2009
DOI: 10.1021/jm900780q
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Calcitriol Derivatives with Two Different Side Chains at C-20. V. Potent Inhibitors of Mammary Carcinogenesis and Inducers of Leukemia Differentiation

Abstract: Calcitriol is implicated in many cellular functions including cellular growth and differentiation thus explaining its anti-tumor effects. It was shown that gemini, the calcitriol derivative containing two side chain at C20, is also active in gene transcription with enhanced anti-tumor activity. We have now further optimized both the A-ring and the two side chains. The chemical structures of the resulting 18 geminis were correlated with biological activities. Those containing the 1α-fluoro Aring are the least a… Show more

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Cited by 33 publications
(34 citation statements)
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“…1α,25(OH) 2 D 3 and a Gemini vitamin D analog (BXL0124; 1α25-dihydroxy-20R-21(3-hydroxy-3-deuteromethyl-4,4,4-trideuterobutyl)-23-yne-26,27-hexafluorocholecalciferol, >95% purity) were provided by BioXell, Inc. (Nutley, NJ) (17). SUM159 breast cancer cells were obtained from Asterand (Detroit, MI).…”
Section: Methodsmentioning
confidence: 99%
“…1α,25(OH) 2 D 3 and a Gemini vitamin D analog (BXL0124; 1α25-dihydroxy-20R-21(3-hydroxy-3-deuteromethyl-4,4,4-trideuterobutyl)-23-yne-26,27-hexafluorocholecalciferol, >95% purity) were provided by BioXell, Inc. (Nutley, NJ) (17). SUM159 breast cancer cells were obtained from Asterand (Detroit, MI).…”
Section: Methodsmentioning
confidence: 99%
“…1␣,25(OH) 2 D 3 and Gemini vitamin D analog 1␣,25-dihydroxy-20R-21(3-hydroxy-3-deuteromethyl-4,4,4-trideuterobutyl)-23-yne-26,27-hexafluoro-cholecalciferol (BXL0124;Maehr et al, 2009; Ͼ95% purity) (Fig. 1A) were provided by BioXell, Inc. (Nutley, NJ) and dissolved in dimethyl sulfoxide (DMSO).…”
Section: Methodsmentioning
confidence: 99%
“…Calcitriol was purchased from Sigma, and all gemini compounds (>95% purity) (Figure 1) were prepared as described (Maehr et al 2009). All compounds were used in ethanol solutions.…”
Section: Methodsmentioning
confidence: 99%
“…Both compounds are closely related to cholecalciferol wherein the side chain of cholecalciferol was modified by a 23-triple bond and the six hydrogen atoms at positions 26 and 27 were replaced with fluorine atoms, and the position 21 was extended with a (3-hydroxy-3-trideuteromethyl-4,4,4-trideuterobutyl) group, thus maintaining the 20(R) configuration of cholecalciferol (Maehr et al 2009). These chemical alterations were selected to prevent or retard biological degradation initiated by 24-hydroxylation thus extending the half-life of the compound.…”
Section: Introductionmentioning
confidence: 99%