The solubilization of polycyclic aromatic hydrocarbons by purines

Weil‐Malherbe, H.

doi:10.1042/bj0400351

Cited by 145 publications

(22 citation statements)

References 6 publications

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“…From these experiments certain types of interaction have been suggested between hydrocarbons and DNA. In view of the pioneer work of Weil-Malherbe as to the solubilization of the aromatic hydrocarbons in purines, 8 it has been supposed that the active sites solubilizing the aromatic hydrocarbons in DNA are the bases, especially purines. The molecular complex between the aromatic hydrocarbons and base analog, i.e., tetramethyluric acid, which has been verified by x-ray analysis9 gives additional support to this proposition.…”

Section: Introductionmentioning

confidence: 99%

Interaction of polynuclear aromatic hydrocarbons, 4‐nitroquinoline 1‐oxides, and various dyes with DNA

Nagata¹,

Kusumoto²,

Tagashira³

et al. 1966

Biopolymers

129

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SynopsisBy using the flow dichroism method, in vitro interaction of the aromatic polynuclear hydrocarbons with calf thymus DNA was studied. A clear dichroism of the hydrocarbons which interacted with DNA was observed, showing a specific type of interaction. Hydrocarbons were classified into two groups, depending on whether the orientation is parallel or perpendicular to the direction of flow. 3,CBenzopyrene, pyrene, and phenanthrerie belong to the first group, and the second group contains 2Gmethylcholanthrene, tetracene, pentacene, and coronene. 4Nitroquinoline l-oxide (CNQO) and its derivatives have also been found to be oriented parallel to the planes of bases of DNA, and a distinct parallel was found between the amount of binding and carcinogenicity. Base specificity of binding of 4-NQO with DNA W B I~ studied, and purines were suggested to be active sites of interaction. Actinomycin D, several acridine dyes, and methylene blue etc. were found to be oriented parallel to the planes of DNA bases, and in the ca..es of acridine dyes this finding does not contradict the intercalation mechanism proposed by Lerman.

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Section: Introductionmentioning

confidence: 99%

Interaction of polynuclear aromatic hydrocarbons, 4‐nitroquinoline 1‐oxides, and various dyes with DNA

Nagata¹,

Kusumoto²,

Tagashira³

et al. 1966

Biopolymers

129

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“…1) found early interest for various reasons. The solubility of polycyclic arenes in water, e. g. of the carcinogenic 3,4-benzopyrene, is increased by 1 [13]. Studies of the complex with benzene revealed the usual problems [14] and were finally [15] interpreted by the formation of both 1:1 and 1:2 complexes.…”

Section: Introductionmentioning

confidence: 97%

Molecular Complexes, 14. Isomeric Arene Complexes of Caffeine and 1,3,7,9-Tetramethyluric Acid Detected with Toluene. Polar Interactions Inverted with Hexafluorobenzene

Stamm

Jäkel

Stafe

2003

Zeitschrift Für Naturforschung B

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Stacking of an arene D on caffeine (1) near 7-Me and 8-H is known ( 1 H NMR shifts, CCl 4 , AUS concept) to yield the same association constant K for each signal of 1. Toluene (T) and 1 now yielded the same K from 7-Me and 8-H while K from 1-Me (and 3-Me) is smaller indicating a minor stacking centre near N-1 that forms both 1T and 1T 2 ; this 1T 2 disturbs computations of K. The main stacking centre forms no 1T 2 since its 1T is stabilized by dipole-dipole interaction. Diphenylmethane Dp, a substituted T that cannot form a dimer of type T 2 , does not form 1Dp 2 . Ethyl of 1-ethyltheobromine (2) is proven to stand perpendicular so that the above minor complex can only arise on one face of 2 halving K minor and making the disturbance of computations by 2T 2 insignificant; apart from this minor 2T there are cis-trans isomers of the main complex. Stacking of 1 and 2 with larger arenes is discussed in terms of relative molecular sizes under consideration of the perpendicularly placed ethyl group of 2. Stacking of D near N-3 and N-9 of 1,3,7,9-tetramethyluric acid (4) is known. 4 and T now provided K = 0.218 l mol −1 from 3-Me and 9-Me but K = 0.157 l mol −1 from 1-Me and 7-Me. This and the complex induced shifts IK indicate formation of stacking 4T + 4T 2 and of two edge-on 4T standing on 3-Me and 9-Me under dipole-dipole interaction with a neighbouring oxygen. The oxygens of 4 (and probably of 1, too) form edge-on complexes with hexafluorobenzene; this underlines the importance of polar effects.

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“…However, the extraction efficiency did not seem to correlate with dielectric constant or p6larity and it was thought that the aromaticity of the toluene molecule may have effected this high extraction efficiency in a manner related to the mechanism by which purines are believed to solubilize polycyclic aromatic molecules (Weil-Malherbe, 1946).…”

Section: Standard Curvementioning

confidence: 99%

Assay of 6‐thioguanine in human plasma.

Dooley¹,

Maddocks²

1980

Brit J Clinical Pharma

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1. A fluorimetric method has been developed for measuring therapeutic concentrations of 6‐thioguanine in human plasma. The drug was measured as an oxidized derivative, guanine 6‐sulphonate. 2. 6‐thioguanine was extracted from plasma by a novel procedure which isolated the drug from an interfering plasma components. This method involved the formation of the thioguanine phenyl mercury derivative in alkaline plasma and its extraction into toluene. The free drug was released by back‐extraction into hydrochloric acid. 3. The assay is specific and shows a limit of sensitivity of 5 ng/ml. This was shown to be adequate for measuring plasma concentrations of 6‐thioguanine after the administration of a 160 mg dose in a patient with leukaemia.

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The solubilization of polycyclic aromatic hydrocarbons by purines

Cited by 145 publications

References 6 publications

Interaction of polynuclear aromatic hydrocarbons, 4‐nitroquinoline 1‐oxides, and various dyes with DNA

Interaction of polynuclear aromatic hydrocarbons, 4‐nitroquinoline 1‐oxides, and various dyes with DNA

Molecular Complexes, 14. Isomeric Arene Complexes of Caffeine and 1,3,7,9-Tetramethyluric Acid Detected with Toluene. Polar Interactions Inverted with Hexafluorobenzene

Assay of 6‐thioguanine in human plasma.

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