Gemini Analogs of Vitamin D

被引：5
|
作者：
Pazos, Gonzalo [1 ]
Rivadulla, Marcos L. [1 ]
Perez-Garcia, Xenxo [1 ]
Gandara, Zoila [1 ,2 ]
Perez, Manuel [1 ,3 ]
机构：
[1] Univ Vigo, Fac Quim, Dept Quim Organ, Vigo 36202, Spain
[2] Palacky Univ, Fac Sci, Dept Chem Biol & Genet, Ctr Reg Hana Biotechnol & Agr Res, CZ-78371 Olomouc, Czech Republic
[3] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
CURRENT TOPICS IN MEDICINAL CHEMISTRY | 2014年 / 14卷 / 21期
关键词：
Chemical synthesis; Gemini analogs; Steroid; Vitamin D; LIGAND-BINDING DOMAIN; DIFFERENT SIDE-CHAINS; NUCLEAR RECEPTOR; CALCITRIOL DERIVATIVES; MAMMARY TUMORIGENESIS; EXPRESSION; D-3;
D O I：
10.2174/1568026615666141208100411
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The Gemini analogs are the last significant contribution to the family of vitamin D derivatives in medicine, for the treatment of cancer. The first Gemini analog was characterized by two symmetric side chains at C-20. Following numerous modifications, the most active analog bears a C-23-triple bond, C-26, 27-hexafluoro substituents on one side chain and a terminal trideuteromethylhydroxy group on the other side chain. This progression was possible due to improvements in the synthetic methods for the preparation of these derivatives, which allowed for increasing molecular complexity and complete diastereoselective control at C-20 and the substituted sidechains.
引用
收藏
页码：2388 / 2397
页数：10
相关论文
共 50 条
  • [21] Vitamin D analogs in cancer prevention and therapy
    Reichrath, Joerg
    Tilgen, Wolfgang
    Diedrich, Klaus
    Friedrich, Michael
    ANTICANCER RESEARCH, 2006, 26 (4A) : 2511 - 2514
  • [22] Inhibition of the Transition of Ductal Carcinoma In Situ to Invasive Ductal Carcinoma by a Gemini Vitamin D Analog
    Wahler, Joseph
    So, Jae Young
    Kim, Yeoun Chan
    Liu, Fang
    Maehr, Hubert
    Uskokovic, Milan
    Suh, Nanjoo
    CANCER PREVENTION RESEARCH, 2014, 7 (06) : 617 - 626
  • [23] Regulation of the vitamin D receptor by vitamin D lactam derivatives
    Asano, Lisa
    Waku, Tsuyoshi
    Abe, Rumi
    Kuwabara, Naoyuki
    Ito, Ichiaki
    Yanagisawa, Junn
    Nagasawa, Kazuo
    Shimizu, Toshiyuki
    FEBS LETTERS, 2016, 590 (18) : 3270 - 3279
  • [24] Vitamin D Analogs Regulate the Vitamin D System and Cell Viability in Ovarian Cancer Cells
    Piatek, Karina
    Kutner, Andrzej
    Cacsire Castillo-Tong, Dan
    Manhardt, Teresa
    Kupper, Nadja
    Nowak, Urszula
    Chodynski, Michal
    Marcinkowska, Ewa
    Kallay, Enikoe
    Schepelmann, Martin
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (01)
  • [25] Altered Vitamin D receptor-coactivator interactions reflect superagonism of Vitamin D analogs
    Eelen, G
    Verlinden, L
    Van Camp, M
    Claessens, F
    De Clercq, P
    Vandewalle, M
    Bouillon, R
    Verstuyf, A
    JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2005, 97 (1-2): : 65 - 68
  • [26] New vitamin D analogs as potential therapeutics in melanoma
    Szyszka, Paulina
    Zmijewski, Michal A.
    Slominski, Andrzej T.
    EXPERT REVIEW OF ANTICANCER THERAPY, 2012, 12 (05) : 585 - 599
  • [27] Vitamin D analogs: Therapeutic applications and mechanisms for selectivity
    Brown, Alex J.
    Slatopolsky, Eduardo
    MOLECULAR ASPECTS OF MEDICINE, 2008, 29 (06) : 433 - 452
  • [28] Rationale for active vitamin D and analogs in the treatment of osteoporosis
    Nishii, Y
    JOURNAL OF CELLULAR BIOCHEMISTRY, 2003, 88 (02) : 381 - 386
  • [29] The Roles of Vitamin D and Its Analogs in Inflammatory Diseases
    Lin, Zongtao
    Li, Wei
    CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) : 1242 - 1261
  • [30] A more reliable synthesis of a Gemini vitamin D analog, a potentially effective chemotherapeutic agent for the treatment of colorectal carcinomas
    Santalla, Hugo
    Garrido, Fatima
    Gomez, Generosa
    Fall, Yagamare
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (13): : 2016 - 2019
12345