Citation: Hu Daihua, Chen Wang. Advances in Syntheses and Biological Activities of Vitamin D₂ Analogues[J]. Chemistry, ;2017, 80(8): 715-724. shu

Advances in Syntheses and Biological Activities of Vitamin D₂ Analogues

Hu Daihua ,
Chen Wang

Vitamin D Research Institute, Shaanxi Sci-Tech University, Hanzhong 723000

Received Date: 19 December 2016
Accepted Date: 8 April 2017

Figures(1)

1α, 25-Dihydroxyvitamin D₂(1α, 25-(OH)₂-D₂; 125D2) is the active metabolite form of vitamin D₂, and 1α, 25-dihydroxyvitamin D₃(1α, 25-(OH)₂-D₃; 125D) is the most active metabolite of vitamin D₃. The biological activity of 125D2 and 125D is similar, but the therapeutic application of 125D is limited by induction of hypercalcemia. Vitamin D₂ and analogues are thought to be generally less toxic than the respective vitamin D₃ compounds. This article reviews the recent development of two 125D2 analogues (doxercalciferol and paricalcitol) showed good clinical effect in organic syntheses, and new research in the design and syntheses of the structural modifications in the side chain, 19-nor, C3-substituted in A ring, and nonadeuterated isotope labeling 125D2 analogues, and the relation between the structure and the biological activities, aimed at guiding significance to the syntheses and clinical development of new selective biological vitamin D₂ analogues.
- 1α, 25-dihydroxyvitamin D₂,
- Analogues,
- Doxercalciferol,
- Paricalcitol,
- Synthesis,
- Biological activities
1. [1]
  G Jones, H K Schnoes, H F De Luca. Biochemistry, 1975, 14(6):1250~1256.
2. [2]
  H F DeLuca, L A Plum, M Clagett-Dame. J. Steroid. Biochem., 2007, 103(3):263~268.
3. [3]
  N Urushino, K Yasuda, S Ikushiro et al. Biochem. Biophys. Res. Commun., 2009, 384(2):144~148.
4. [4]
  G Jones, L A Baxter, H F De Luca et al. Biochemistry, 1976, 15(3):713~716.
5. [5]
6. [6]
  M Chodyński, J Wietrzyk, E Marcinkowska et al. Steroids, 2002, 67(9):789~798.
7. [7]
  Y Tachibana. Bull. Chem. Soc. Jpn., 1988, 61(11):3915~3918.
8. [8]
9. [9]
  B G Anderson, W E Bauta, Jr W R Cantrell. Org. Proc. Res. Dev., 2012, 16(5):967~975.
10. [10]
11. [11]
  Y Ji, X Wang, R J Donnelly et al. J. Cell. Physiol., 2002, 191(2):198~207.
12. [12]
  B Filip, M Milczarek, J Wietrzyk et al. J. Steroid. Biochem., 2010, 121(1):399~402.
13. [13]
  S Nadkarni, M Chodynski, K Krajewski et al. J. Steroid. Biochem., 2016, 164:45~49.
14. [14]
  A Piotrowska, J Wierzbicka, S Nadkarni et al. Int. J. Mol. Sci., 2016, 17(1):76.
15. [15]
  M Chodyński, J Wietrzyk, E Marcinkowska et al. Steroids, 2002, 67(9):789~798.
16. [16]
  J Wietrzyk, D Nevozhay, M Milczarek et al. Cancer. Chemoth. Pharm., 2008, 62(5):787~797.
17. [17]
  H Baurska, A Klopot, M Kielbinski et al. J. Steroid. Biochem., 2011, 126(1):46~54.
18. [18]
  N R Bolla, A Corcoran, K Yasuda et al. J. Steroid. Biochem., 2016, 164:50~55.
19. [19]
  Z Gándara, M Pérez, X Pérez-García et al. Tetrahed. Lett., 2009, 50(34):4874~4877.
20. [20]
  Z Gándara, M Pérez, D G Salomón et al. Bioorg. Med. Chem. Lett., 2012, 22(19):6276~6279.
21. [21]
  S Vinhas, S Vázquez, J E Rodríguez-Borges et al. J. Steroid. Biochem., 2016
22. [22]
23. [23]
24. [24]
  L Li, L Yue, J Xue et al. Chin. Sci. Bull., 2012, 57(14):1616~1619.
25. [25]
  A Toyoda, H Nagai, T Yamada et al. Tetrahedron, 2009, 65(48):10002~10008.
26. [26]
  R Samala, S Sharma, M K Basu et al. Tetrahed. Lett., 2016, 57(12):1309~1312.
27. [27]
  A Pietraszek, M Malińska, M Chodyński et al. Steroids, 2013, 78(10):1003~1014.
28. [28]
  M Nachliely, E Sharony, A Kutner et al. J. Steroid. Biochem., 2016, 164:59~65.
29. [29]
  J Grote, S Gayda. Tetrahed. Lett., 2014, 55(43):5955~5959.
30. [30]
  R Sigüeiro, R Otero, P González-Berdullas et al. J. Steroid. Biochem., 2015, 148:31~33.
31. [31]
32. [32]
  R Bouillon, W H Okamura, A W Norman. Endocr. Rev., 1995, 16(2):200~257.
33. [33]
  R Sigüeiro, A Álvarez, R Otero et al. J. Steroid. Biochem., 2014, 144:204~206.
1. [1]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
2. [2]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
3. [3]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
4. [4]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
5. [5]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
6. [6]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
7. [7]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
8. [8]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
9. [9]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
10. [10]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
11. [11]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
12. [12]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
13. [13]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
14. [14]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
15. [15]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
16. [16]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
17. [17]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
18. [18]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
19. [19]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
20. [20]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(2913)
HTML views(314)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Advances in Syntheses and Biological Activities of Vitamin D2 Analogues

Metrics

通讯作者: 陈斌, bchen63@163.com

Advances in Syntheses and Biological Activities of Vitamin D₂ Analogues