KR900001820A - 1, 2-디옥세탄에서 증대된 화학루미센스를 제공하는 방법과 조성물 - Google Patents

1, 2-디옥세탄에서 증대된 화학루미센스를 제공하는 방법과 조성물

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KR900001820A
KR900001820A KR1019890010603A KR890010603A KR900001820A KR 900001820 A KR900001820 A KR 900001820A KR 1019890010603 A KR1019890010603 A KR 1019890010603A KR 890010603 A KR890010603 A KR 890010603A KR 900001820 A KR900001820 A KR 900001820A
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dioxetane
compound
activator
aryl
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KR930008603B1 (ko
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파울 샤아프 아더
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더 보드 오브 가버너 오브 웨인 스테이트 유니버시티
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Abstract

내용 없음

Description

1,2-디옥세탄에서 증대된 화학루미센스를 제공하는 방법과 조성물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 크실렌에서의 인산염-치환된 디옥세탄 2c의 열분해에 대한 아레니우스 도면을 나타낸다.
제2도는 브롬화 세틸트리메틸암모늄(CTAB)의 농도의 함수로서 디오옥세탄 2b의 염기-개시되는 반응에 대한 화학투미네센스 양의 수율의 도면을 나타낸다.
제2a도는 형광보조-계면활성제와 CTAB 계면활성제가 있는 디옥세탄의 이상적인 구조를 나타낸다.
제3도는 37℃에서 2-아미노-2-메틸-1-프로판올(221)완충액(pH10.3)에든 알칼리 포스파타제를 포함하는 100㎕의 사람 혈액혈정을 가진 10-5M 디옥세탄에 대한 시간에 대한 화학투미네센스 강도의 도면을 나타낸다.

Claims (41)

  1. (a) 다음 일반식의 안정된 1,2-디옥세탄(dioxetane)과 가깝게 위치한 관계에 있는 (in a closely spaced relationship) 형광화합물을 제공하고
    이식에서 ArOX는 활성제에 의해서 X를 제거하기 위하여 개시되었을 때 불안정한 산화를 중간물질인 1,2-디옥세탄 화합물이 분해하여 전자에너지를 방출하여 빛을 형성시키고 그리고 다음 일반식의 두개의 카르보닐 함유화합물을 형성하는 X-옥시 그룹으로 치환된 아틸그룹을 나타내고
    이식에서 X는 활성제에 의해서 제거되어 불안정된 산화물 중간물질인 1,2-디옥세탄을 형성하는 화학적으로 불한정한 그룹이고 그리고 이식에서 A는 빛의 발생을 허용하는 부동태 유기그룹이고 ; 그리고 (b) 활성제는 안정된 1,2-디옥세탄을 분해하며 이경우 형광화합물은 불안정한 산화물 중간물질의 분해시에 발생된 전자에너지를 수용하여 디옥세탄만의 단독의 개시에 의해서 발생되는 것보다 더욱 강한 빛을 발생시키는 것을 포함하는 광발생 방법.
  2. (a) 다음 일반식의 안정된 1,2-디옥세탄과 가깝게 위치한 관계에 있는 형광화합물을 제공하고
    이식에서 R1과 R2는 함께 그리고 R3와 R4는 함께 탄소 이외에도 원자(N,S,O 또는 P)및 아릴고리를 포함할 수 있는 스피로 융합된 알킬렌 그룹으로서 결합될 수 있으며 상기식에서 R1과 R2또는 R3과 R4중 최소한 하나가 산, 염기, 염, 효소, 무기 및 유기촉매 그리고 전자공여체에서 선택된 활성화제로서 X의 제거를 개시했을 때 불안정한 산화물 중간물질 1,2-디옥세탄 화합물을 형성하여서 불안정한 1,2-디옥세탄 화합물이 분해하여서 전자에너지를 방출하여 광을 형성하고 그리고 다음 일반식의 두가지의 카르보닐 함유 화합물을 형성하는 X-옥시 그룹으로 치환된 아릴고리를 가지는 아필그불이고 :
    이식에서 X-옥시 그룹에 의해서 치환되지 않는 R1, R2, R3 또는 R4는 탄소 그리고 안정된 1,2-디옥세탄 화합물에 대해서 안정도를 제공하는 유기그룹을 포함하는 헤테로 원자이며, 그리고 상기식에서 X는 불안정한 산화물 중간물질을 형성하기 위하여 활성화제에 의하여 제거되는 화학적으로 불한정한 그룹으로 ; 그리고 (b) 활성제에 의하여 안정된 1,2-디옥세탄을 분해하고, 이경우 형광화합물이 불안정한 산화를 중간물질의 분해시에 발생된 전자 에너지를 수용하여 디옥세탄 하나만의 개시에 의해서 발생된 것 보다 더욱 강한 빛을 만드는 것을 포함하는 광발생 방법
  3. (a) 다음 일반식 안정된 디옥세탄 화합물과 가깝게 위한 관계에 있는 형광 화합물을 제공하고 :
    이식에서 R1은 알킬, 알콕시, 알라옥시 디알킬아미노, 트리알킬 또는 아릴실록시 및 R2에 의해서 스피로 융합된 아릴그룹을 포함하는 아릴그룹에서 선택하고 상기식에서 R2는 산, 염기, 염, 효소, 무기 및 유기촉매 그리고 전자공여체에서 선택된 활성화제에 의하여 X를 제거하도록 개시되었을 때 불안정된 산화물 중간물질인 1,2-디옥세탄 화합물을형성하여서 불한정한 1,2-디오세탄 화합물이 분해하여 전자에너지를 방출하여 빛을 형성케 하고 그리고 다음 일반식의 두개의 카르보닐 함유 화합물을 형성하는 X-옥시그룹으로 치환되고 R1을 포함할 수 있는 아릴그룹이고 :
    이식에서 X는 활성화제에 의해서 제거되어 불안정한 산화물중간물질을 형성하는 화학적으로 불안정한 그룹이고 그리고 R3및 R4는 아릴, 헤테로알킬 및 스피로 융합된 다환식 알킬 및 다환식 아릴그룹과 함께 결합할 수 있는 알킬 그룹에서 선택되고 ; 그리고 (b) 활성화제에 의해서 안정된 1,2-디옥세탄을 분해하고 이경우 형광 화합물은 불안정한 산화물 중간물질의 분해시에 발생한 전자에너지를 수용하여 디옥세탄 하나만의 개시에 의해서 발생된 것보다 훨씬 강한 빛을 만드는 것을 포함하는 광발생 방법.
  4. 제1항에 있어서, 1,2-디오세탄 화합물을 X를 제거시키는 활성화제로서 생물학적 공급원에서 얻은 효소에 의해서 분해시키는 방법.
  5. 제4항에 있어서,1,2-디옥세탄이 X-옥시그룹으로서 인산염 그룹을 가지고 효소는 알칼리인산 효소인 방법.
  6. 제4항에 있어서,1,2-디옥세탄이 OX그룹으로서 아세톡시 그룹을 가지고 효소가 아세틸콜린스테라제인 방법.
  7. 제4항에 있어서,1,2-디옥세탄이 OX그룹으로서 아세톡시 그룹을 가지고 효소가 아릴에스테라제인 방법.
  8. 제1항에 있어서, 이 방법을 면역검사법 도는 핵산 탐침의 일부로서 실시하는 방법.
  9. 제2항에 있어서, R3및 R4를함께 결합하여 6내지 30개의 탄소원자 또는 헤테로 원자(N,S,O 또는 P)를 포함하는 다환식 폴리알킬렌 그룹을 형성하는 방법.
  10. 제9항에 있어서, R2를 X-옥시그룹을 포함하는 나프릴 및 페닐그룹에서 선택하고 R1이 메톡시그룹인 방법.
  11. 제10항에 있어서, X-옥시그룹을 히드록시, 트리알킬 또는 아릴실릴옥시, 무기 옥시산염,산소-피라노시드, 아릴카르보닐에스테르 및 알킬카르복시 에스테르에서 선택하고 그리고 X를 활성제로 제거하는 방법.
  12. 제11항에 있어서, X-옥시그룹이 인산염 그룹이고 그리고 인산염그룹을 활성화제로서 인산효소로서 제거하는 방법.
  13. 제11항에 있어서, X-옥시그룹을 알킬 및 아릴카르복시 에스테르 그룹에서 선택하고 그리고 카르복시그룹을 에스테라제를 제거하는 방법.
  14. 제2항에 있어서,1,2-디옥세탄 화합물을 X를 제거하는 활성화제로서 생물학적 공급원으로부터의 효소에 의해서 분해시키는 방법.
  15. 제14항에 있어서, 1,2-디옥세탄이 X-옥시그룹으로 인산염 그룹을 가지고 효소가 알칼리 인산효소인 방법.
  16. 제14항에 있어서, 1,2-디옥세탄이 X-옥시그룹으로서 아세톡시그룹을 가지고 효소가 세틸콜린에스테라제인 방법.
  17. 제13항에 있어서, 1,2-디옥세탄이 X-옥시그룹으로서 아세톡시그룹을 가지고 효소가 아릴에스테라제인 방법.
  18. 제2항에 있어서, 이방법을 면역검사법이나 또는 핵산 탐침의 일부로서 실시하는 방법.
  19. 제2항에 있어서, R1이 알톡시그룹인 방법.
  20. 제2항에 있어서, R1이 메톡시그룹이고, R2가 X-옥시그룹으로 치환된 체닐그룹이고 그리고 R3과 R4가 아다만틸 그룹으로서 함께 결합된 방법.
  21. 제1항에 있어서, X-옥시그룹을 하드록시, 아세톡시, 인산염 및 산소 피라노시드에서 선택하는 방법.
  22. 제1항에 있어서, 형광화하물을 1,-디옥세탄과의 혼합물에 제공하는 방법.
  23. 제1항에 있어서, 양이온 계면활성제와 형광화합물을 1,2-디옥세탄과의 혼합물에 제공하는 방법.
  24. 제23항에 있어서, 계면활성제가 세틸트리메틸 암모늄염인 방법.
  25. 제24항에 있어서, 형광화합물이 푸루어레신(fluorescein)화합물인 방법.
  26. 제1항에 있어서, 형광화합물이 계면활성제로서 세틸트리메틸 암모늄염과 미포(mycelles)로서 작용하는 계면활성제로서 또한 작용하는 5-(N-테트라데카-노닐아미노-풀루오네신)인 방법.
  27. 제1항에 있어서, 형광화합물이 계면활성제로서 작용하는 세틸트리에틸암모늄염을 가진 보조-계면활성제로서 또는 작용하는 1-헥사데실-6-히드록시-2-벤조트리아조이미드인 방법.
  28. 제1항에 있어서, 디옥세틴과 형광화합물이 미포, 리포즘, 역미포, 미세유탁액, 필름, 단일층 또는 중합체와 가깝게 위치한 관계인 방법.
  29. (a) 형광 화합물 ; 그리고 (b) 다음 일반식의 안정된 1,2-디옥세탄을 포함하며 개시 시에 빛을 발생시키는 조성물 :
    이식에서 ArOX는 X를 제거하기 위하여 개시되었을 때 불안정한 산화물 중간물질 1,2-디옥세탄을 형성하여 이 불안정한 1,2-디옥세탄 화합물이 분해하여 전자에너지를 방출하여 빛을 형성하고 그리고 다음 일바식의 두개의 카르보닐 함유 화합물을 형성하는 X-옥시 그룹으로 치환된 아릴그룹을 나타내고 :
    이경우 X는 활성화제에 의하여 제거되어 불안정한 산화물 중간물질 1,2-디옥세탄을 형성하는 화학적으로 불안정한 그룹이고 상기식에서 A는 빛을 발생시키는 부동태의 유기 그룹이고 이경우 안정된 1,2-디옥세탄은 활성화제에 의하여 분해되고 형광물질은 불안정한 산화물 중간물질의 분해시에 발생된 전자에너지를 수용하여 디옥세탄 단독으로 개시되어 만드는 것보다 더욱 강한 빛을 발생시킨다.
  30. (a) 형광 화합물을 제공하고 ; 그리고 (b) 다음 일반식의 안정된 1,2-안정된 1,2디옥세탄 화합물을 포함하며 개시시에 빛을 발생시키는 조성물 :
    이식에서 R1과 R2 그리고 R3와 R4는 함께 탄소 이외에도 헤테로원자(N,S,O 또는 P)와 아릴고리를 포함할 수 있는 스피로 융합된 알킬렌 그룹으로서 결합할 수 있고 이경우 R1과 R2그리고 R3과 R4중의 최소한 X를 제거하기 위하여 하나가 산, 염기, 염, 효소, 무기 및 유기촉매 및 전자공여체에서 선택된 활성화제에 의하여 개시되었을 때 불안정한 산화물 중간물질 1,2-디옥세탄을 형성하여서 불안정한 1,2-디옥세탄 을 분해하고 전자에너지를 방출하여 빛을 발생시키고 다음 일반식의 두개의 카르보닐 함유 화합물을 형성하는 X-옥시그룹으로 치환된 아릴그룹이고 :
    이식에서 R1, R2, R3 또는 R4는 안정도된 1,2-디옥세탄 화합물에 대해서 안정도를 제공하는 유기그룹을 포함하고 그리고 X-옥시 그룹에 의해서 치환되지 안흥며 그리고 위의 경우에서 X는 활성화제에 의해서 제거되어 불한정한 산화물 중간 물질을 형성하는 화학적으로 불안저한 그룹이고 이때 안정된 1,2-디옥세탄을 활성제에 의해서 분해되어 형광화합물이 불안정한 산화를 중간물질의 분해시에 발생한 전자에너지를 수용하여 디옥세탄 단독으로 개시되어 발생된 것 보다 훨씬 강한 빛을 발생시킨다.
  31. (a) 형광 화합물을 제공하고 ; 그리고 (b) 다음 일반식의 안정된 디옥세탄 화합물을 포함하며 광을 발생시키는 조성물 :
    이식에서 R1은 알킬, 알콕시, 알라옥시 디알킬아미노, 트리알킬 또는 아릴실록시 그리고 R2로 스피로 융합된 아릴그룹을 포함하는 아릴그룹에서 선택하고 이식에서 R2는 X를 제거하기위하여 산, 염기, 염, 효소, 무기 및 유기촉매 그리고 전자공여체에서 선택된 활성화제에 의하여 개시되었을 때 불안정한 산화물 중간물질인 1,2-디옥세탄을 형성하여서 불한정한 1,2-디옥세탄 화합물을 분해시키고 전자에너지로 방출시켜 빛을 발생키기고 그리고 다음 일반식의 두개의 카르보닐 함유 화합물을 형성하는 X-옥시그룹으로 치환되고 R1을 포함할 수 있는 아릴그룹이고 :
    이경우 X는 활성화제에 의해서 제거되어 불안정한 산화물 중간물질을 형성하는 화학적으로 불안정된 그룹이고 그리고 R3및 R4는 스피로 융합된 다환식 알킬 및 다환식 아릴그룹과 함께 결합할 수 있는 아릴, 헤테로 알킬 및 알킬그룹에서 선택되고 이경우 안정된 1,2-디옥세탄은 활성화제에 의하여 분해하고 그리고 이경우 형광화합물은 불안정한 산화물 중간물질의 분해시 발생한 전자에너지를 수용하여 디옥세탄 단독으로 개시되어 발생된 것보다 훨씬 강한 빛을 발생시킨다.
  32. 제29항에 있어서, 디옥세탄 내 형광화합물의 몰비가 약 1000대 내지 1대 1의 범위인 조성물,
  33. 제29항에 있어서, 형광 화합물의 를루오레센 화합물인 조성물.
  34. 제29항에 있어서, 양이온성 계면활성아제를 이 조성물에 제공하는 조성물.
  35. 제30항에 있어서, R1이 메톡시 그룹이고, R2는 X-옥시그룹으로 치환된 페닐그룹이고 그리고 R3나 R4는 아다만틸그룹으로서 함께 결합된 조성물.
  36. 제35항에 있어서, X-옥시그룹은 히드록시, 트리알킬 또는 아릴실릴옥시, 무기옥시산염, 산소-피라노시드, 아릴카르보닐 에스테르 및 알킬카르복시 에스테르에서 선택되고 그리고 X는 활성화제에 의하여 제거되는 조성물.
  37. 제36항에 있어서, 형광화합물이 풀루오레신 화합물인 조성물.
  38. 제37항에 있어서, 양이온성 계면활성제를 이 조성물에 제공하고 형광화합물을 보조-계면 활성제를 제공하는 탄화수소 사슬과 결합되고 그리고 디록세탄은 약 10-1내지 10-6M 범위의 양으로 존재하고 계면활성제는 10-4M이상의 양으로 존재하고 그리고 보조-계면활성제는 10-3내지 10-6M의 범위의 양으로 존재하는 조성물.
  39. 제38항에 있어서, 계면활성제가 세틸트리메틸 암모늄염인 조성물.
  40. 제29항에 있어서, 디옥세틴과 형광화합물이 미포, 리포좀, 역미포, 미세유탁엑, 필름, 단일층 또는 중합체와 가깝게 위치한 관계에 있는 조성물.
  41. 제31항에 있어서, 디옥세틴과 형광화합물이 미포, 리포좀, 역미포, 미세-유탁액, 필름, 단일층 또는 중합체와 가깝게 위치한 관계에 있는 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890010603A 1988-07-27 1989-07-27 1, 2-디옥세탄에서 증대된 화학루미센스를 제공하는 방법과 조성물 KR930008603B1 (ko)

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US07/224,681 US5004565A (en) 1986-07-17 1988-07-27 Method and compositions providing enhanced chemiluminescence from 1,2-dioxetanes

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DE68909345T3 (de) 1998-12-10
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ATE94895T1 (de) 1993-10-15
ES2037638T1 (es) 1993-07-01
JPH07121237B2 (ja) 1995-12-25
KR930008603B1 (ko) 1993-09-10
EP0510721A3 (en) 1993-03-03
JPH0670797A (ja) 1994-03-15
US6133459A (en) 2000-10-17
DE510721T1 (de) 1993-04-08
EP0352713A1 (en) 1990-01-31
US5004565A (en) 1991-04-02
AU603736B2 (en) 1990-11-22
CN1040980A (zh) 1990-04-04
DE352713T1 (de) 1990-07-26
GR930300010T1 (ko) 1993-04-28
ES2013226T3 (es) 1994-11-16
CA1340574C (en) 1999-06-01
EP0352713B1 (en) 1993-09-22
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US5891626A (en) 1999-04-06
EP0518387A2 (en) 1992-12-16
GR900300085T1 (en) 1991-07-31
EP0510721A2 (en) 1992-10-28
DE68909345D1 (de) 1993-10-28
JPH0791536B2 (ja) 1995-10-04
ES2013226A4 (es) 1990-05-01
US6107024A (en) 2000-08-22
DE68909345T2 (de) 1994-01-13
AU3664589A (en) 1990-02-01
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