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首页> 外文期刊>Chemistry: A European journal >Photostable, amino reactive and water-soluble fluorescent labels based on sulfonated rhodamine with a rigidized xanthene fragment
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Photostable, amino reactive and water-soluble fluorescent labels based on sulfonated rhodamine with a rigidized xanthene fragment

机译：基于磺化罗丹明的硬质x吨片段的光稳定性，氨基反应性和水溶性荧光标记

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Highly water soluble fluorescent dyes were synthesized and transformed into new amino reactive fluorescent labels for biological microscopy. To this end, rhodamine 8 (prepared from 7-hydroxy-1,2,3,4-tetrahydroquinoline (7) and phthalic anhydride in 85% aq. H3PO4) was sulfonated with 30% SO3 in H2SO4 and afforded the water soluble disulfonic acid 3a (64%). Amidation of the carboxy group in 3a with 2-(methylamino)ethanol in the presence of O-(7-azabenzotriazol-1-yl)- N,N,N',N'-tetramethyluronium-PF6-(HATU) led to alcohol 3b (66%) which was transformed into the amino reactive mixed carbonate 3d with di(N-succinimidyl)carbonate and Et3N. Reaction of the carboxy group in 3a with MeNH(CH2)(2)CO2Me and N,N,N',N'-tetramethyl-O-(N-succinimidyl)-uronium center dot BF4- (TSTU) yielded methyl ester 13. After saponification of the aliphatic carboxy group in 13, the compound was converted into NHS-ester 3e (using HATU and Et3N). Heating of 7 with trimellitic anhydride in H3PO4 gave a mixture of dicarboxylic acids 14 and 15 (1:1). Regioisomer 15 was isolated, sulfonated with 30% SO3 in H2SO4, and disulfonic acid 3f was used for the synthesis of the mono NHS-ester 3g, in which the sterically unhindered carboxy group was selectively activated (with N-hydroxysuccinimide, HATU, and Et3N). The sulfonated rhodamines 3b, c and f are soluble in water (up to 0.1 M), have excellent photostabilities and large fluorescence quantum yields. Subdiffraction resolution images of tubulin filaments of mammalian cells stained with these dyes illustrate their applicability as labels for stimulated emission depletion microscopy and other fluorescence techniques.
机译：合成了高度水溶性的荧光染料，并将其转化为用于生物显微镜的新的氨基反应性荧光标记。为此，将罗丹明8（由7-羟基-1,2,3,4-四氢喹啉（7）和邻苯二甲酸酐在85％的H3PO4水溶液中制得）用在H2SO4中的30％SO3磺化，得到水溶性二磺酸3a（64％）。在O-（7-氮杂苯并三唑-1-基）-N，N，N'，N'-四甲基铀-PF6-（HATU）存在下，用2-（甲基氨基）乙醇将3a中的羧基酰胺化，生成醇3b（66％）与二（N-琥珀酰亚胺基）碳酸酯和Et 3 N转化为氨基反应性混合碳酸酯3d。 3a中的羧基与MeNH（CH2）（2）CO2Me和N，N，N'，N'-四甲基-O-（N-琥珀酰亚胺基）-铀中心点BF4-（TSTU）反应生成甲酯13。将13中的脂肪族羧基皂化后，将化合物转化为NHS-酯3e（使用HATU和Et3N）。将7与偏苯三酸酐在H3PO4中加热，得到二羧酸14和15（1：1）的混合物。分离出区域异构体15，在H2SO4中用30％SO3磺化，然后使用二磺酸3f合成单NHS-酯3g，其中选择性地激活了空间不受阻碍的羧基（用N-羟基琥珀酰亚胺，HATU和Et3N ）。磺化罗丹明3b，c和f可溶于水（至多0.1 M），具有出色的光稳定性和大的荧光量子产率。用这些染料染色的哺乳动物细胞微管蛋白细丝的亚衍射分辨率图像说明了它们作为受激发射耗竭显微镜和其他荧光技术的标记物的适用性。

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