ChemInform Abstract: Synthesis of Steroidal Phthalimidoaziridines.

Shafiullah, Shafiullah; Shamsuzzaman, Shamsuzzaman; Ansari, J. A.

doi:10.1002/chin.198847305

Cited by 2 publications

(8 citation statements)

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“…After repeated crystallization and purity, identity and stability of the compound was confirmed by elementary analysis and by IR, NMR and massspectra (5). Thin layer chromatography indicated that the test steroid was chromatographically homogenous.…”

Section: R Imentioning

confidence: 96%

“…The structure of aziridinyl steroid, 313-acetoxy 5~-cholestano [5,6]N-phthalmidoaziridine, used in this study is shown below:…”

Section: Steroidmentioning

confidence: 99%

“…The steroid was synthesized by Shafiullah et al (5). After repeated crystallization and purity, identity and stability of the compound was confirmed by elementary analysis and by IR, NMR and massspectra (5).…”

Section: R Imentioning

confidence: 99%

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Aziridinyl steroid‐induced lesions in DNA and apoptosis in promyelocytic leukemia cells

et al. 1997

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SUMMARY :Variety of synthetic steroids are reported to be mutagenic as well as carcinogenic. The mutagenic and carcinogenic nature of these compounds have been related to their potential of being reactive to genetic material and production of reactive oxygen species. Here we have analyzed the action of aziridinyl steroid on calf thymus DNA and human promyelocytic leukemia cell line HL-60 under in vitro conditions. Calf thymus DNA when treated with various doses of aziridinyl steroid induced a high degree of strand separation and sensitivity/susceptibility to S1 nuclease hydrolysis. The treatment also induced an increasing number of strand breaks per molecule of DNA as determined by alkaline unwinding assay. Relatively higher doses of steroid, however, displayed a reduced susceptibility to Sx nuclease hydrolysis and did not increase the number of strand breaks in DNA. Moreover, the high dose treatments result increased melting temperature and an enhanced rate of reanealing atter thermal denaturation, indicating that interstrand crosslinks are induced at higher doses of steroid treatment. Moreover, steroid treatment caused cell death in human promyelocytic leukemia cell line HL-60 and induced DNA degradation, characteristic of apoptosis. The test steroid has the ability to produce reactive oxygen intermediates (ROI) as determined by chemical methods. Incorporation of oxygen radical scavengers into the system blocked the damaging effect of steroid in calf thymus DNA and HL-60 cells. These observations strongly suggest that aziridinyl steroid, a pharmaceutical, damages mammalian DNA and induces apoptosis by the production of ROI in the test system.

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Section: R Imentioning

confidence: 96%

“…The structure of aziridinyl steroid, 313-acetoxy 5~-cholestano [5,6]N-phthalmidoaziridine, used in this study is shown below:…”

Section: Steroidmentioning

confidence: 99%

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Aziridinyl steroid‐induced lesions in DNA and apoptosis in promyelocytic leukemia cells

et al. 1997

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“…In dichloromethane the product ratio is approx. 1 : 1, whereas the alcohol (37) predominates after oxidation in chloroform or pyridine.…”

Section: 21 Electrophilic Additionmentioning

confidence: 99%

“…25 Cholesteryl acetate gives nearly pure (> 99 YO) 5P,6P-epoxide, although cholesterol itself does not react. Photo-oxygenation of cholesterol in the presence of titanium tetraisopropoxide provides a convenient route to the epoxyalcohols (37) and (38). 26 Oxygen transfer in the intermediate cholesterol hydroperoxide takes place much faster than radical promoted OR *\ isomerization.…”

Section: 21 Electrophilic Additionmentioning

confidence: 99%

Steroids: reactions and partial synthesis

Turner¹

1991

Nat. Prod. Rep.

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ChemInform Abstract: Synthesis of Steroidal Phthalimidoaziridines.

Cited by 2 publications

References 0 publications

Aziridinyl steroid‐induced lesions in DNA and apoptosis in promyelocytic leukemia cells

Aziridinyl steroid‐induced lesions in DNA and apoptosis in promyelocytic leukemia cells

Steroids: reactions and partial synthesis

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