公开(公告)号：US06514717B2

公开(公告)日：2003-02-04

申请号：US09960932

申请日：2001-09-25

申请人： Irena Y. Bronstein

发明人： Irena Y. Bronstein

IPC分类号： G01N3353

CPC分类号： C07H15/203 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/533 ,  G01N33/535 ,  G01N33/581 ,  G01N33/582 ,  G01N33/76

摘要： A kit for detecting a first substance in a sample including a stabilized 1,2-dioxetane bearing an enzyme-labile substituent, which is destabilized and caused to decompose by contacting the 1,2-dioxetane with an enzyme under conditions which cause the enzyme to cleave the enzyme-labile substituent from the dioxetane, thereby yielding a negatively charged oxygen anion bonded to the 1,2-dioxetane, which causes the 1,2-dioxetane to decompose without input from an external excitation energy source, the decomposition being accompanied by chemiluminescence; and a second component selected from the group consisting of a specific affinity substance (e.g., an antigen, an antibody or a nucleic acid probe) and an enzyme which destabilizes said 1,2-dioxetane.

摘要翻译： 一种用于检测样品中的第一物质的试剂盒，其包含具有酶不稳定取代基的稳定化的1,2-二氧杂环丁烷，其不稳定并通过使1,2-二氧杂环丁烷与酶在使酶引起的条件下接触而分解 从二氧杂环丁烷切割酶不稳定取代基，从而产生与1,2-二氧杂环丁烷键合的带负电荷的氧阴离子，这导致1,2-二氧环乙烷在没有外部激发能源的输入的情况下分解，分解伴随着 化学发光; 和选自特异性亲和物质（例如抗原，抗体或核酸探针）的第二成分和使所述1,2-二氧环乙烷不稳定的酶。

公开(公告)号：US06417380B1

公开(公告)日：2002-07-09

申请号：US09631300

申请日：2000-08-02

申请人： Irena Y. Bronstein ,  Brooks Edwards

发明人： Irena Y. Bronstein ,  Brooks Edwards

IPC分类号： C07F708

CPC分类号： C07H15/203 ,  C07C41/01 ,  C07C67/29 ,  C07C2603/74 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/581 ,  G01N33/582 ,  C07C43/215 ,  C07C43/1788 ,  C07C69/157

摘要： Compounds having the formula: wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: with an R-ylating agent (e.g., R2 SO4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: are produced by reacting a compound having the formula: with wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula are produced by reacting a compound of the formula with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups. The aforementioned compounds and procedures are useful in the synthesis of enzyme-cleavable 1,2-dioxetane ring systems that can serve as members of a binding pair employed, for example, in chemiluminescent immunoassays, DNA probe assays, and direct assays for an enzyme.

摘要翻译： 具有下式的化合物：其中T是聚亚烷基（例如，金刚烷-2-亚基）; R是C 1-20烷基，芳烷基或环烷基; 并且Y是通过在极性非质子溶剂中在碱金属醇盐的存在下使具有下式的化合物与R-衍生剂（例如R 2 SO 4）反应制备的荧光发色团（例如，间亚苯基）。 此外，具有下式的化合物是通过使具有下式的化合物：其中X是电负离子基团（例如卤素阴离子如氯离子），在路易斯碱（例如三烷基胺）存在下反应， 溶于非质子有机溶剂（如苯或甲苯）中。 此外，具有下式的化合物是通过使四-O-氧化的O-六吡喃糖苷卤化物的化合物反应，然后水解掉保护性酰基而制备的。 上述化合物和方法可用于合成可切割的1,2-二氧杂环丁烷环系统，其可以用作结合对的成员，例如在化学发光免疫测定，DNA探针测定和酶的直接测定中使用。

公开(公告)号：USRE36536E

公开(公告)日：2000-01-25

申请号：US958342

申请日：1997-10-27

申请人： Irena Y. Bronstein

发明人： Irena Y. Bronstein

IPC分类号： C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/655 ,  C07F9/6574 ,  C07H15/203 ,  C07H15/26 ,  G01N21/76 ,  G01N33/533 ,  G01N33/535 ,  G01N33/58 ,  G01N33/76 ,  G01N33/53

CPC分类号： C07H15/203 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  G01N21/76 ,  G01N33/533 ,  G01N33/535 ,  G01N33/581 ,  G01N33/76

摘要： In an assay method in which a member of a specific binding pair is detected by means of an optically detectable reaction, the improvement wherein the optically detectable reaction includes the reaction, with an enzyme, of a dioxetane having the formula ##STR1## where T is a cycloalkyl or polycycloalkyl group bonded to the 4-membered ring portion of the dioxetane by a spiro linkage; Y is a fluorescent chromophore; X is hydrogen, alkyl, aryl, aralkyl, alkaryl, heteroalkyl, heteroaryl, cycloalkyl, cycloheteroalkyl, or enzyme-cleavable group; and Z is hydrogen or an enzyme-cleavable group, provided that at least one of X or Z must be an enzyme-cleavable group, so that the enzyme cleaves the enzyme-cleavable group from the dioxetane to form a negatively charged substituent bonded to the dioxetane, the negatively charged substituent causing the dioxetane to decompose to form a luminescent substance that includes group Y of said dioxetane.

摘要翻译： 在其中通过光学可检测反应检测特异性结合对的成员的测定方法中，其中光学可检测的反应包括与酶具有下式的二氧环乙烷的反应：其中T是环烷基或 通过螺键键合到二氧杂环丁烷的4元环部分的多环烷基; Y是荧光发色团; X是氢，烷基，芳基，芳烷基，烷芳基，杂烷基，杂芳基，环烷基，环杂烷基或酶切割基团; 并且Z是氢或可酶切合基团，条件是X或Z中的至少一个必须是酶切割基团，使得酶从二氧杂环丁烷切割酶切割基团以形成结合到 二氧杂环丁烷，带负电荷的取代基，导致二氧杂环丁烷分解形成包含所述二氧杂环丁烷的Y基团的发光物质。

公开(公告)号：US5994073A

公开(公告)日：1999-11-30

申请号：US850009

申请日：1997-05-01

申请人： Irena Y. Bronstein ,  Brooks Edwards ,  John C. Voyta

发明人： Irena Y. Bronstein ,  Brooks Edwards ,  John C. Voyta

IPC分类号： C07D321/00 ,  C12Q1/68

CPC分类号： C09K11/07 ,  C07F9/12 ,  C07F9/6551

摘要： Chemiluminescent bioassays for the presence or concentration of an analyte in a sample use 1,2-dioxetanes as substrates for the enzyme of an enzyme complex that bind to the analyte. The chemiluminescence obtained from the decomposition of the dioxetane triggered by the enzyme through the formation of the corresponding 1,2-dioxetane oxyanion of the enzyme complex is enhanced by the addition of TBQ as an enhancement agent. Other polymeric quaternary onium salts can be used as enhancement agents in conjunction with enhancement additives which improve the ability of the enhancement agent to form hydrophobic regions in the aqueous sample, in which regions the 1,2-dioxetane oxyanion and its chemiluminescent decomposition products can be sequestered. A kit for performing such assays is also provided.

摘要翻译： 用于样品中分析物的存在或浓度的化学发光生物测定使用1,2-二氧杂环丁烷作为与分析物结合的酶复合物的酶的底物。 通过添加TBQ作为增强剂，增强了通过酶复合物形成相应的1,2-二氧杂环丁烷氧阴离子而由酶引发的二氧杂环丁烷的分解获得的化学发光。 其他聚合季铵盐可用作增强剂与增强添加剂一起使用，增强添加剂改善增强剂在水样品中形成疏水区的能力，其中1,2-二氧环乙烷氧阴离子及其化学发光分解产物可以是 隔离 还提供了用于进行这种测定的试剂盒。

公开(公告)号：US5831102A

公开(公告)日：1998-11-03

申请号：US598353

申请日：1996-02-08

申请人： Irena Y. Bronstein ,  Brooks Edwards ,  Rouh-Rong Juo

发明人： Irena Y. Bronstein ,  Brooks Edwards ,  Rouh-Rong Juo

IPC分类号： C07D321/00 ,  C12Q1/68

CPC分类号： C07F9/12 ,  C07F9/6551 ,  C09K11/07 ,  Y10S435/81 ,  Y10S436/80 ,  Y10S436/808

摘要： Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; and R.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sup.1 and R.sub.2 represent individual substituents the R.sub.2 substituent is aromatic, heteroaromatic, or an unsaturated substituent in conjugation with an aromatic ring, and that at least one of R.sub.1 and R.sub.2 is, or R.sub.1 and R.sub.2 taken together are, an enzymatically cleavable labile group-substituted fluorescent chromophore group that produces a luminescent substance when the enzymatically cleavable labile substituent thereof is removed by an enzyme. The corresponding dioxetanes which, instead of being substituted at the 5' or 7', or at the 5' and 7' positions, instead contain a 4' methylene group, are also disclosed, as are intermediates for all these 3-substituted adamant-2'-ylidenedioxetanes, and their use as reporter molecules in assays.

公开(公告)号：US5756770A

公开(公告)日：1998-05-26

申请号：US630635

申请日：1990-12-20

申请人： Irena Y. Bronstein ,  Brooks Edwards

发明人： Irena Y. Bronstein ,  Brooks Edwards

IPC分类号： C07C43/196 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/655 ,  C07F9/6574 ,  C07H15/203 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/58 ,  C07F9/06

CPC分类号： C07H15/203 ,  C07C43/196 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/581 ,  G01N33/582 ,  C07C2103/00 ,  C07C2103/74

摘要： A novel synthesis of 1,2-dioxetane phosphate alkali metal salts and novel intermediates employed in this synthesis are disclosed. A hydroxyaryl enol ether alkali metal salt having the formula: ##STR1## wherein T can be an unsubstituted or substituted adamant-2'-ylidene group, R.sup.3 can be a methyl group, Y can be a phenyl group and M.sup.+ can be a sodium cation, is reacted with a phosphorohalidate to give the corresponding enol ether ethylene phosphate, which is then reacted with an alkali metal cyanide to give the corresponding enol ether cyanoethyl phosphate diester alkali metal salt intermediate. Singlet oxygen addition to this enol ether cyanoethyl phosphate diester alkali metal salt intermediate to give the corresponding 1,2-dioxetane cyanoethyl phosphate diester alkali metal salt, followed by .beta.-elimination of the cyanoethyl group using an alkali metal hydroxide or the like, gives the corresponding 1,2-dioxetane phosphate alkali metal salt.

摘要翻译： 公开了在该合成中使用的1,2-二氧杂环丁烷磷酸碱金属盐和新型中间体的新型合成。 具有下式的羟基芳基烯醇醚碱金属盐：其中T可以是未取代或取代的金刚烷-2'-亚基，R 3可以是甲基，Y可以是苯基，M +可以是钠阳离子 与卤代磷酸酯反应，得到相应的烯醇醚乙烯磷酸酯，然后与碱金属氰化物反应，得到相应的烯醇醚氰乙基磷酸二酯碱金属盐中间体。 将该烯醇醚氰乙基磷酸二酯碱金属盐中间体加入单线态氧，得到相应的1,2-二氧杂环丁烷氰乙基磷酸二酯碱金属盐，然后使用碱金属氢氧化物等与氰基乙基进行β-烯化反应，得到 相应的1,2-二氧杂环丁烷磷酸盐碱金属盐。

公开(公告)号：US5707559A

公开(公告)日：1998-01-13

申请号：US23649

申请日：1987-03-09

申请人： Arthur Paul Schaap ,  Irena Y. Bronstein

发明人： Arthur Paul Schaap ,  Irena Y. Bronstein

IPC分类号： G01N21/78 ,  C07C37/00 ,  C07C37/62 ,  C07C39/19 ,  C07C39/23 ,  C07C39/38 ,  C07C43/178 ,  C07C51/15 ,  C07C69/14 ,  C07C69/24 ,  C07C69/76 ,  C07C305/04 ,  C07D207/46 ,  C07D311/82 ,  C07D311/86 ,  C07D321/00 ,  C07D405/12 ,  C07D407/10 ,  C07D407/12 ,  C07D417/12 ,  C07D493/10 ,  C07D495/04 ,  C07F7/18 ,  C07F9/12 ,  C07F9/6541 ,  C07F9/655 ,  C07F9/6558 ,  C07F9/6561 ,  C07H15/203 ,  C09K11/07 ,  C09K3/00 ,  C07C49/213

CPC分类号： C07D405/12 ,  C07C37/00 ,  C07C37/055 ,  C07C37/62 ,  C07C51/15 ,  C07D207/46 ,  C07D311/82 ,  C07D321/00 ,  C07D407/10 ,  C07D407/12 ,  C07D417/12 ,  C07D493/10 ,  C07D495/04 ,  C07F7/1852 ,  C07F7/1856 ,  C07F9/6541 ,  C07F9/65512 ,  C07F9/65522 ,  C07F9/65586 ,  C07F9/6561 ,  C07H15/203 ,  C07C2103/18 ,  C07C2103/74

摘要： Novel light producing 1,2-dioxetanes are described of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.

摘要翻译： 描述了新的产生1,2-二氧杂环丁烷的通式为“IMAGE”的化合物，其中ArOX是被X氧基取代的芳环，A是被去除的有机基团，当通过除去X而触发时，可使1,2-二氧杂环丁烷产生光 X是化学上不稳定的基团，它被活化剂除去。 可以触发1,2-二氧环乙烷化合物在室温下产生光。

公开(公告)号：US5543295A

公开(公告)日：1996-08-06

申请号：US233085

申请日：1994-04-25

申请人： Irena Y. Bronstein ,  Brooks Edwards ,  Rouh-Rong Juo

发明人： Irena Y. Bronstein ,  Brooks Edwards ,  Rouh-Rong Juo

IPC分类号： C07C43/178 ,  C07C43/196 ,  C07C43/215 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/655 ,  C07F9/6574 ,  C07H15/203 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/58 ,  C12Q1/68

CPC分类号： C07H15/203 ,  C07C43/1788 ,  C07C43/196 ,  C07C43/215 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  C12Q1/34 ,  G01N33/581 ,  G01N33/582 ,  C07C2103/00 ,  C07C2103/74 ,  Y10S435/81 ,  Y10S435/968 ,  Y10S436/80 ,  Y10S436/808

摘要： Enzymatically clearable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically clearable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; and R.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sub.1 and R.sub.2 represent individual substituents the R.sub.2 substituent is aromatic, heteroaromatic, or an unsaturated substituent in conjugation with an aromatic ring, and that at least one of R.sub.1 and R.sub.2 is, or R.sub.1 and R.sub.2 taken together are, an enzymatically cleavable labile group-substituted fluorescent chromophore group that produces a luminenscent substance when the enzymatically cleavable labile substituent thereof is removed by an enzyme. The corresponding dioxetanes which, instead of being substituted at the 5' or 7', or at the 5' and 7' positions, instead contain a 40' mehtylene group, are also disclosed, as are intermediates for all these 3-substituted adamant-2'-ylidenedioxetanes, and their use as reporter molecules in assays.

摘要翻译： 公开了能够在分解时产生光能的化学发光化学发光的1,2-二氧杂环丁烷化合物，其在可消除其可酶切的不稳定取代基被有意地切割的键之前在室温下基本稳定。 这些化合物可以由下式表示：其中：X和X1各自独立地表示氢，羟基，卤素取代基，未取代的低级烷基，羟基（低级）烷基，卤代（低级） ）烷基，苯基，卤代苯基，烷氧基苯基，羟基烷氧基，氰基或酰胺基，其中X和X 1中的至少一个不是氢; 并且R 1和R 2各自或一起表示当二氧杂环丁烷化合物被酶切并且满足二恶丁环化合物的4-碳原子的化合价时不干扰光的产生的有机取代基，条件是如果R1和 R2代表单个取代基，R2取代基是芳族的，杂芳族的，或与芳环共轭的不饱和取代基，并且R1和R2中的至少一个是，或者R1和R2一起是可酶切的不稳定基取代的荧光 当其酶促切割的不稳定取代基被酶除去时产生光敏物质的发色团。 还公开了相应的二氧杂环丁烷，而不是在5'或7'或5'和7'位置被取代，而是含有40'甲基，也可以是所有这些3-取代的金刚烷基 - 2'-亚基二氧杂环丁烷，以及它们在测定中作为报道分子的用途。

公开(公告)号：US5330900A

公开(公告)日：1994-07-19

申请号：US806928

申请日：1991-12-12

申请人： Irena Y. Bronstein ,  Brooks Edwards ,  Rouh-Rong Juo

发明人： Irena Y. Bronstein ,  Brooks Edwards ,  Rouh-Rong Juo

IPC分类号： C07C43/178 ,  C07C43/196 ,  C07C43/215 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/655 ,  C07F9/6574 ,  C07H15/203 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/58 ,  C12Q1/68

CPC分类号： C07H15/203 ,  C07C43/1788 ,  C07C43/196 ,  C07C43/215 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  C12Q1/34 ,  G01N33/581 ,  G01N33/582 ,  C07C2103/00 ,  C07C2103/74 ,  Y10S435/81 ,  Y10S435/968 ,  Y10S436/80 ,  Y10S436/808

摘要： Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sub.1 and R.sub.2 represent individual substituents the R.sub.2 substituent is aromatic, heteroaromatic, or an unsaturated substituent in conjugation with an aromatic ring, and that at least one of R.sub.1 and R.sub.2 is, or R.sub.1 and R.sub.2 taken together are, an enzymatically cleavable labile group-substituted fluorescent chromophore group that produces a luminescent substance when the enzymatically cleavable labile substituent thereof is removed by an enzyme.The corresponding dioxetanes which, instead of being substituted at the 5' or 7', or at the 5' and 7' positions, instead contain a 4' methylene group, are also disclosed, as are intermediates for all these 3-substituted adamant-2'-ylidenedioxetanes, and their use as reporter molecules in assays.

摘要翻译： 公开了能够在分解时产生光能的酶促切割的化学发光的1,2-二氧杂环丁烷化合物，在其中有可能将可酶切割的不稳定取代基故意断裂的键之间在室温下基本稳定。 这些化合物可以由下式表示：其中：X和X1各自独立地表示氢，羟基，卤素取代基，未取代的低级烷基，羟基（低级）烷基，卤代（低级） ）烷基，苯基，卤代苯基，烷氧基苯基，羟基烷氧基，氰基或酰胺基，其中X和X 1中的至少一个不是氢; 并且R 1和R 2各自或一起表示当二氧杂环丁烷化合物被酶切并且满足二恶丁环化合物的4-碳原子的化合价时不干扰光的产生的有机取代基，条件是如果R1和 R2代表单个取代基，R2取代基是芳族的，杂芳族的，或与芳环共轭的不饱和取代基，并且R1和R2中的至少一个是，或者R1和R2一起是可酶切的不稳定基取代的荧光 当其酶促切割的不稳定取代基被酶除去时产生发光物质的发色团。 也公开了相对于在5'或7'或5'和7'位置取代含有4'亚甲基的二氧杂环丁烷，以及所有这些3-取代的金刚烷基 - 2'-亚基二氧杂环丁烷，以及它们在测定中作为报道分子的用途。

公开(公告)号：US5177241A

公开(公告)日：1993-01-05

申请号：US537788

申请日：1990-06-14

申请人： Irena Y. Bronstein ,  Brooks Edwards

发明人： Irena Y. Bronstein ,  Brooks Edwards

IPC分类号： C07C43/178 ,  C07C43/196 ,  C07C43/215 ,  C07C69/00 ,  C07D321/00 ,  C07F9/12 ,  C07F9/655 ,  C07F9/6574 ,  C07H15/203 ,  C07H15/26 ,  C12Q1/34 ,  E21B23/03 ,  E21B47/00 ,  E21B47/06 ,  G01N21/76 ,  G01N33/535 ,  G01N33/58 ,  G01N33/76

CPC分类号： C07H15/203 ,  C07C43/1788 ,  C07C43/196 ,  C07C43/215 ,  C07C69/157 ,  C07D321/00 ,  C07F9/12 ,  C07F9/65512 ,  C07F9/65742 ,  C07H15/26 ,  C12Q1/34 ,  G01N21/76 ,  G01N33/535 ,  G01N33/581 ,  G01N33/582 ,  G01N33/76 ,  C07C2103/74

摘要： Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula ##STR5## are produced by reacting a compound of the formula ##STR6## with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups. The aforementioned compounds and procedures are useful in the synthesis of enzyme-cleavable 1,2-dioxetane ring systems that can serve as members of a binding pair employed, for example, in chemiluminescent immunoassays, DNA probe assays, and direct assays for an enzyme.

摘要翻译： 具有下式的化合物：其中T是多环亚烷基（例如，金刚烷-2-亚基）; R是C 1-20烷基，芳烷基或环烷基; Y是荧光发色团（例如，间亚苯基），它是通过在碱金属醇盐存在下在极性非质子中反应制备的具有下式的化合物：＆lt; IMAGE＆gt;和R-衍生剂（例如R 2 SO 4） 溶剂。 此外，具有下式的化合物：是通过使下式化合物与其中X是电负离子基团（例如卤素阴离子如氯离子）反应的化合物与 溶解在非质子有机溶剂（例如苯或甲苯）中的路易斯碱（例如三烷基胺）。 此外，具有式“IMAGE”的化合物通过使式“IMAGE”的化合物与四-O-酰化的O-六吡喃苷卤化物反应，然后水解掉保护性酰基而产生。 上述化合物和方法可用于合成可切割的1,2-二氧杂环丁烷环系统，其可以用作结合对的成员，例如在化学发光免疫测定，DNA探针测定和酶的直接测定中使用。