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Volumn 71, Issue 3-4, 1999, Pages 111-121

Enhanced biological activity of 1α,25-dihydroxy-20-epi-vitamin D3, the C-20 epimer of 1α,25-dihydroxyvitamin D3, is in part due to its metabolism into stable intermediary metabolites with significant biological activity

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL; COLECALCIFEROL;

EID: 0033406692     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-0760(99)00130-2     Document Type: Article
Times cited : (29)

References (26)
  • 1
    • 0028988403 scopus 로고
    • Structure-function relationships in the vitamin D endocrine system
    • Bouillon R., Okamura W.H., Norman A.W. Structure-function relationships in the vitamin D endocrine system. Endocr. Rev. 16:1995;200-257.
    • (1995) Endocr. Rev. , vol.16 , pp. 200-257
    • Bouillon, R.1    Okamura, W.H.2    Norman, A.W.3
  • 3
    • 0027485704 scopus 로고
    • Metabolism of 1α,25(OH)2-16-ene-D3 in kidney: Influence of structural modification of D-ring on side chain metabolism
    • Reddy G.S., Clark J.W., Tserng K.-Y., Uskokovic M.R., McLane J.A. Metabolism of 1α,25(OH)2-16-ene-D3 in kidney: Influence of structural modification of D-ring on side chain metabolism. Bioorg. Med. Chem. Lett. 3:1993;1879-1884.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 1879-1884
    • Reddy, G.S.1    Clark, J.W.2    Tserng, K.-Y.3    Uskokovic, M.R.4    McLane, J.A.5
  • 4
    • 0028172166 scopus 로고
    • 1α,25-dihydroxy-24oxo-16ene-vitamin D3, a renal metabolite of the vitamin D analog 1α,25-dihydroxy-16ene-vitamin D3, exerts immunosuppressive activity equal to its parent without causing hypercalcemia in vivo
    • Lemire J.M., Archer D.C., Reddy G.S. 1α,25-dihydroxy-24oxo-16ene-vitamin D3, a renal metabolite of the vitamin D analog 1α,25-dihydroxy-16ene-vitamin D3, exerts immunosuppressive activity equal to its parent without causing hypercalcemia in vivo. Endocrinology. 135:1994;2818-2821.
    • (1994) Endocrinology , vol.135 , pp. 2818-2821
    • Lemire, J.M.1    Archer, D.C.2    Reddy, G.S.3
  • 5
    • 0030332981 scopus 로고    scopus 로고
    • 1α,25-dihydroxy-24-oxo-16-ene vitamin D3, a metabolite of a synthetic vitamin D3 analog, 1α,25-dihydroxy-16-ene vitamin D3, is equipotent to its parent in modulating equipotent to its parent in modulating growth and differentiation of human leukemic cells
    • Siu-Caldera M.-L., Clark J.W., Santos-Moore A., Peleg S., Liu Y.-Y., Uskokovic M.R., Sharma S., Reddy G.S. 1α,25-dihydroxy-24-oxo-16-ene vitamin D3, a metabolite of a synthetic vitamin D3 analog, 1α,25-dihydroxy-16-ene vitamin D3, is equipotent to its parent in modulating equipotent to its parent in modulating growth and differentiation of human leukemic cells. J. Steroid Biochem. Molec. Biol. 59:1996;405-412.
    • (1996) J. Steroid Biochem. Molec. Biol. , vol.59 , pp. 405-412
    • Siu-Caldera, M.-L.1    Clark, J.W.2    Santos-Moore, A.3    Peleg, S.4    Liu, Y.-Y.5    Uskokovic, M.R.6    Sharma, S.7    Reddy, G.S.8
  • 6
    • 0025866899 scopus 로고
    • 20-epi-vitamin D3 analogues: A novel class of potent regulators of cell growth and immune responses
    • Binderup L., Latini S., Binderup E., Bretting C., Calverley M., Hansen K. 20-epi-vitamin D3 analogues: A novel class of potent regulators of cell growth and immune responses. Biochem. Pharmacol. 42:1991;1569-1575.
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 1569-1575
    • Binderup, L.1    Latini, S.2    Binderup, E.3    Bretting, C.4    Calverley, M.5    Hansen, K.6
  • 8
    • 0029959504 scopus 로고    scopus 로고
    • 20-epi-vitamin D3 analogs. Potent modulators of proliferation and differentiation of breast cancer cell lines in vitro
    • Elstner E., Heber D., Koeffler H.P. 20-epi-vitamin D3 analogs. Potent modulators of proliferation and differentiation of breast cancer cell lines in vitro. Adv. Exp. Med. Biol. 399:1996;53-70.
    • (1996) Adv. Exp. Med. Biol. , vol.399 , pp. 53-70
    • Elstner, E.1    Heber, D.2    Koeffler, H.P.3
  • 9
    • 0030902662 scopus 로고    scopus 로고
    • Effects of 1α,25-dihydroxyvitamin D3 and its 20-epi analogues (MC 1288, MC 1301, KH 1060), on clonal keratinocyte growth: Evidence for differentiation of keratinocyte stem cells and analysis of the modulatory effects of cytokines
    • Gniadecki R. Effects of 1α,25-dihydroxyvitamin D3 and its 20-epi analogues (MC 1288, MC 1301, KH 1060), on clonal keratinocyte growth: evidence for differentiation of keratinocyte stem cells and analysis of the modulatory effects of cytokines. Br. J. Pharmacol. 120:1997;1119-1127.
    • (1997) Br. J. Pharmacol. , vol.120 , pp. 1119-1127
    • Gniadecki, R.1
  • 10
    • 0028218712 scopus 로고
    • Increased biological activity of 20-epi-1,25-dihydroxyvitamin D3 is due to reduced catabolism and altered protein binding
    • Dilworth F.J., Calverley M.J., Makin H.L.J., Jones G. Increased biological activity of 20-epi-1,25-dihydroxyvitamin D3 is due to reduced catabolism and altered protein binding. Biochem. Pharmacol. 47:1994;987-993.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 987-993
    • Dilworth, F.J.1    Calverley, M.J.2    Makin, H.L.J.3    Jones, G.4
  • 11
    • 0028960317 scopus 로고
    • Pharmacokinetic studies of vitamin D analogues: Relationship to vitamin D binding protein (DBP)
    • Kissmeyer A.-M., Mathiasen I.S., Latini S., Binderup L. Pharmacokinetic studies of vitamin D analogues: relationship to vitamin D binding protein (DBP). Endocrine. 3:1995;263-266.
    • (1995) Endocrine , vol.3 , pp. 263-266
    • Kissmeyer, A.-M.1    Mathiasen, I.S.2    Latini, S.3    Binderup, L.4
  • 12
    • 0028917557 scopus 로고
    • Distinct conformational changes induced by 20-epi analogues of 1α,25-dihydroxyvitamin D3 are associated with enhanced activation of the vitamin D receptor
    • Peleg S., Sastry M., Collins E.D., Bishop J.E., Norman A.W. Distinct conformational changes induced by 20-epi analogues of 1α,25-dihydroxyvitamin D3 are associated with enhanced activation of the vitamin D receptor. J. Biol. Chem. 270:1995;10551-10558.
    • (1995) J. Biol. Chem. , vol.270 , pp. 10551-10558
    • Peleg, S.1    Sastry, M.2    Collins, E.D.3    Bishop, J.E.4    Norman, A.W.5
  • 13
    • 0029741914 scopus 로고    scopus 로고
    • High-affinity nuclear receptor binding of 20-epi analogues of 1,25-dihydroxyvitamin D3 correlates well with gene activation
    • Nayeri S., Mathiasen I.S., Binderup L., Carlberg C. High-affinity nuclear receptor binding of 20-epi analogues of 1,25-dihydroxyvitamin D3 correlates well with gene activation. J. Cell. Biochem. 62:1996;325-333.
    • (1996) J. Cell. Biochem. , vol.62 , pp. 325-333
    • Nayeri, S.1    Mathiasen, I.S.2    Binderup, L.3    Carlberg, C.4
  • 14
    • 0029773872 scopus 로고    scopus 로고
    • Conformational change and enhanced stabilization of the vitamin D receptor by the 1α-,25-dihydroxyvitamin D3 analog KH1060
    • van den Bemd G.C.M., Pols H.A.P., Birkenhager J.C., van Leeuwen J.P.T.M. Conformational change and enhanced stabilization of the vitamin D receptor by the 1α-,25-dihydroxyvitamin D3 analog KH1060. Proc. Natl. Acad. Sci. USA. 93:1996;10685-10690.
    • (1996) Proc. Natl. Acad. Sci. USA , vol.93 , pp. 10685-10690
    • Van Den Bemd, G.C.M.1    Pols, H.A.P.2    Birkenhager, J.C.3    Van Leeuwen, J.P.T.M.4
  • 15
    • 0030614448 scopus 로고    scopus 로고
    • Differential interaction of 1α,25-dihydroxyvitamin D3 analogues and their 20-epi homologues with the vitamin D receptor
    • Liu Y.-Y., Collins E.D., Norman A.W., Peleg S. Differential interaction of 1α,25-dihydroxyvitamin D3 analogues and their 20-epi homologues with the vitamin D receptor. J. Biol. Chem. 272:1997;3336-3345.
    • (1997) J. Biol. Chem. , vol.272 , pp. 3336-3345
    • Liu, Y.-Y.1    Collins, E.D.2    Norman, A.W.3    Peleg, S.4
  • 16
    • 0020201869 scopus 로고
    • Inhibition of 25-hydroxyvitamin D3-1-hydroxylase by chronic metabolic acidosis
    • Reddy G.S., Jones G., Kooh S.W., Fraser D. Inhibition of 25-hydroxyvitamin D3-1-hydroxylase by chronic metabolic acidosis. Am. J. Physiol. 243:1982;E265-E271.
    • (1982) Am. J. Physiol. , vol.243
    • Reddy, G.S.1    Jones, G.2    Kooh, S.W.3    Fraser, D.4
  • 17
    • 0023109720 scopus 로고
    • Isolation and identification of 1,23-dihydroxy-24,25,26,27-tetranorvitamin D3, a new metabolite of 1,25-dihydroxyvitamin D3 produced in rat kidney
    • Reddy G.S., Tserng K.-Y., Thomas B.R., Dayal R., Norman A.W. Isolation and identification of 1,23-dihydroxy-24,25,26,27-tetranorvitamin D3, a new metabolite of 1,25-dihydroxyvitamin D3 produced in rat kidney. Biochemistry. 26:1987;324-331.
    • (1987) Biochemistry , vol.26 , pp. 324-331
    • Reddy, G.S.1    Tserng, K.-Y.2    Thomas, B.R.3    Dayal, R.4    Norman, A.W.5
  • 18
    • 0032230321 scopus 로고    scopus 로고
    • Differential use of transcription activation function 2 domain of the vitamin D receptor by 1,25-dihydroxyvitamin D3 and its A ring-modified analogs
    • Peleg S., Nguyen C., Woodard B.T., Lee J.K., Posner G.H. Differential use of transcription activation function 2 domain of the vitamin D receptor by 1,25-dihydroxyvitamin D3 and its A ring-modified analogs. Mol. Endocrinol. 12:1998;525-535.
    • (1998) Mol. Endocrinol. , vol.12 , pp. 525-535
    • Peleg, S.1    Nguyen, C.2    Woodard, B.T.3    Lee, J.K.4    Posner, G.H.5
  • 19
    • 0025678705 scopus 로고
    • The vitamin D-responsive element in the human osteocalcin gene: Association with a nuclear proto-oncogene enhancer
    • Ozono K., Liao S.A., Kerner S.A., Scott R.A., Pike J.W. The vitamin D-responsive element in the human osteocalcin gene: association with a nuclear proto-oncogene enhancer. J. Biol. Chem. 265:1990;21881-21888.
    • (1990) J. Biol. Chem. , vol.265 , pp. 21881-21888
    • Ozono, K.1    Liao, S.A.2    Kerner, S.A.3    Scott, R.A.4    Pike, J.W.5
  • 20
    • 0021770787 scopus 로고
    • High level transient expression of a chloramphenicol acetyl transferase gene by DEAE-dextran mediated DNA transfection coupled with a dimethyl sulfoxide or glycerol shock treatment
    • Lopata M.A., Cleveland D.W., Sollner-Webb B. High level transient expression of a chloramphenicol acetyl transferase gene by DEAE-dextran mediated DNA transfection coupled with a dimethyl sulfoxide or glycerol shock treatment. Nucleic Acids Res. 12:1984;5707-5717.
    • (1984) Nucleic Acids Res. , vol.12 , pp. 5707-5717
    • Lopata, M.A.1    Cleveland, D.W.2    Sollner-Webb, B.3
  • 21
    • 0028982708 scopus 로고
    • Human osteoblasts in culture metabolize both 1α,25-dihydroxyvitamin D3 and its precursor 25-hydroxyvitamin D3 into their respective lactones
    • Siu-Caldera M.-L., Zou L., Ehrlich M.G., Schwartz E.R., Ishizuka S., Reddy G.S. Human osteoblasts in culture metabolize both 1α,25-dihydroxyvitamin D3 and its precursor 25-hydroxyvitamin D3 into their respective lactones. Endocrinology. 136:1995;4195-4203.
    • (1995) Endocrinology , vol.136 , pp. 4195-4203
    • Siu-Caldera, M.-L.1    Zou, L.2    Ehrlich, M.G.3    Schwartz, E.R.4    Ishizuka, S.5    Reddy, G.S.6
  • 22
    • 0030611005 scopus 로고    scopus 로고
    • Vitamin D3 analogs and their 24-oxo metabolites equally inhibit clonal proliferation of a variety of cancer cells but have differing molecular effects
    • Campbell M.J., Reddy G.S., Koeffler H.P. Vitamin D3 analogs and their 24-oxo metabolites equally inhibit clonal proliferation of a variety of cancer cells but have differing molecular effects. J. Cell. Biochem. 66:1997;413-425.
    • (1997) J. Cell. Biochem. , vol.66 , pp. 413-425
    • Campbell, M.J.1    Reddy, G.S.2    Koeffler, H.P.3
  • 24
    • 0026512664 scopus 로고
    • Effects of vitamin D-binding proteins on HL-60 cell differentiation induced by 26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D3
    • Honda A., Nakashima N., Mori Y., Katsumata T., Ishizuka S. Effects of vitamin D-binding proteins on HL-60 cell differentiation induced by 26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D3. J. Steroid Biochem. Molec. Biol. 41:1992;109-112.
    • (1992) J. Steroid Biochem. Molec. Biol. , vol.41 , pp. 109-112
    • Honda, A.1    Nakashima, N.2    Mori, Y.3    Katsumata, T.4    Ishizuka, S.5
  • 25
    • 0028144051 scopus 로고
    • Differences in metabolism between 26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3 in cultured neonatal mouse calvaria
    • Harada M., Miyahara T., Kajita-Kondo S., Kozakai A., Higuchi S., Otomo S., Kozuka H. Differences in metabolism between 26,26,26,27,27,27-hexafluoro-1α,25-dihydroxyvitamin D3 and 1α,25-dihydroxyvitamin D3 in cultured neonatal mouse calvaria. Res. Commun. Molec. Pathol. Pharma. 86:1994;183-193.
    • (1994) Res. Commun. Molec. Pathol. Pharma. , vol.86 , pp. 183-193
    • Harada, M.1    Miyahara, T.2    Kajita-Kondo, S.3    Kozakai, A.4    Higuchi, S.5    Otomo, S.6    Kozuka, H.7
  • 26
    • 0030698176 scopus 로고    scopus 로고
    • The vitamin D analog, KH1060, is rapidly degraded both in vivo and in vitro via several pathways: Principal metabolites generated retain significant biological activity
    • Dilworth F.J., Williams G.R., Kissmeyer A.-M., Nielsen J.L., Binderup E., Calverley M.J., Makin H.L.J., Jones G. The vitamin D analog, KH1060, is rapidly degraded both in vivo and in vitro via several pathways: principal metabolites generated retain significant biological activity. Endocrinology. 138:1997;5485-5496.
    • (1997) Endocrinology , vol.138 , pp. 5485-5496
    • Dilworth, F.J.1    Williams, G.R.2    Kissmeyer, A.-M.3    Nielsen, J.L.4    Binderup, E.5    Calverley, M.J.6    Makin, H.L.J.7    Jones, G.8


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