Synthesis of [3H,33P]‐phosphoramide and ‐isophosphoramide mustards and metabolites [3H]‐chloroethylaziridine and ‐aziridine for studies of DNA alkylation

Springer, James B.; Colvin, O. Michael; Ludeman, Susan M.

doi:10.1002/jlcr.1157

Cited by 3 publications

(3 citation statements)

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“…The preparation and characterization of β , β ′‐dimercaptodiethyl ether was consistent with those in the literature reported by us (21). Bis(2‐chloroethyl)amine hydrochloride and 1‐oxa‐4,7‐dithia‐10‐azacyclododecane were prepared according to the literatures (39–42). Sensor 1 consisted of a dansyl moiety and azathia‐crown ether was synthesized by the amide reaction of 1‐oxa‐4,7‐dithia‐10‐azacyclododecane and dansyl chloride in a 55% yield.…”

Section: Resultsmentioning

confidence: 99%

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A highly selective fluorescent sensor for mercury ion (II) based on azathia‐crown ether possessing a dansyl moiety

et al. 2010

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An intramolecular charge transfer (ICT) fluorescent sensor 1 using a dansyl moiety as the fluorophore and an azathia-crown ether as the receptor was designed, synthesized and characterized. The ions-selective signaling behaviors of the sensor 1 were investigated in CH(3) CN-H(2) O (1:1, v/v) by fluorescence spectroscopy. It exhibited remarkable fluorescence quenching upon addition of Hg(2+), which was attributed to the 1:1 complex formation between 1 and Hg(2+), while other selected metal ions induced basically no spectral changes. The sensor 1 showed a rapid and linear response towards Hg(2+) in the concentration range from 5.0 × 10(-7) to 1.0 × 10(-5) mol L(-1) with the detection limit of 1.0 × 10(-7) mol L(-1). Furthermore, the whole process could be carried out in a wide pH range of 2.0-8.0 and was not disturbed by other metal ions. Thus, the sensor 1 was used for practical determination of Hg(2+) in different water samples with satisfactory results.

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Section: Resultsmentioning

confidence: 99%

“…: 110°C (15 mmHg). 1 (39,40). Diethanolamine (21.9 g, 0.21 mol) was dissolved in chloroform (30 mL) in a 250 mL three-necked round-bottomed flask keeping the temperature at 0°C.…”

Section: Synthesismentioning

confidence: 99%

A highly selective fluorescent sensor for mercury ion (II) based on azathia‐crown ether possessing a dansyl moiety

et al. 2010

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“…This kind of compound is usually synthesized by hydrolysis of the corresponding phosphorodiamidyl chloride [20,40]. In all our attempts, this methodology appeared not reliable and we decided to focus our attention to a two-steps sequence involving synthesis of the corresponding benzyl ester followed by hydrogenation as described in the literature [52] and leading to IPM in 80% overall yield (supporting data). However, Mitsunobu conditions between IPM and 10-BH3 led to a poor yield of the desired product 14c-BH3 (5%) while a large amount of starting material 10-BH3 (76%) has been recovered.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis and evaluation of targeted hypoxia-activated prodrugs applied to chondrosarcoma chemotherapy

Gerard

Voissière

Peyrode

et al. 2020

Bioorganic Chemistry

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The tumor microenvironment in chondrosarcoma (CHS), a chemo-and radio-resistant cancer provides unique hallmarks for developing a chondrosarcoma targeted drug-delivery system. Tumor targeting could be achieved using a quaternary ammonium function (QA) as a ligand for aggrecan, the main high negative charged proteoglycan of the extracellular matrix of CHS, and a 2-nitroimidazole as trigger that enables hypoxia-responsive drug release. In a previous work, ICF05016 was identified as efficient proteoglycan-targeting hypoxia-activated prodrug in a human extraskeletal myxoid chondrosarcoma model in mice and a first study of the structureactivity relationship of the QA function and the alkyl linker length was conducted. Here, we report the second part of the study, namely the modification of the nitro-aromatic trigger and the position of the proteoglycan-targeting ligand at the aromatic ring as well as the nature of the alkylating mustard. Synthetic approaches have been established to functionalize the 2nitroimidazole ring at the N-1 and C-4 positions with a terminal tertiary alkyl amine, and to perform the phosphorylation step namely through the use of an amine borane complex, leading to phosphoramide and isophosphoramide mustards and also to a phosphoramide mustard bearing four 2-chloroethyl chains. In a preliminary study using a reductive chemical activation, QA-conjugates, except the 4-nitrobenzyl one, were showed to undergo efficient cleavage with release of the corresponding mustard. However N,N,N-trimethylpropylamimium tethered to the N-1 or C-4 positions of the imidazole seemed to hamper the enzymatic reduction of the prodrugs and all tested compounds featured moderate selectivity toward hypoxic cells, likely not sufficient for application as hypoxia-activated prodrugs.

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Radiochemistry

Urch

2008

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This year's report on recent progress in Radiochemistry considers radiochemical methods in isotope production, advances in labelling procedures, radioactive isotopes in the environment and miscellaneous topics of radiochemical interest. Radiation chemistry, neutron activation analysis and the chemistry of elements that happen to be radioactive will be eschewed. HighlightsThe labelling of glucose 91 with oxygen-15!-from cyclotron to product in just seven minutes. A solution to part of nuclear waste problem by transmutation of technetium 381 into a stable ruthenium isotope. And the possibility of varying 46 radioactive half-lives by chemical means-to be confirmed.

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Synthesis of [³H,³³P]‐phosphoramide and ‐isophosphoramide mustards and metabolites [³H]‐chloroethylaziridine and ‐aziridine for studies of DNA alkylation

Cited by 3 publications

References 9 publications

A highly selective fluorescent sensor for mercury ion (II) based on azathia‐crown ether possessing a dansyl moiety

A highly selective fluorescent sensor for mercury ion (II) based on azathia‐crown ether possessing a dansyl moiety

Design, synthesis and evaluation of targeted hypoxia-activated prodrugs applied to chondrosarcoma chemotherapy

Radiochemistry

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