Novel class of cyclophosphamide prodrug: Cyclophosphamide spiropiperaziniums (CPSP)

Sun, Qi; Li, Runtao; Guo, Wei; Cui, Jinshi; Cheng, Tanyu; Zhang, Ge

doi:10.1016/j.bmcl.2006.04.049

Bioorganic & Medicinal Chemistry Letters

2006

DOI: 10.1016/j.bmcl.2006.04.049

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Novel class of cyclophosphamide prodrug: Cyclophosphamide spiropiperaziniums (CPSP)

Qi Sun¹,

Runtao Li²,

Wei Guo³

et al.

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Cited by 13 publications

(2 citation statements)

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“…A toxicological study showed that the LD 50 of SLXM-2 was 1202.0 AE 27.0 mg/kg which was three times higher than that for CP (387.4 AE 33.8 mg/kg ip). 7 The pharmokinetic mechanism of SLXM-2 inhibiting the growth of H22 cells and the pharmacokinetics has been studied by our group. 8,9 From these results, it appeared that SLXM-2 had similar antitumor activity and much lower toxicity than CP indicating that SLXM-2 could be used as a potential anticancer drug.…”

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“…Although the anticancer activity of SLXM‐2 was slightly weaker than that of CP, it did not significantly cause any body weight loss. A toxicological study showed that the LD 50 of SLXM‐2 was 1202.0 ± 27.0 mg/kg which was three times higher than that for CP (387.4 ± 33.8 mg/kg ip) 7. The pharmokinetic mechanism of SLXM‐2 inhibiting the growth of H22 cells and the pharmacokinetics has been studied by our group 8, 9.…”

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Gas‐fragmentation study of the novel synthetic zwitterionic drug 3‐methyl‐9‐(2‐oxa‐2λ5‐2H‐1,3,2‐oxazaphosphorine‐2‐cyclohexyl)‐3,6,9‐triazaspiro[5,5]undecane chloride (SLXM‐2) by electrospray ionization tandem mass spectrometry

Wang

Song

Wang

et al. 2010

Rapid Comm Mass Spectrometry

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The zwitterionic drug 3-methyl-9-(2-oxa-2lambda5-2H-1,3,2-oxazaphosphorine-2-cyclohexyl)-3,6,9-triazaspiro[5,5]undecane chloride (SLXM-2) is a novel synthetic compound which has shown anticancer activity and low toxicity in vivo. In this study, the various gas-phase fragmentation routes were analyzed by electrospray ionization mass spectrometry (positive ion mode) in conjunction with tandem mass spectrometry (ESI-MS(n)) for the first time. In ESI-MS the fragment ion at m/z 289 (base peak) was formed by loss of the chlorine anion from the zwitterionic precursor SLXM-2. The fragment ion at m/z 232 was formed from the ion at m/z 289 by loss of 1-methylaziridine. The detailed gas-phase collision-induced dissociation (CID) fragmentation mechanisms obtained from the various precursor ions extracted from the zwitterionic SLXM-2 drug was obtained by tandem mass spectrometry analyses.

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confidence: 99%

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confidence: 99%

Gas‐fragmentation study of the novel synthetic zwitterionic drug 3‐methyl‐9‐(2‐oxa‐2λ5‐2H‐1,3,2‐oxazaphosphorine‐2‐cyclohexyl)‐3,6,9‐triazaspiro[5,5]undecane chloride (SLXM‐2) by electrospray ionization tandem mass spectrometry

Wang

Song

Wang

et al. 2010

Rapid Comm Mass Spectrometry

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Novel Class of Cyclophosphamide Prodrug: Cyclophosphamide Spiropiperaziniums (CPSP).

Sun

Guo

et al. 2006

ChemInform

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Organo-phosphorus compounds S 0080Novel Class of Cyclophosphamide Prodrug: Cyclophosphamide Spiropiperaziniums (CPSP). -Title compounds (III) (no yields given) are evaluated for in vivo anticancer activities against S180 and H22. The most potent derivatives (IIIb) and (IIIc) reveal a similar antitumor activity as cyclophosphamide (I). Furthermore, (IIIb) also exhibits much lower toxicity than (I). -(SUN, Q.; LI, R.-T.; GUO, W.; CUI*, J.-R.; CHENG, T.-M.; GE, Z.-M.; Bioorg.

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Synthesis, crystal structure, biological evaluation, electronic aspects of hydrogen bonds, and QSAR studies of some new N-(substituted phenylurea) diazaphosphore derivatives as anticancer agents

et al. 2016

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Novel class of cyclophosphamide prodrug: Cyclophosphamide spiropiperaziniums (CPSP)

Cited by 13 publications

References 22 publications

Gas‐fragmentation study of the novel synthetic zwitterionic drug 3‐methyl‐9‐(2‐oxa‐2λ5‐2H‐1,3,2‐oxazaphosphorine‐2‐cyclohexyl)‐3,6,9‐triazaspiro[5,5]undecane chloride (SLXM‐2) by electrospray ionization tandem mass spectrometry

Gas‐fragmentation study of the novel synthetic zwitterionic drug 3‐methyl‐9‐(2‐oxa‐2λ5‐2H‐1,3,2‐oxazaphosphorine‐2‐cyclohexyl)‐3,6,9‐triazaspiro[5,5]undecane chloride (SLXM‐2) by electrospray ionization tandem mass spectrometry

Novel Class of Cyclophosphamide Prodrug: Cyclophosphamide Spiropiperaziniums (CPSP).

Synthesis, crystal structure, biological evaluation, electronic aspects of hydrogen bonds, and QSAR studies of some new N-(substituted phenylurea) diazaphosphore derivatives as anticancer agents

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