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Volumn 52, Issue 8, 2009, Pages 2204-2213

Synthesis and anti-inflammatory properties of 1 α,25-dihydroxy-16- ene-20-cyclopropyl-24-oxo-vitamin d 3, a hypocalcemic, stable metabolite of 1α,25-dihydroxy-16-ene-20-cyclopropylvitamin D 3

Author keywords

[No Author keywords available]

Indexed keywords

1ALPHA,25 DIHYDROXY 16 ENE 20 CYCLOPROPYL 24 OXOVITAMIN D3; 1ALPHA,25 DIHYDROXY 16 ENE 20 CYCLOPROPYLVITAMIN D3; ANTIINFLAMMATORY AGENT; CALCITRIOL; COLECALCIFEROL DERIVATIVE; DRUG METABOLITE; GAMMA INTERFERON; INTERLEUKIN 12; INTERLEUKIN 23; INTERLEUKIN 23P40; INTERLEUKIN 6; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; VITAMIN D RECEPTOR;

EID: 65249116273     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801365a     Document Type: Article
Times cited : (41)

References (40)
  • 1
    • 48749085956 scopus 로고    scopus 로고
    • Control of autoimmune diseases by the vitamin D endocrine system
    • Adorini, L.; Penna, G. Control of autoimmune diseases by the vitamin D endocrine system. Nat. Clin. Pract. Rheumatol. 2008, 4, 404-412.
    • (2008) Nat. Clin. Pract. Rheumatol , vol.4 , pp. 404-412
    • Adorini, L.1    Penna, G.2
  • 2
    • 22344444593 scopus 로고    scopus 로고
    • The nuclear receptor superfamily: A rosetta stone for physiology
    • Evans, R. M. The nuclear receptor superfamily: a rosetta stone for physiology. Mol. Endocrinol. 2005, 19, 1429-1438.
    • (2005) Mol. Endocrinol , vol.19 , pp. 1429-1438
    • Evans, R.M.1
  • 3
    • 0642367267 scopus 로고    scopus 로고
    • Current understanding of the function of the nuclear vitamin D receptor in response to its natural and synthetic ligands
    • Carlberg, C. Current understanding of the function of the nuclear vitamin D receptor in response to its natural and synthetic ligands. Recent. Resultss. Cancer. Res. 2003, 164, 29-42.
    • (2003) Recent. Resultss. Cancer. Res , vol.164 , pp. 29-42
    • Carlberg, C.1
  • 5
    • 33744826596 scopus 로고    scopus 로고
    • Cantorna, M. T. Vitamin D and its role in immunology: multiple sclerosis, and inflammatory bowel disease. Prog. Biophys. Mol. Biol. 2006, 92, 60-64.
    • Cantorna, M. T. Vitamin D and its role in immunology: multiple sclerosis, and inflammatory bowel disease. Prog. Biophys. Mol. Biol. 2006, 92, 60-64.
  • 6
    • 33749252164 scopus 로고    scopus 로고
    • The vitamin D receptor as a therapeutic target
    • Campbell, M. J.; Adorini, L. The vitamin D receptor as a therapeutic target. Expert Opin. Ther. Targets 2006, 10, 735-748.
    • (2006) Expert Opin. Ther. Targets , vol.10 , pp. 735-748
    • Campbell, M.J.1    Adorini, L.2
  • 7
    • 33845384182 scopus 로고    scopus 로고
    • Treatment of experimental autoimmune prostatitis in nonobese diabetic mice by the vitamin D receptor agonist elocalcitol
    • Penna, G.; Amuchastegui, S.; Cossetti, C; Aquilano, F.; Mariani, R.; Sanvito, F.; Doglioni, C; Adorini, L. Treatment of experimental autoimmune prostatitis in nonobese diabetic mice by the vitamin D receptor agonist elocalcitol. J. Immunol. 2006, 177, 8504-8511.
    • (2006) J. Immunol , vol.177 , pp. 8504-8511
    • Penna, G.1    Amuchastegui, S.2    Cossetti, C.3    Aquilano, F.4    Mariani, R.5    Sanvito, F.6    Doglioni, C.7    Adorini, L.8
  • 8
    • 0028988403 scopus 로고
    • Structure-function relationships in the vitamin D endocrine system
    • Bouillon, R; Okamura, W.; Norman, A. Structure-function relationships in the vitamin D endocrine system. Endocr. ReV. 1995, 16, 200- 257.
    • (1995) Endocr. ReV , vol.16 , pp. 200-257
    • Bouillon, R.1    Okamura, W.2    Norman, A.3
  • 9
    • 0036220629 scopus 로고    scopus 로고
    • The coming of age of 1, 25-dihydroxyvitamin D (3) analogs as immunomodulatory agents. Trends Mol
    • Mathieu, C.; Adorini, L. The coming of age of 1, 25-dihydroxyvitamin D (3) analogs as immunomodulatory agents. Trends Mol. M Ed. 2002, 8, 174-179.
    • (2002) M Ed , vol.8 , pp. 174-179
    • Mathieu, C.1    Adorini, L.2
  • 10
    • 23744437421 scopus 로고    scopus 로고
    • Noncalcemic actions of vitamin D receptor ligands
    • Nagpal, S.; Na, S.; Rathnachalam, R. Noncalcemic actions of vitamin D receptor ligands. Endocr. Rev. 2005, 26, 662-687.
    • (2005) Endocr. Rev , vol.26 , pp. 662-687
    • Nagpal, S.1    Na, S.2    Rathnachalam, R.3
  • 13
    • 29044445300 scopus 로고    scopus 로고
    • BXL628, a novel vitamin D3 analog arrests prostate growth in patients with benign prostatic hyperplasia: A randomized clinical trial
    • Colli, E.; Rigatti, P.; Montorsi, F.; Artibani, W.; Petta, S.; Mondaini, N.; Scarpa, R.; Usai, P.; Olivieri, L.; Maggi, M. BXL628, a novel vitamin D3 analog arrests prostate growth in patients with benign prostatic hyperplasia: a randomized clinical trial. Eur. Urol. 2006, 49, 82-86.
    • (2006) Eur. Urol , vol.49 , pp. 82-86
    • Colli, E.1    Rigatti, P.2    Montorsi, F.3    Artibani, W.4    Petta, S.5    Mondaini, N.6    Scarpa, R.7    Usai, P.8    Olivieri, L.9    Maggi, M.10
  • 15
    • 0028172166 scopus 로고    scopus 로고
    • Lemire, J. M.; Archer, D. C; Reddy, G. S. 1, 25-Dihydroxy-24-oxo- 16-ene-vitamin D3, a renal metabolite of the vitamin D analog 1, 25- dihydroxy-16-ene-vitamin D3, exerts immunosuppressive activity equal to its parent without causing hypercalcemia in vivo. Endocrinology 1994, 135, 2818-2821.
    • Lemire, J. M.; Archer, D. C; Reddy, G. S. 1, 25-Dihydroxy-24-oxo- 16-ene-vitamin D3, a renal metabolite of the vitamin D analog 1, 25- dihydroxy-16-ene-vitamin D3, exerts immunosuppressive activity equal to its parent without causing hypercalcemia in vivo. Endocrinology 1994, 135, 2818-2821.
  • 16
    • 0030332981 scopus 로고    scopus 로고
    • 1 R, 25-dihydroxy- 24-oxo-16-ene vitamin D3, a metabolite of a synthetic vitamin D3 analog, 1R, 25-dihydroxy-16-ene vitamin D3, is 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. 1 R, 25-dihydroxy- 24-oxo-16-ene vitamin D3, a metabolite of a synthetic vitamin D3 analog, 1R, 25-dihydroxy-16-ene vitamin D3, is equipotent to its parent in modulating growth and differentiation of human leukemic cells. J. Steraiid Biochem. MolRioL. 1996, 59, 405-412.
    • (1996) J. Steraiid Biochem. MolRioL , 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
  • 18
    • 0034900252 scopus 로고    scopus 로고
    • UMR 106 and ROS 17/2.8
    • (UMR 106 and ROS 17/2.8). J. Cell. Biochem 2001, 82, 599-609.
    • (2001) J. Cell. Biochem , vol.82 , pp. 599-609
  • 20
    • 0024786954 scopus 로고
    • Detection of three distinct patterns of T helper cell dysfunction in asymptomatic, human immunodeficiency virus-seropositive patients. Independence of CD4+ cell numbers and clinical staging
    • Clerici, M.; Stocks, N. I.; Zajac, R. A.; Boswell, R. N.; Lucey, D. R.; Via, C. S.; Shearer, G. M. Detection of three distinct patterns of T helper cell dysfunction in asymptomatic, human immunodeficiency virus-seropositive patients. Independence of CD4+ cell numbers and clinical staging. J. Clin. InVest. 1989, 84, 1892-1899.
    • (1989) J. Clin. InVest , vol.84 , pp. 1892-1899
    • Clerici, M.1    Stocks, N.I.2    Zajac, R.A.3    Boswell, R.N.4    Lucey, D.R.5    Via, C.S.6    Shearer, G.M.7
  • 21
    • 0030948854 scopus 로고    scopus 로고
    • Postrenal transplant MLR hypo-responders have fewer rejections and better graft survival than MLR hyper-responders
    • Kerman, R. H.; Susskind, B.; Katz, S. M.; Van Buren, C. T.; Kahan, B. D. Postrenal transplant MLR hypo-responders have fewer rejections and better graft survival than MLR hyper-responders. Transplant. Proc. 1997, 29, 1410-1411.
    • (1997) Transplant. Proc , vol.29 , pp. 1410-1411
    • Kerman, R.H.1    Susskind, B.2    Katz, S.M.3    Van Buren, C.T.4    Kahan, B.D.5
  • 22
    • 0027326050 scopus 로고
    • A novel immunosuppressant, IR-1116, which has a different biological mechanism from that of cyclosporine A
    • Matsumoto, S.; Marui, S.; Shiho, O.; Tsukamoto, K.; Yoshimura, N.; Oka, T. A novel immunosuppressant, IR-1116, which has a different biological mechanism from that of cyclosporine A. Eur. J. Immunol. 1993, 23, 2121-2128.
    • (1993) Eur. J. Immunol , vol.23 , pp. 2121-2128
    • Matsumoto, S.1    Marui, S.2    Shiho, O.3    Tsukamoto, K.4    Yoshimura, N.5    Oka, T.6
  • 23
    • 0031595992 scopus 로고    scopus 로고
    • Vitamin D3: A transcriptional modulator of the interferon- /gene
    • Cippitelli, M.; Santoni, A. Vitamin D3: a transcriptional modulator of the interferon- /gene. Eur. J. Immunol. 1998, 28, 3017-3030.
    • (1998) Eur. J. Immunol , vol.28 , pp. 3017-3030
    • Cippitelli, M.1    Santoni, A.2
  • 24
    • 0028288179 scopus 로고
    • Lymphokine production by human T cells in disease states
    • Romagnani, S. Lymphokine production by human T cells in disease states. Annu. ReV. Immunol. 1994, 12, 227-257.
    • (1994) Annu. ReV. Immunol , vol.12 , pp. 227-257
    • Romagnani, S.1
  • 25
    • 0029018309 scopus 로고
    • Immunosuppressive actions of 1, 25-dihydroxyvitamin D3: Preferential inhibition of Th1 functions
    • Lemire, J. M.; Archer, D. C..; Beck, L.; Spiegelberg, H. L. Immunosuppressive actions of 1, 25-dihydroxyvitamin D3: preferential inhibition of Th1 functions. J. Nutr 1995 125, 1704S-1708S.
    • (1995) J. Nutr , vol.125
    • Lemire, J.M.1    Archer, D.C.2    Beck, L.3    Spiegelberg, H.L.4
  • 26
    • 65249151130 scopus 로고    scopus 로고
    • Mattner, F.; Smiroldo, S.; Galbiati, F.; Muller, M.; Di Lucia, P.; Poliani, P. L.; Martino, G.; Panina-Bordignon, P.; Adorini, L. Inhibition of Th1 development and treatment of chronic-relapsing experimental allergic encephalomyelitis by a non-hypercalcemic analogue of 1, 25- dihydroxyvitamin D
    • Mattner, F.; Smiroldo, S.; Galbiati, F.; Muller, M.; Di Lucia, P.; Poliani, P. L.; Martino, G.; Panina-Bordignon, P.; Adorini, L. Inhibition of Th1 development and treatment of chronic-relapsing experimental allergic encephalomyelitis by a non-hypercalcemic analogue of 1, 25- dihydroxyvitamin D
  • 27
    • 0033975024 scopus 로고    scopus 로고
    • (3). Eur. J. Immunol. 2000, 30, 498-508.
    • (2000) Eur. J. Immunol , vol.30 , pp. 498-508
  • 28
    • 3142724031 scopus 로고    scopus 로고
    • Toll-like receptor signalling
    • Akira, S.; Takeda, K. Toll-like receptor signalling. Nat. ReV. Immunol. 2004 4, 499-511.
    • (2004) Nat. ReV. Immunol , vol.4 , pp. 499-511
    • Akira, S.1    Takeda, K.2
  • 29
    • 35349016235 scopus 로고    scopus 로고
    • Recognition of microorganisms and activation of the immune response
    • Medzhitov, R. Recognition of microorganisms and activation of the immune response. Nature 2007, 449, 819-826.
    • (2007) Nature , vol.449 , pp. 819-826
    • Medzhitov, R.1
  • 30
    • 38549102077 scopus 로고    scopus 로고
    • TNF-mediated inflammatory disease
    • Bradley, J. R. TNF-mediated inflammatory disease. J. Pathol. 2008, 214, 149-160.
    • (2008) J. Pathol , vol.214 , pp. 149-160
    • Bradley, J.R.1
  • 31
    • 20444489218 scopus 로고    scopus 로고
    • Design of effective immunotherapy for human autoimmunity
    • Feldmann, M.; Steinman, L. Design of effective immunotherapy for human autoimmunity. Nature 2005, 435, 612-619.
    • (2005) Nature , vol.435 , pp. 612-619
    • Feldmann, M.1    Steinman, L.2
  • 34
    • 45749101727 scopus 로고    scopus 로고
    • Induction and effector functions of T (H) 17 cells
    • Bettelli, E.; Korn, T.; Oukka, M.; Kuchroo, V. K. Induction and effector functions of T (H) 17 cells. Nature 2008, 453, 1051-1057.
    • (2008) Nature , vol.453 , pp. 1051-1057
    • Bettelli, E.1    Korn, T.2    Oukka, M.3    Kuchroo, V.K.4
  • 35
    • 84884872452 scopus 로고    scopus 로고
    • Vitamin D metabolism
    • Feldman, D, Glorieux, F. H, Pike, J. W, Eds, Academic Press, Inc, New York
    • Horst, R. L.; Reinhardt, T. A.; Reddy, G. S. Vitamin D metabolism. In Vitamin D: Feldman, D., Glorieux, F. H., Pike, J. W., Eds.; Academic Press, Inc.: New York, 2005; pp 15-35.
    • (2005) Vitamin D , pp. 15-35
    • Horst, R.L.1    Reinhardt, T.A.2    Reddy, G.S.3
  • 36
    • 84884898751 scopus 로고    scopus 로고
    • The 25-Hydroxyvitamin D 24-Hydroxylase
    • Feldman, D, Glorieux, F. H, Pike, J. W, Eds, Academic Press: New York
    • Omdahl, J. L.; May, B. The 25-Hydroxyvitamin D 24-Hydroxylase. In Vitamin D; Feldman, D., Glorieux, F. H., Pike, J. W., Eds.; Academic Press: New York, 2005; pp 85-104.
    • (2005) Vitamin D , pp. 85-104
    • Omdahl, J.L.1    May, B.2
  • 37
    • 4344665018 scopus 로고    scopus 로고
    • Wang, T. T.; Nestel, F. P.; Bourdeau, V.; Nagai, Y.; Wang, Q.; Liao, J.; Tavera-Mendoza, L.; Lin, R.; Hanrahan, J. W.; Mader, S.; White, J. H. Cutting edge: 1, 25-dihydroxyvitamin D3 is a direct inducer of antimicrobial peptide gene expression. J Ammung. 2004, 173, 2909- 2912.
    • Wang, T. T.; Nestel, F. P.; Bourdeau, V.; Nagai, Y.; Wang, Q.; Liao, J.; Tavera-Mendoza, L.; Lin, R.; Hanrahan, J. W.; Mader, S.; White, J. H. Cutting edge: 1, 25-dihydroxyvitamin D3 is a direct inducer of antimicrobial peptide gene expression. J Ammung. 2004, 173, 2909- 2912.
  • 40
    • 65249118690 scopus 로고    scopus 로고
    • Uskokovic, M. R.; Marczak, S.; Jankowski, P.; Adorini, L. Deuteroalkyl vitamin D3 compounds and their pharmaceutical compositions. WO200738250, 2007.
    • Uskokovic, M. R.; Marczak, S.; Jankowski, P.; Adorini, L. Deuteroalkyl vitamin D3 compounds and their pharmaceutical compositions. WO200738250, 2007.


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