The Synthesis of Acridine-9-Ethylamine

Jensen, H.; Howland, L. H.

doi:10.1021/ja01418a029

Cited by 11 publications

(4 citation statements)

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“…The acridine-CPG supports (9a and 9b) were prepared from trans-4-hydroxy-L-prolinol (2) and the appropriate acridinylpropionic or -pentanoic acid TFP ester (6a or 6b), as shown in Scheme III. The 9-acridinylalkanoic acids can be prepared with a variety of alkyl chain lengths by heating the corresponding aliphatic diacid with diphenylamine and zinc chloride (23). For example, 45 g (16% 11b (n = 3) yield) of 5-(9-acridinyl)pentanoic acid were obtained from the condensation reaction with adipic acid.…”

Section: Resultsmentioning

confidence: 99%

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Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotides

Ad²,

Js³

et al. 1991

Bioconjugate Chem.

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New solid supports are described which allow the direct synthesis of oligonucleotides bearing either cholesterol or acridine at the 3'-terminus. A stereochemically defined amino diol was prepared by reduction of N-Cbz-hydroxy-L-proline. This linker molecule was first acylated with the desired conjugate molecule, then protected as the dimethoxytrityl ether. The remaining secondary hydroxyl group was succinylated and immobilized on a controlled-pore glass support. 3'-Modified oligodeoxynucleotides (ODNs) were prepared from these supports by using standard phosphoramidite coupling and deprotection conditions. A cholesterol-modified support was prepared from cholesterol chloroformate and the amino diol linker. Two types of acridine-modified solid supports were prepared from acridine tetrafluorophenyl esters with linker arms of different length. In an alternative synthesis of 3'-derivatized ODNs, these active esters were also utilized for acylation of a 3'-amine-modified ODN. A thermal denaturation study was done to determine the effect of the different linker arms on hybridization to a complementary ODN target. Facile synthesis and purification of the 3'-modified ODNs makes these functionalized solid supports especially useful for preparation of oligonucleotides bearing these and other modifications.

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Section: Resultsmentioning

confidence: 99%

“…2.3.5.6-Tetrafluorophenyl 3-(9-Acridinyl)propionate (6a). To a solution of 400 mg (1.59 mmol) of 3-(9acridinyl)propionic acid (23) and 0.22 mL of triethylamine in 20 mL of methylene chloride was added 496 mg (1.75 mmol) of FMPT. The mixture was stirred at room temperature for 15 min.…”

Section: Methodsmentioning

confidence: 99%

Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotides

Ad²,

Js³

et al. 1991

Bioconjugate Chem.

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“…Syntheses. The preparation of 3-(9-acridinyl)propionic acid was described by Jensen and Howland (10). Its quarternization was accomplished by heating 1.0 g with 0.60 g of methyl iodide in a sealed glass tube for 4 h at 130 °C.…”

Section: Methodsmentioning

confidence: 99%

Optical sensor for continuous determination of halides

Urbano¹,

Offenbacher²,

Wolfbeis³

1984

Anal. Chem.

126

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% % % % P found Cu found, corrected, certified, 0.098 0.017 0.095 0.095 0.041 8j 36 2 0.148 0.486 0.044 a Correction factor = 0.213 ppm P/ppm Cu.-_ _ _ l -l _ _ _ _ _ _ 1 1 --~prominent Fe line shown in Figure 8 was used as the side line, and the reference solutions were matrix matched with the samples to contain 1.00% Fe (w/v). The small Fe peak located approximately 0.005 nm to the long wavelength side of phosphorus does not interfere with the analysis as long as both SLIM and matrix matching are applied. Both P and Cu were determined (at 214.91 nm and 327.40 nm, respectively) and the P results corrected for Cu spectral interference; analytical resulta are shown in Table (1) Floyd, M. A.; Fassel, V. A,; Winge, R. K.; Katzenberger, J. M.; D'Silva, (2) Nygaard, Danton D.; Chase, Duane S.; Lelghty, David A. Appl. Spec-A. P. The first optical sensor for halides and pseudohaildes Is described. It is based on dynamic fluorescence quenchlng of acrldlnlum and qulnoiinlum Indlcators, which were immobilized vla spacer groups onto a glass surface. The sensors are able to indicate the concentration of halides in solution by virtue of the decrease in fluorescence intendty due to the quenching process. The sensltivity toward different halides can-to some extent-be varied by the cholce of the indicator. The method Is increasingly sensitlve on going from chloride to bromide to iodlde. Detection limits are 0.15 mM for iodide, 0.40 mM for bromide, and 10.0 mM for chiorlde. The errors of determination in the concentratlon range from 0.01 to 0.1 M are 1 % for Iodide, 1.5% for bromide, and 3-5% for chloride.The development of sensors based on immobilized fluorescent reagents is a matter of growing interest (1-4). Sensors offer advantages over conventional solution fluorescence measurements, since they allow the determination of concentrations without significantly perturbing the sample. In addition, they can be used for continuous sensing. Fluorescence-optical sensors are based on three fundamental principles: (a) changes in acid-base equilibria of indicators (2,5); (b) reversible formation of fluorescent chelates (3); (c) dynamic fluorescence quenching (4). The first two principles are similar in that they are based on processes that occur in the ground state, whereas the latter occur in the first excited singlet state.In this paper we report the characteristics of a sensor for halides that is based on the dynamic quenching of glass-immobilized heterocyclic indicators 1 and 2, whose structures are shown in the formula scheme.The quenching of quinoline-type fluorophores was first described by Stokes as early as 1869 (6), when he observed that the fluorescence of quinine in dilute sulfuric acid was reduced after addition of hydrochloric acid or halide ions. The involved process is now known to obey the Stern-Volmer equationHere, Fo is the fluorescence intensity of a solution in the absence of a quencher, F is the fluorescence intensity in the presence of a quencher, [Q] is the concentration of the quencher, and Kq is the so-called q...

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“…The synthesis of dye 1 was ®rst described by Wolfbeis and Urbano in 1982 for use as ā uorescent standard in the near neutral pH range [14] and was achieved by fusing acridine with 1,3-propane sultone at 120 C for 2 h with moisture excluded, followed by extraction with DMF and recrystalisation from alcohol. The intermediate for dye 2 was described as early as 1926 by Jensen and Howland [21] (Fig. 2) and its quaternisation with methyl iodide (step 2) followed by counterion exchange with sodium tetraphenylboron to produce the borate salt, in 1984 by Urbano et al [5].…”

Section: Dye Synthesismentioning

confidence: 99%

Quenching of Fluorescence

2006

Principles of Fluorescence Spectroscopy

221

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Two halide sensitive acridinium¯uorophores have been synthesised and immobilised in a hydrophilic copolymer. Thin ®lms of the copolymers swell in aqueous media allowing dye¯uorescence to be dynamically quenched by the di usion of halide ions. The new sensor ®lms have been characterised in terms of their sensitivity and selectivity towards halide and are compared to ®lms containing both bound and unbound Rhodamine B. The sensor ®lms are reversibly capable of determining halide ions at mildly alkaline pH with typical 90% response times of % 1±2 min. The sensor ®lms are cheap to produce, can readily be coated on disposable glass microscope slides or on the tip of a ®bre optic bundle and have a shelf life in excess of 2 years. #

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The Synthesis of Acridine-9-Ethylamine

Cited by 11 publications

References 0 publications

Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotides

Acridine- and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotides

Optical sensor for continuous determination of halides

Quenching of Fluorescence

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