公开(公告)号：US09157917B2

公开(公告)日：2015-10-13

申请号：US13883067

申请日：2011-11-04

申请人： Lukas Wick ,  Urs Spitz ,  Christophe Weymuth ,  Günter Schabert ,  Thomas Mayer ,  Alexander Bayer

发明人： Lukas Wick ,  Urs Spitz ,  Christophe Weymuth ,  Günter Schabert ,  Thomas Mayer ,  Alexander Bayer

IPC分类号： C07D221/18 ,  C09B67/08 ,  G01N33/58 ,  C09B57/00 ,  C09B67/44 ,  C12Q1/04 ,  C12Q1/10 ,  C12Q1/34 ,  C12Q1/44

CPC分类号： G01N33/583 ,  C09B57/00 ,  C09B67/0083 ,  C12Q1/04 ,  C12Q1/10 ,  C12Q1/34 ,  C12Q1/44 ,  G01N2333/938

摘要： A novel type of dye systems comprises a selection of 10H-indolo[1,2-a]indole compounds (henceforth abbreviated as IO compounds) and (5H,7H)-indolo[1,2-a]quinoline compounds (henceforth abbreviated as IQ compounds) showing a solvatochromic effect and exhibiting strong fluorescence in a variety of materials such as polypropylene, polyethylene, oils, various solvents, emulsions. Also disclosed are various methods how the IO/IQ compounds can be administered, especially how they can be produced and administered in situ from a precursor, responding to external stimuli such as enzyme activity, temperature and so forth. The response of a precursor to external stimuli can also be used to determine the presence or absence of such stimuli.

摘要翻译： 一种新型染料体系包括10H-吲哚并[1,2-a]吲哚化合物（以下简称为IO化合物）和（5H，7H） - 吲哚并[1,2-a]喹啉化合物（以下简称为 IQ化合物），显示出溶剂化色素效应，并在各种材料如聚丙烯，聚乙烯，油，各种溶剂，乳液中表现出强烈的荧光。 还公开了如何施用IO / IQ化合物的各种方法，特别是如何从前体产生和原位施用，对外部刺激如酶活性，温度等进行响应。 前体对外部刺激的反应也可以用于确定这种刺激的存在或不存在。

公开(公告)号：US20140212905A1

公开(公告)日：2014-07-31

申请号：US14123861

申请日：2012-06-08

申请人： Urs Spitz ,  Lukas Wick ,  Günter Schabert

发明人： Urs Spitz ,  Lukas Wick ,  Günter Schabert

IPC分类号： C12Q1/34

CPC分类号： C12Q1/34 ,  C12Q1/04 ,  C12Q1/06 ,  C12Q1/10

摘要： A method for detection of beta-D-glucuronidase activity in a sample that comprises the steps of (i) providing a glucuronic acid ester compound of the general formula (I) wherein R1 is a C1-4 alkyl group, OR2 is a dye moiety, which is liberated after cleavage of the glycosidic bond; (ii) contacting said glucuronic acid ester compound with a material of said sample exhibiting hydrolytic activity towards glucuronic acid esters, thereby removing R1 and thus forming a sample containing an indicator compound suitable for the detection and/or measurement of beta-D-glucuronidase activity, and (iii) using said indicator to perform an assay requiring detection or measurement of beta-D-glucuronidase activity.

摘要翻译： 一种检测样品中β-D-葡糖醛酸糖苷酶活性的方法，包括以下步骤：（i）提供通式（I）的葡萄糖醛酸酯化合物，其中R 1是C 1-4烷基，OR 2是染料部分 ，其在糖苷键断裂后释放; （ii）使所述葡糖醛酸酯化合物与所述样品对葡萄糖醛酸酯显示出水解活性的物质接触，从而除去R1，从而形成含有适于检测和/或测量β-D-葡糖醛酸糖苷酶活性的指示剂化合物的样品 ，和（iii）使用所述指示剂进行需要检测或测量β-D-葡糖苷酸酶活性的测定。

公开(公告)号：US20120058503A1

公开(公告)日：2012-03-08

申请号：US13266707

申请日：2010-05-06

申请人： Urs Spitz ,  Lukas Wick ,  Alexander Bayer ,  Christophe Weymuth ,  Günter Schabert

发明人： Urs Spitz ,  Lukas Wick ,  Alexander Bayer ,  Christophe Weymuth ,  Günter Schabert

IPC分类号： C12Q1/04 ,  C09B69/00 ,  G01N21/78 ,  C12Q1/02 ,  C12Q1/37

CPC分类号： C07D209/36 ,  C07D209/70 ,  C07D487/04

摘要： A novel indicator platform comprises a plurality of 1H-lndol-3-yl indicator compounds that are capable of converting to a signalophore compound in response to an external stimulus. In one class of indicator compounds, the resulting signalophores are 2-benzylideneindoline compounds that are formed by an intermolecular Aldol-type process; in a further class of indicator compounds, the resulting signalophores are 10H-indolo[1,2-a]indole compounds that are formed by an intramolecular Aldol-type process. The indicators can be used in a wide array of applications relating, for example, to biological systems or optical data storage.

摘要翻译： 一种新颖的指示剂平台包含能够响应外部刺激转化成信号载体化合物的多个1H-吲哚-3-基指示剂化合物。 在一类指示剂化合物中，所得到的信号聚合物是通过分子间Aldol型方法形成的2-亚苄基二氢吲哚化合物; 在另一类指示剂化合物中，所得到的信号聚合物是通过分子内Aldol型方法形成的10H-吲哚并[1,2-a]吲哚化合物。 这些指标可用于涉及例如生物系统或光学数据存储的广泛应用。

公开(公告)号：US06558917B2

公开(公告)日：2003-05-06

申请号：US10147323

申请日：2002-05-17

申请人： Günter Schabert

发明人： Günter Schabert

IPC分类号： C12Q104

CPC分类号： C07F9/65522 ,  C12Q1/04 ,  C12Q1/045 ,  C12Q1/34 ,  C12Q1/44 ,  C12Q2334/22 ,  C12Q2334/52 ,  G01N33/533 ,  G01N2333/195 ,  G01N2333/916 ,  Y10S435/968

摘要： Compounds of formula (I) in which R1, R2, R3, R4 and R5 are hydrogen atoms or chromogenic substituents and X is hydroxyl, OR6 wherein R6 is selected from the group consisting of C1-C4 alkyl, or O−Me+ wherein Me+ is a cation derived from an organic or inorganic base; these compounds do not exhibit significant fluorescence but are capable of being cleaved by phosphatidyl-inositol-specific phospholipase C, an enzyme which is indicative of bacterial activity; the umbelliferyl moity resulting from such cleavage is a strong fluorogen thus providing effective test methods for various pathogenic bacteria, such as Listeria, Staphylococcus and Clostridium species. Also disclosed are plating media for detection of microorganisms that are capable of metabolic generation of a phosphatidyl inositol-specific phospholipase C (PI-PLC). The plating medium can be in a dry, liquid, or semi-liquid form, depending upon its water content, and comprise at least one compound capable of forming an aqueous gel when in contact with water; at least one nutrient capable of supporting growth of said microorganism; and at least one indicator compound of formula I and/or IV, notably 4-methylumbelliferyl myo-inositol-1-phosphate or salts thereof and 5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate or salts thereof. PI-PLC generated by the microorganisms of interest leads to cleavage of the indicator compounds causing formation of fluorescence and/or color suitable for identification of type and count of such hygienically and pathologically important microorganisms as Listeria species.

摘要翻译： 其中R 1，R 2，R 3，R 4和R 5是氢原子或显色取代基并且X是羟基的式（I）化合物，其中R 6选自C 1 -C 4烷基或O-Me +，其中Me +是 衍生自有机或无机碱的阳离子; 这些化合物不表现出显着的荧光，但能够被磷脂酰肌醇特异性磷脂酶C（一种指示细菌活性的酶）裂解; 由这种切割产生的伞形花序是强氟，从而为各种病原菌如李斯特菌，葡萄球菌和梭菌属提供有效的测试方法。 还公开了用于检测能够代谢产生磷脂酰肌醇特异性磷脂酶C（PI-PLC）的微生物的电镀培养基。 取决于其含水量，电镀介质可以是干燥，液体或半液体形式，并且包含至少一种当与水接触时能够形成水凝胶的化合物; 至少一种能够支持所述微生物生长的营养物质; 和至少一种式I和/或IV的指示剂化合物，特别是4-甲基伞形酮肌醇-1-磷酸或其盐和5-溴-4-氯-3-吲哚氧基肌醇-1-磷酸酯或其盐 。 由感兴趣的微生物产生的PI-PLC导致指示剂化合物的裂解，导致形成适合于鉴定如利斯特氏菌属的这种卫生和病理重要的微生物的类型和数量的荧光和/或颜色。

公开(公告)号：US06416970B1

公开(公告)日：2002-07-09

申请号：US09646528

申请日：2000-09-19

申请人： Günter Schabert ,  Lawrence Restaino

发明人： Günter Schabert ,  Lawrence Restaino

IPC分类号： C12Q104

CPC分类号： C12Q1/44 ,  C07F9/65522 ,  C12Q1/04 ,  C12Q1/34 ,  C12Q2334/22 ,  C12Q2334/52 ,  G01N2333/195 ,  G01N2333/916 ,  Y10S435/968 ,  Y10S435/975

摘要： The invention provides compounds of formula (I) in which R1, R2, R3, R4 and R5 are independently selected from hydrogen and chromogenic substituents, and X is selected from the group consisting of hydroxyl; OR6 wherein R6 is selected from the group consisting of C1-C4 alkyl; and O−Me+ wherein Me+ is a cation derived from an organic or inorganic base. A preferred species of formula (I) is 4-Methylumbelliferyl myo-inositol-1-phosphate and salts thereof with an organic or inorganic base. The invention also provides fluorogenic methods for detecting various pathogenic bacteria, e.g., Listeria, Staphylococcus and Clostridium species, using substrates containing at least one formula (I) compound. A kit for detecting a phosphatidyl-inositol-specific phospholipase C enzyme as an indication of bacterial activity is disclosed.

摘要翻译： 本发明提供式（I）化合物，其中R 1，R 2，R 3，R 4和R 5独立地选自氢和显色取代基，X选自羟基; OR 6，其中R 6选自C 1 -C 4烷基; 和O-Me +，其中Me +是衍生自有机或无机碱的阳离子。 式（I）的优选种类是4-甲基伞形酮肌醇-1-磷酸及其盐与有机或无机碱。 本发明还提供了使用含有至少一种式（I）化合物的底物检测各种致病细菌例如利斯特氏菌属，葡萄球菌属和梭菌属物种的荧光法。 公开了用于检测磷脂酰肌醇特异性磷脂酶C酶作为细菌活性指示的试剂盒。

公开(公告)号：US08940909B2

公开(公告)日：2015-01-27

申请号：US13266707

申请日：2010-05-06

申请人： Urs Spitz ,  Lukas Wick ,  Alexander Bayer ,  Christophe Weymuth ,  Günter Schabert

发明人： Urs Spitz ,  Lukas Wick ,  Alexander Bayer ,  Christophe Weymuth ,  Günter Schabert

IPC分类号： C07D209/70 ,  C07D209/36 ,  C07D487/04

CPC分类号： C07D209/36 ,  C07D209/70 ,  C07D487/04

摘要： A novel indicator platform comprises a plurality of 1H-lndol-3-yl indicator compounds that are capable of converting to a signalophore compound in response to an external stimulus. In one class of indicator compounds, the resulting signalophores are 2-benzylideneindoline compounds that are formed by an intermolecular Aldol-type process; in a further class of indicator compounds, the resulting signalophores are 10H-indolo[1,2-a]indole compounds that are formed by an intramolecular Aldol-type process. The indicators can be used in a wide array of applications relating, for example, to biological systems or optical data storage.

摘要翻译： 一种新颖的指示剂平台包含能够响应外部刺激转化成信号载体化合物的多个1H-吲哚-3-基指示剂化合物。 在一类指示剂化合物中，所得到的信号聚合物是通过分子间Aldol型方法形成的2-亚苄基二氢吲哚化合物; 在另一类指示剂化合物中，所得到的信号聚合物是通过分子内Aldol型方法形成的10H-吲哚并[1,2-a]吲哚化合物。 这些指标可用于涉及例如生物系统或光学数据存储的广泛应用。

公开(公告)号：US20140377783A1

公开(公告)日：2014-12-25

申请号：US13883067

申请日：2011-11-04

申请人： Lukas Wick ,  Urs Spitz ,  Christophe Weymuth ,  Günter Schabert ,  Thomas Mayer ,  Alexander Bayer

发明人： Lukas Wick ,  Urs Spitz ,  Christophe Weymuth ,  Günter Schabert ,  Thomas Mayer ,  Alexander Bayer

IPC分类号： G01N33/58 ,  C12Q1/04 ,  C12Q1/34 ,  C12Q1/10 ,  C09B57/00 ,  C12Q1/44

CPC分类号： G01N33/583 ,  C09B57/00 ,  C09B67/0083 ,  C12Q1/04 ,  C12Q1/10 ,  C12Q1/34 ,  C12Q1/44 ,  G01N2333/938

摘要： A novel type of dye systems comprises a selection of 10H-indolo[1,2-a]indole compounds (henceforth abbreviated as IO compounds) and (5H,7H)-indolo[1,2-a]quinoline compounds (henceforth abbreviated as IQ compounds) showing a solvatochromic effect and exhibiting strong fluorescence in a variety of materials such as polypropylene, polyethylene, oils, various solvents, emulsions. Also disclosed are various methods how the IO/IQ compounds can be administered, especially how they can be produced and administered in situ from a precursor, responding to external stimuli such as enzyme activity, temperature and so forth. The response of a precursor to external stimuli can also be used to determine the presence or absence of such stimuli.

摘要翻译： 一种新型染料体系包括10H-吲哚并[1,2-a]吲哚化合物（以下简称为IO化合物）和（5H，7H） - 吲哚并[1,2-a]喹啉化合物（以下简称为 IQ化合物），显示出溶剂化色素效应，并在各种材料如聚丙烯，聚乙烯，油，各种溶剂，乳液中表现出强烈的荧光。 还公开了如何施用IO / IQ化合物的各种方法，特别是如何从前体产生和原位施用，对外部刺激如酶活性，温度等进行响应。 前体对外部刺激的反应也可以用于确定这种刺激的存在或不存在。

公开(公告)号：US06660494B2

公开(公告)日：2003-12-09

申请号：US10021271

申请日：2001-12-19

申请人： Günter Schabert ,  Lawrence Restaino ,  Elon W. Frampton

发明人： Günter Schabert ,  Lawrence Restaino ,  Elon W. Frampton

IPC分类号： C12Q104

CPC分类号： C07F9/5728 ,  C12Q1/04 ,  C12Q1/44 ,  G01N2333/916 ,  Y10S435/975

摘要： Chromogenic 3-Indoxyl choline phosphate compounds of formula (I): wherein R is selected from the group consisting of hydrogen and C1-4 alkyl, such as methyl, ethyl, propyl and butyl while R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, halogen, cyano, nitro, carboxy, amino, amino substituted with one or two C1-4 alkyl groups, aminomethyl, hydroxy, C1-4 alkoxy, carboxyalkyl, and sulphonyl. These compounds are capable of being cleaved by lecithinase C leading to products which are calorimetrically detectable. The invention provides safe and sensitive detection of potentially pathogenic bacterial activity of such microbes as Clostridium perfringens, Bacillus cereus, Bacillus anthracis, Pseudomonas aeruginosa, Listeria monocytogenes, Heliobacter pylori, Legionella pneumophila, and others in material which may contain such activity typically including physiological samples, goods for consumption, such as food and beverages, and any other potentially infected objects or articles.

摘要翻译： 式（I）的显色3-吲哚基胆碱磷酸酯化合物：其中R选自氢和C 1-4烷基，例如甲基，乙基，丙基和丁基，而R 1，R 2，R R 3独立地选自氢，卤素，氰基，硝基，羧基，氨基，被一个或两个C 1-4烷基取代的氨基，氨基甲基，羟基，C 1-4烷氧基， 羧基烷基和磺酰基。 这些化合物能够被卵磷脂酶C裂解，导致可量热检测的产物。 本发明提供了安全和敏感的检测，例如产气荚膜梭菌，蜡状芽孢杆菌，炭疽芽孢杆菌，铜绿假单胞菌，单核细胞增生利斯特氏菌，幽门螺杆菌，嗜肺军团菌等可能具有这种活性的细菌活性，其中可能含有通常包括生理样品 消费品，如食品和饮料，以及任何其他可能感染的物体或物品。