancer |
| US9944992B2 (en) | 2013-03-15 | 2018-04-17 | The University Of Chicago | Methods and compositions related to T-cell activity |
| US9835587B2 (en) | 2014-04-01 | 2017-12-05 | C.C. Imex | Electrophoresis running tank assembly |
| CN111566212A (zh) | 2017-11-03 | 2020-08-21 | 因特尔纳技术有限公司 | miRNA分子，等同物，安塔够妙或其来源用于治疗和/或诊断与神经元缺陷相关的病症和/或疾病或用于神经元生成和/或再生 |
| WO2019104155A2 (en) | 2017-11-22 | 2019-05-31 | The University Of Chicago | Chemical probe-dependent evaluation of protein activity and uses thereof |
| CN112218708B (zh) * | 2018-05-15 | 2023-06-16 | 生物复制有限公司 | 微阵列变换器 |
| EP3947727A4 (en) | 2019-04-05 | 2023-01-04 | Board of Regents, The University of Texas System | METHODS AND APPLICATIONS OF CELL BARCODING |
| JP7566775B2 (ja) | 2019-04-12 | 2024-10-15 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 筋肉量及び酸化的代謝を増加させるための組成物及び方法 |
| WO2024028794A1 (en) | 2022-08-02 | 2024-02-08 | Temple Therapeutics BV | Methods for treating endometrial and ovarian hyperproliferative disorders |
| WO2025248505A1 (en) | 2024-05-31 | 2025-12-04 | Wayne State University | Methods for treating endometrial and ovarian hyperproliferative disorders |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002582A (en) * | 1982-09-29 | 1991-03-26 | Bio-Metric Systems, Inc. | Preparation of polymeric surfaces via covalently attaching polymers |
| GB8314523D0 (en) * | 1983-05-25 | 1983-06-29 | Lowe C R | Diagnostic device |
| US6589726B1 (en) * | 1991-09-04 | 2003-07-08 | Metrigen, Inc. | Method and apparatus for in situ synthesis on a solid support |
| CA2124087C (en) * | 1991-11-22 | 2002-10-01 | James L. Winkler | Combinatorial strategies for polymer synthesis |
| US5795714A (en) * | 1992-11-06 | 1998-08-18 | Trustees Of Boston University | Method for replicating an array of nucleic acid probes |
| RU2041261C1 (ru) * | 1993-08-11 | 1995-08-09 | Институт молекулярной биологии им.В.А.Энгельгардта РАН | Способ изготовления матрицы для детектирования мисматчей |
| US5807522A (en) * | 1994-06-17 | 1998-09-15 | The Board Of Trustees Of The Leland Stanford Junior University | Methods for fabricating microarrays of biological samples |
| US6147205A (en) * | 1995-12-15 | 2000-11-14 | Affymetrix, Inc. | Photocleavable protecting groups and methods for their use |
| US6057100A (en) * | 1996-06-07 | 2000-05-02 | Eos Biotechnology, Inc. | Oligonucleotide arrays |
| US6406845B1 (en) * | 1997-05-05 | 2002-06-18 | Trustees Of Tuft College | Fiber optic biosensor for selectively detecting oligonucleotide species in a mixed fluid sample |
| US6121027A (en) * | 1997-08-15 | 2000-09-19 | Surmodics, Inc. | Polybifunctional reagent having a polymeric backbone and photoreactive moieties and bioactive groups |
| WO2000036398A2 (de) * | 1998-12-14 | 2000-06-22 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Verfahren und vorrichtungen zur erfassung optischer eigenschaften, insbesondere von lumineszenz-reaktionen und brechungsverhalten, von auf einem träger direkt oder indirekt gebundenen molekülen |
| AU2001288960A1 (en) * | 2000-09-27 | 2002-04-08 | Surmodics, Inc. | High density arrays |
-
2002
- 2002-08-30 US US10/233,071 patent/US20030082604A1/en not_active Abandoned
-
2003
- 2003-04-01 JP JP2004532561A patent/JP2005537480A/ja active Pending
- 2003-04-01 AU AU2003222130A patent/AU2003222130A1/en not_active Abandoned
- 2003-04-01 WO PCT/US2003/009795 patent/WO2004020085A1/en not_active Ceased
- 2003-04-01 EP EP03718117A patent/EP1534420A1/en not_active Withdrawn
- 2003-04-01 CA CA002495922A patent/CA2495922A1/en not_active Abandoned
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