Petersen M, Hamed A A, Pedersen E B, Jacobsen J P
Department of Chemistry, Odense University, Odense M, DK-5230 Denmark.
Bioconjug Chem. 1999 Jan-Feb;10(1):66-74. doi: 10.1021/bc980073w.
The thiazole orange dye 1,1'-(4,4,8,8-tetramethyl-4, 8-diazaundecamethylene)-bis-4-[(3-methyl-2,3-dihydro-2(3H)-benzo-1 ,3-thiazolylidene)methyl]quinolinium tetraiodide (TOTO) binds to double-stranded DNA (dsDNA) in a sequence selective bis-intercalation. We have examined the binding of derivatives of TOTO with different substituents on the benzothiazole ring. The analogues are the following: 1,1'-(4,4,8,8-tetramethyl-4, 8-diazaundecamethylene)-[4-[3-(benzyl-2, 3-dihydro-2-(3H)-benzothiazolylidene)methyl]quinolinium]-[4-[3-(++ +methy l-2, 3-dihydro-2-(3H)-benzothiazolylidene)methyl]quinolinium]tetraio dide (TOTOBzl) and 1,1'-(4,4,8,8-tetramethyl-4, 8-diazaundecamethylene)-bis-4-[(3-ethyl-2,3-dihydro-2(3H)-benzo-1, 3-thiazole)methyl]quinolinium tetraiodide (TOTOEt). In this paper, we report the synthesis of TOTOBzl and TOTOEt together with the one- and two-dimensional 1H NMR investigations of complexes between these TOTO analogues and the dsDNA oligonucleotide d(CGCTAGCG)2. Both analogues yield extremely stable complexes in which each chromophore is sandwiched between two base pairs in a (5'-CpT-3'):(5'-ApG-3') site. The linker spans over two base pairs in the minor groove. The benzyl group in TOTOBzl and the ethyl groups in TOTOEt is pointing outward in the major groove.
噻唑橙染料1,1'-（4,4,8,8-四甲基-4,8-二氮杂十一亚甲基）-双-4-[(3-甲基-2,3-二氢-2(3H)-苯并-1,3-噻唑亚基)甲基]喹啉四碘化物（TOTO）以序列选择性双插入的方式与双链DNA（dsDNA）结合。我们研究了在苯并噻唑环上具有不同取代基的TOTO衍生物的结合情况。类似物如下：1,1'-（4,4,8,8-四甲基-4,8-二氮杂十一亚甲基）-[4-[3-(苄基-2,3-二氢-2-(3H)-苯并噻唑亚基)甲基]喹啉]-[4-[3-(++ +甲基-2,3-二氢-2-(3H)-苯并噻唑亚基)甲基]喹啉]四碘化物（TOTOBzl）和1,1'-（4,4,8,8-四甲基-4,8-二氮杂十一亚甲基）-双-4-[(3-乙基-2,3-二氢-2(3H)-苯并-1,3-噻唑)甲基]喹啉四碘化物（TOTOEt）。在本文中，我们报告了TOTOBzl和TOTOEt的合成，以及这些TOTO类似物与dsDNA寡核苷酸d(CGCTAGCG)2之间复合物的一维和二维1H NMR研究。两种类似物都形成了极其稳定的复合物，其中每个发色团夹在(5'-CpT-3'):(5'-ApG-3')位点的两个碱基对之间。连接子横跨小沟中的两个碱基对。TOTOBzl中的苄基和TOTOEt中的乙基指向大沟外侧。
