KR950702546A - 개선된 화학 발광성 1,2-디옥세탄(Improved chemiluminescent 1, 2-dioxetanes) - Google Patents

개선된 화학 발광성 1,2-디옥세탄(Improved chemiluminescent 1, 2-dioxetanes) Download PDF

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KR950702546A
KR950702546A KR1019950700026A KR19950700026A KR950702546A KR 950702546 A KR950702546 A KR 950702546A KR 1019950700026 A KR1019950700026 A KR 1019950700026A KR 19950700026 A KR19950700026 A KR 19950700026A KR 950702546 A KR950702546 A KR 950702546A
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dioxetane
enzyme
chlorine
kit
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KR1019950700026A
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KR0154209B1 (en
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브로스테인 아이레나
에드워즈 브룩스
스팍스 앨리슨
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아이레나 브론스테인
트로픽스, 인코퍼레이티드(Tropix, Inc.)
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Priority claimed from US08/057,903 external-priority patent/US5538847A/en
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Abstract

시그날 세기, S/N비율, T1/2등과 같은 개선된 화학 발광성을 갖는 신고한 1, 2-디옥세탄은 환의 잔여 탄소 원자는 알콕시, 아릴옥시 또는 아릴알콕시 치환체 및 페닐 또는 나프틸 환을 가지며, 이 방향족 환은 페닐 그룹상에 메타 위치에, 또는 나프틸 환상에서 비공액 위치에 OX 부위(여기에서 X는 효소-불안정성 그룹이며, OX부위는 디옥세탄에서 유리될 때 분해되어 화학 발광하는 옥시 음이온을 형성한)를 가지며, 아릴 환이 전자-활성 치환제 Z를 추가로 갖는 스피로아다만틸 1, 2-디옥세탄에 의해 제공된다. 디옥세탄 환에 대한 결합 이치에 인접하지 않은 위치에 있는 Z치환체의 성질 및 위치는 디옥세탄의 성질에 강력하게 영향을 미친다. 분석법 및 이러한 분석법의 수행을 위한 키트는 디옥세탄, X 그룹을 분해시킬 수 있는 효소, 및 특정의 경우에 멤브레인 및 화학 발광성 증진제를 포함한다.

Description

개선된 화학 발광성 1,2-디옥세탄(Improved chemiluminescent 1, 2-dioxetanes)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도 및 2도는 페닐 부위가 4위치에 염소 치환체를 갖는 본 발명의 화합물 이나트륨-2-클로로-5-(4-메톡시스피로[1,2-디옥세탄-3,2'-(5-클로로)-트리사이클로-[3.3.3.33,7]-데칸]-4-일)-페닐포스페이트(CDP-Star)과이나트륨 3(4-메톡시스피로[1,2-디옥세탄-3,2'-(5'-클로로)-트리사이클로-[3,3,33,7]-데칸]-4-일)-페닐 포스페이트 디옥세탄(CSPD)의 성능을 비교하여 나타낸 것이다,
제2도는 화학 발광 증강제, 즉 폴리비닐벤질트리부틸암모늄 클로라이드의 존재가 미치는 영향을 나타낸 것이다,
제3도는 바이오티닐화된 pBR322-35mer에 대한 나일론 멤브레인 분석에 있어서 CSPD 및 CDP-Star을 비교하여 나타내었다,
제4도 및 제5도는 CSPD 및 CDP-Star에 대해 나일론 및 PVDF 멤브레인 상에서 수행된 웨스턴 블롯팅(western blotting)분석의 Kodak XAR-5 필름노출의 재생도이다.

Claims (31)

  1. 일반식(I)의 디옥세탄
    상기식에서 Y1및 Y2는 독립적으로 H, 하이드록실 그룹, 할로겐, 비치환된 저급 알킬 그룹, 하이드록시 저급 알킬 그룹, 할로 저급 알킬 그룹, 페닐 그룹, 할로페닐 그룹, 알콕시 페닐 그룹, 알콕시 페녹시 그룹, 하이드록시 알콕시 그룹, 시아노 그룹, 아미드 그룹, 알콕시 그룹 또는 카복실 그룹이고, R은 C1-12 알킬, 아릴 또는 아르알킬이며, X는 소프페이트, 갈락토사이드, 아세테이트, 1-포스포-2, 3-디아실글리세라이드, 1-티오-D-글루코사이드, 아데노신 트리포스페이트, 아데노신 디소프페이트, 아데노신 모노포스페이트, 아데노신, α-D-글루코사이드, β-글루코사이드, β-D-글루쿠로나이트, α-D-만노사이드, β-D-만노사이드, β-D-프럭토푸라노사이드, β-글루코사이두로네이트, P-톨루엔??설포닐-L-아르기닌 에스테르 및 P-톨루엔설포닐-L-아르기닌 아미드로 구성된 그룹 중에서 선택된 효소-불안정성 그룹이고, Z는 전자 흡인 그룹 및 전자 공여그룹으로 구성된 중에서 선택된 전자-활성그룹이며, 페닐 환상에서 4또는 5위치를 차지한다.
  2. 제1항에 있어서, Z가 C1, OM, OAr, NM3 +, NHCOM, NHCOM1, NHCO-Ar, NHCOOAr, NHCOOM, NHCOOM1, CM3, NO2, COOM, COOAr, NHSO2OM, NHSO2Ar, CF3, Ar, M, SiM3, SiAr2, SiArM2, SO2NHCOM, SO2NHCOAr, SO2M, SO2Ar, SM 및 SAr로 구성된 그룹 중에서 선택되고, M 및 M1은 독립적으로 C1-6 알킬이며, Ar은 페닐 도또는 나프틸인 디옥세탄.
  3. 제2항에 있어서, Z가 클로로, 메톡시 또는 아미도 치환체이고, 5위치를 차지하는 디옥세탄.
  4. 제3항에 있어서, Z가 염소인 디옥세탄.
  5. 제4항에 있어서, Y2가 수소이고 Y1은 염소인 디옥세탄.
  6. 제2항에 있어서, Z가 에톡시 또는 염소이고, 4위치를 차지하는 디옥세탄.
  7. 제6항에 있어서, Z가 연소이고, Y2는 수소이며, Y1은 염소인 디옥세탄.
  8. 제2항에 있어서, Z가 5위치를 차지하며, 메톡시이고, Y2는 수소이며, Y1은 염소인 디옥세탄.
  9. 제5항, 7항 또는 8항에 있어서, X가 포스페이트 잔기인 디옥세탄.
  10. 제9항에 있어서, R이 C1-4 알킬인 디옥세탄.
  11. 제1항에 있어서, Y2가 수소이고, Y1은 염소이며, Z는 -OCH3이고 5위치를 차지하며, R은 메틸이고, X는 포스페이트인 디옥세탄.
  12. 제1항에 있어서, Y2가 수소이고, Y1은 염소시며, Z는 염소이고 5위치를 차지하며, R은 메틸이고, X는 포스페이트인 디옥세탄.
  13. 제1항에 있어서, Y2가 수소이고, Y1은 염소시며, Z는 염소이고 4위치를 차지하며, R은 메틸이고, X는 포스페이트인 디옥세탄.
  14. 일반식(II)또는 (III)의 디옥세탄.
    상기식에서, Y1및 Y2는 독립적으로 H, 하이드록실 그룹, 할로겐, 비치환된 저급 알킬 그룹, 하이드록시 저급 알킬 그룹, 할로 저급 알킬 그룹, 페닐 그룹, 할로페닐 그룹, 알콕시 페녹시 그룹, 알콕시 페닐 그룹, 하이드록시 알콕시 그룹, 시아노 그룹, 아미드 그룹, 알콕시 그룹 또는 카복실 그룹이고, R은 C1-12 알킬, 아릴 또는 아르알킬이며, X는 포스페이트, 갈락토사이드, 아세테이트, 1-포스트-2, 3-디아실글리세라이드, 1-티오-D-글루코사이드, 아데노신 트리포스페이트, 아데노신 디포스페이트, 아데노신 모노포스페이트, 아데노신, α-D-글루코사이드, β-D-글루코사이드, β-D-글루쿠로나이드, α-D-만노사이드, β-D-만노사이드, β-D-프럭토푸라노사이드, β-글루코사이두로네이트, P-톨루엔설포닐-L-아르기닌 에스테르 및 P-톨루엔설포닐-L-아르기닌 아미드로 구성된 그룹 중에서 선택된 효소-불안정성 그룹이고, Z는 전자 흡인 그룹 및 전자 공여 그룹으로 구성된 중에서 선택된 전자-활성그룹이며, OX는 치환점 에서의 탄소를 포함한, 디옥세탄 상의 나프틸 환의 치환점과 치환점에서의 탄소를 포함한, OX의 치환점 사이의 환 탄소의 수가 홀수가 되도록 나프틸 환 상에서 치환되고, Z는 디옥세탄 환 상의 치환점에서 인접한 위치를 제외하고는 어떠한 환탄소 상에서도 치환된다.
  15. 제14항에 있어서, Z가 C1, OM, OARr, NM3 +, NHCOM, NHCOM1, NHCOAr, NHCOOAr, NHCOOM, NHCOOM1, NHCOOM1, CM3, NO2, COOM, COOAr, NHSO2OM, NHSO2Ar, CF3, Ar, M, SiM3, SiAr2, SiArM2, SO2NHCOM, SO2NHCOAr, SO2M, SO2Ar, SM 및 SAr로 구성된 그룹 중에서 선택되고, M은 M1은 독립적으로 C1-6 알킬이며, Ar은 페닐 또는 나프틸인 디옥세탄.
  16. 제14항에 있어서, Z가 클로로, 메톡시 또는 아미도 치환체이고, 4,5-또는 6위치를 차지하는 디옥세탄.
  17. 제1항 또는 14항의 디옥세탄 및 수용액 중에서 이 디옥세탄의 X부위를 분해시킬 수 있는 효소를 포함하는, 화학 발광성 디옥세탄 리포터 분자를 사용하여 분석을 수행하기 위한 키트.
  18. 제17항에 있어서, 수용액에서 X부위의 분해시 디옥세탄으로 부터 수득되는 화학 발광 시그날을 증가시키는 증진 물질을 추가로 포함하는 키트.
  19. 제17항에 있어서, 상기 분석이 면역 분석이고, 효소가 분석을 수행하여 존재 또는 농도를 검출하고자 하는, 분석물질에 결합할 수 있는 제제와 복합제를 이루는 키트.
  20. 제17항에 있어서, 분석이 DNA프로브 분석이며, 이러한 분석을 수행할 수 있는 멤브레인을 추가로 포함하는 키트.
  21. 제17항에 있어서, 수용액에서 X부위의 분해시 디옥세탄으로 부터 수득되는 화학 발광 시그날을 증가시키는 증진 물질을 추가로 포함하는 키트.
  22. 제20항에 있어서, 효소가 분석을 수행하여 존재 또는 농도를 검출하고자 하는, 샘플에 존재하는 분석물질과 복합제체를 이룰 수 있는 제제와 복합제를 이루은 키트.
  23. 제17항에 있어서, 분석이 DNA 서열 분석이며, 이러한 서열 분석을 수행할 수 있는 멤브레인을 추가로 포함하는 키트.
  24. 제23항에 있어서, 수용액에서 X부위의 분해시 디옥세탄으로 부터 수득되는 화학 발광 시그날을 증가시키는 증진 물질을 추가로 포함하는 키트.
  25. 제23항에 있어서,효소가 분석하여 서열을 결정하고자 하는 DNA에 효소를 결합시킬 수 있는 제제와 복합제를 이루는 키트.
  26. 하기 일반식의 화합물.
    상기식에서, Q1은 CHO, CH(OCH3)2또는 COOM이고, Q2는 OH, OM(CH3)3CCOO- 또는 OSiM3이고, Q3는 Cl, Br, F, NO2또는 NH2이며, M은 탄소수 1내지 6의 알킬 또는 아르알킬이다.
  27. 샘플을 제1항 또는 14항의 디옥세탄과 접촉시켜 샘플내에 존재하는 효소가 효소-불안정성 그룹 X를 분해 시키도록 하고 이로 인한 광 방출을 검출함(여기에서 방출하는 광의 검출은 샘플내에 효소가 존재함을 시사하는 것이다)을 특징으로 하여 샘플내의 효소의 존재를 검출하는 방법.
  28. 제27항에 있어서, X그룹이 포스페이이트이고, 효소가 알카리성 포스파타제인 방법.
  29. 임의로 제1항 또는 14항의 디옥세탄을 디옥세탄의 효소-불안정성 그룹 X를 분해시키는 효소와 반응시켜(여기에서 효소는 특이적 결합쌍의 제2멤버와 복합체를 이룬다)생성된 화학 발광을 검출함을 특징으로 하여 제1 및 제2멤버를 갖는 특이적 결합쌍의 제1멤버를 검출하는 방법.
  30. 제29항에 있어서, 면역 분석인 방법.
  31. 제29항에 있어서, 핵산 프로브 분석인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950700026A 1993-05-07 1995-01-05 Improved chemilluminescent 1,2-dioxetanes KR0154209B1 (en)

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US057903 1993-05-07
US08/057,903 US5538847A (en) 1989-07-17 1993-05-07 Chemiluminescent 1,2-dioxetanes
US231673 1994-04-25
US08/231,673 US5582980A (en) 1989-07-17 1994-04-25 Chemiluminescent 1,2-dioxetanes
PCT/US1994/004555 WO1994026726A1 (en) 1993-05-07 1994-05-06 Improved chemiluminescent 1,2-dioxetanes

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US5840919A (en) 1998-11-24
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FI950075A (fi) 1995-01-05
EP1120423B1 (en) 2007-03-14
AU6774194A (en) 1994-12-12
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AU2474997A (en) 1997-08-14
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ATE334996T1 (de) 2006-08-15
US5582980A (en) 1996-12-10
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ATE356822T1 (de) 2007-04-15
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US5851771A (en) 1998-12-22
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