131
Views
6
CrossRef citations to date
0
Altmetric
Reviews

Retiferols – synthesis and biological activity of a conceptually novel class of vitamin D analogs

, , &

Bibliography:

  • Mokrosz J. MM2 molecular modeling of retiferols. Unpublished work. 1993
  • Choliński J, Midland M, Kutner A, et al. Molecular modeling of disubstituted side-chain of vitamin D analogs. Polish J Chem 1995;69:229-34
  • Studzinski G, McLane J, Uskoković M. Signaling pathways for vitamin D-induced differentiation: implications for therapy of proliferative and neoplastic diseases. Crit Rev Eukar Gene 1993;3:279-312
  • Deeb KK, Trump DL, Johnson CS. Vitamin D signalling pathways in cancer: potential for anticancer therapeutics. Nat Rev Cancer 2007;7:684-700
  • Kang C. The biosynthesis of membrane lipids and steroids. Chapter 26. In: Berg JM, Tymoczko JL, Stryer L, editors, Biochemistry. 5th Edition. W H Freeman, New York; 2002
  • DeLuca HF. The metabolism, physiology, and function of vitamin D. In: Kumar R, editor, Vitamin D: basic and clinical aspects. Martinus Nijhoff Publishing, Boston; 1984. p. 1-68
  • Holick MF. Vitamin D: a millennium perspective. J Cell Biochem 2003;88:296-307
  • DeLuca HF, Yamamoto K, Takahashi J, et al. Stereoselective syntheses of (22R)-and (22S)-22-methyl-1alpha,25-dihydroxyvitamin D3: active vitamin D3 analogs with restricted side-chain conformation. J Org Chem 1993;58:2530-7
  • Deluca HF, Plum LA. Alterations in 1,25-dihydroxyvitamin D3 structure that produce profound changes in in-vivo activity. In: Feldman D, Pike JW, Adams JS, editors, Vitamin D. 3rd edition. Volume 2. Elsevier, London; 2011. p. 1429-35
  • Hartman DA, Basil JB, Robertson LW, et al. Microbial biotransformation of retinoic acid by cunninghamella echinulata and cunninghamella blakesleeana. Pharm Res 1990;7:270-3
  • Van Wauwe J, Coene MC, Cools W, et al. Liarozole fumarate inhibits the metabolism of 4-keto-all-trans-retinoic acid. Biochem Pharmacol 1994;47:737-41
  • Soprano DR, Teets BW, Soprano KJ. Role of retinoic acid in the differentiation of embryonal carcinoma and embryonic stem cells. In: Gerald L, editor, Vitamins & hormones. Volume 75. Elsevier, 2007. p. 69-95
  • Woollard G. Retinol, retinoic acid, carotenes and carotenoids: vitamin A structure and terminology. In: Preedy VR, editor, Vitamin A and carotenoids: chemisttry, analysis, function and effects. RSC Publishing, Cambridge; 2012
  • Laudrum JT. Carotenoids: physical, chemical and biological functions and properties. CRC Press, Boca Raton, FL; 2010
  • Dallavalle S, Zunino F. Synthetic retinoids as potential antitumour agents. Expert Opin Ther Patents 2005;15:1625-35
  • Alvarez R, Vaz B, Gronemeyer H, de Lera AR. Functions, therapeutic applications, and synthesis of retinoids and carotenoids. Chem Rev 2014;114:1-25
  • Sabbe K, D'Hallewyn C, De Clercq P, et al. Synthesis of CD-ring modified 1alpha,25-dihydroxy vitamin D analogues: E-ring analogues. Bioorg Med Chem Lett 1996;6:1697-702
  • Verstuyf A, Verlinden L, Van Baelen H, et al. The biological activity of nonsteroidal vitamin D hormone analogs lacking both the C- and D-rings. J Bone Min Res 1998;13:549-58
  • De Clercq P, Bouillon R, Vandewalle M. Novel structural analogues. of vitamin D. WO1995001960; 1995
  • Verlinden L, Eelen G, Bouillon R, et al. Analogs of calcitriol. In: Feldman D, Pike JW, Adams JS, editors, Vitamin D. 3rd edition. Volume 2. Elsevier, London; 2011. p. 1461-87
  • Stayrook KR, Carson MW, Ma YL, et al. Non-secosteroidal ligands and modulators. In: Feldman D, Pike JW, Adams JS, editors, Vitamin D. 3rd edition. Volume 2. Elsevier, London; 2011. p. 1497-508
  • Kutner A, Zhao H, Fitak H, et al. Synthesis of retiferol RAD1 and RAD2, the lead representatives of a new class of des-CD analogs of cholecalciferol. Bioorg Chem 1995;23:22-32
  • Chodynski M, Fitak H, Kutner A, et al. New pharmacotherapeutically active compounds. WO1995019963; 1995
  • Plonska-Ocypa K, Sicinski RR, DeLuca HF, et al. 13,13-Dimethyl-des-C,D analogues of (20S)-1alpha,25-dihydroxy-2-methylene-19-nor-vitamin D3 (2MD): total synthesis, docking to the VDR, and biological evaluation. Bioorg Med Chem 2011;19:7205-20
  • DeLuca H, Clagett-Dame M, Plum L, et al. 13,13-Dimethyl-des-C,D analogs of 1alpha,25-dihydroxy-19-nor-vitamin D3 compounds and topical composition dosage forms and methods of treating skin conditions thereof. WO2009094426; 2009
  • Barbier P, Bauer F, Mohr P, et al. Cyclohexanediol derivatives. US6184422; 2001
  • Hanazawa T, Wada T, Masuda T, et al. Novel synthetic approach to 19-nor-1alpha,25-dihydroxyvitamin D3 and its derivatives by suzuki-miyaura coupling in solution and on solid support. Org Lett 2001;3:3975-7
  • Hilpert H. Process for preparing retiferol derivatives. US6310262; 2001
  • Hilpert H, Wirz B. Novel versatile approach to an enantiopure 19-nor, des-C,D vitamin D3 derivative. Tetrahedron 2001;57:681-94
  • DeLuca HF, Plonska-Ocypa K, Sicinski RR, et al. Synthesis and biological evaluation of a des-C,D-analog of 2-methylene-19-nor-1alpha,25-(OH)2D3. J Steroid Biochem Mol Biol 2007;103:298-304
  • Saha U. Process for producing phosphine oxide vitamin D precursors. US8039676; 2011
  • Hilpert H, Wirz B. Enzymatic processes for producing intermediates useful in the manufacture of retiferol derivatives. US6403346; 2002
  • Wirz B, Iding H, Hilpert H. Multiselective enzymatic reactions for the synthesis of protected homochiral cis and trans-1,3,5-cyclohexanetriols. Tetrahedron: Asymm 2000;11:4171-8
  • Bauer F, Courtney LF. Cyclohexanediol derivatives. US5969190; 1999
  • Hanazawa T, Koyama A, Nakata K, et al. New convergent synthesis of 1alpha,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling between A-ring and C,D-ring parts. J Org Chem 2003;68:9767-72
  • Hanazawa T, Koyama A, Wada T, et al. Efficient convergent synthesis of 1alpha,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling. Org Lett 2003;5:523-5
  • Barbier P, Bauer FW, Mohr P, et al. Retiferol derivatives and their use in the treatment of skin diseases or conditions associated with photodamage. WO2002042247; 2002
  • Plonska-Ocypa K, Grzywacz P, Sicinski RR, et al. 13-Methyl-substituted des-C,D analogs of (20S)-1alpha,25-dihydroxy-2-methylene-19-nor-vitamin D3 (2MD): synthesis and biological evaluation. Bioorg Med Chem 2009;17:1747-63
  • DeLuca HF, Plonska Ocypa K, Sicinski R, et al. Des-C,D analogs of 1alpha,25-dihydroxy-19-nor-vitamin D3. WO2007028000; 2007
  • Fernandez S, Gotor-Fernandez V, Ferrero M, et al. Biocatalysis applied to the synthesis of vitamin D analogues. Curr Org Chem 2002;6:453-69
  • Bode SE, Wolberg M, Müller M. Stereoselective synthesis of 1,3-diols. Synthesis 2006;4:557-88
  • Bourguet W, Germain P, Gronemeyer H. Nuclear receptor ligand-binding domains: three-dimensional structures, molecular interactions and pharmacological implications. Trends Pharmacol Sci 2000;21:381-8
  • de Lera AR, Bourguet W, Altucci L, et al. Design of selective nuclear receptor modulators: RAR and RXR as a case study. Nat Rev Drug Discov 2007;6:811-20
  • Germain P, Chambon P, Eichele G, et al. International union of pharmacology. LX. Retinoic acid receptors. Pharmacol Rev 2006;58:712-25
  • Germain P, Chambon P, Eichele G, et al. International union of pharmacology. LXIII. Retinoid X receptors. Pharmacol Rev 2006;58:760-72
  • Huang P, Chandra V, Rastinejad F. Structural overview of the nuclear receptor superfamily: insights into physiology and therapeutics. Annu Rev Physiol 2010;72:247-72
  • Chee LC, Hendy J, Purton LE, McArthur GA. ATRA and the specific RARalpha agonist, NRX195183, have opposing effects on the clonogenicity of pre-leukemic murine AML1-ETO bone marrow cells. Leukemia 2013;6:1369-80
  • Esgleyes-Ribot T, Chandraratna RA, Lew-Kaya DA, et al. Response of psoriasis to a new topical retinoid, AGN 190168. J Am Acad Dermatol 1994;4:581-90
  • Wang Z, Chen Z. Acute promyelocytic leukemia: from highly fatal to highly curable. Blood 2008;111:2505-15
  • Hillestad L. Acute promyelocytic leukemia. Acta Med Scand 1957;159:189-94
  • De Thé H, Lavau C, Marchio A, et al. The PML-RAR alpha fusion mRNA generated by the t(15;17) translocation in acute promyelocytic leukemia encodes a functionally altered RAR. Cell 1991;66:675-84
  • Kastner P, Chan S. Function of RARalpha during the maturation of neutrophils. Oncogene 2001;20:7178-85
  • Breitman T, Selonick S, Collins S. Induction of differentiation of the human promyelocytic leukemia cell line (HL-60) by retinoic acid. Proc Natl Acad Sci USA 1980;77:2936-40
  • Nasr R, Guillemin M, Ferhi O, et al. Eradication of acute promyelocytic leukemia-initiating cells through PML-RARA degradation. Nat Med 2008;14:1333-42
  • Shen Y, Shen Z, Yan H, et al. Studies on the clinical efficacy and pharmacokinetics of low-dose arsenic trioxide in the treatment of relapsed acute promyelocytic leukemia: a comparison with conventional dosage. Leukemia 2001;15:735-41
  • Patatanian E, Thompson D. Retinoic acid syndrome: a review. J Clin Pharm Ther 2008;33:331-8
  • Petrie K, Zelent A, Waxman S. Differentiation therapy of acute myeloid leukemia: past, present and future. Curr Opin Hematol 2009;16:84-91
  • James S, Williams M, Newland A, et al. Leukemia cell differentiation: cellular and molecular interactions of retinoids and vitamin D. Gen Pharmacol 1999;32:143-54
  • Harrison J, Bershadskiy A. Clinical experience using vitamin D and analogs in the treatment of myelodysplasia and acute myeloid leukemia: a review of the literature. Leuk Res Treatment 2012;2012:125814
  • Gocek E, Kielbinski M, Kutner A, et al. Different susceptibilities to 1,25-dihydroxyvitamin D3-induced differentiation of AML cells carrying various mutations. Leuk Res 2010;34:649-57
  • Gocek E, Marchwicka A, Baurska H, et al. Opposite regulation of vitamin D receptor by ATRA in AML cells susceptible and resistant to vitamin D-induced differentiation. J Steroid Biochem Mol Biol 2012;132:220-6
  • Welsh J, Wietzke J, Zinser G, et al. Impact of the vitamin D3 receptor on growth-regulatory pathways in mammary gland and breast cancer. J Steroid Biochem Mol Biol 2002;83:85-92

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.