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1
1alpha,25-Dihydroxyvitamin D(3)-26,23-lactam analogues function as vitamin D receptor antagonists in human and rodent cells.1α,25-二羟基维生素D(3)-26,23-内酰胺类似物在人和啮齿动物细胞中作为维生素D受体拮抗剂发挥作用。
J Steroid Biochem Mol Biol. 2008 Jun;110(3-5):269-77. doi: 10.1016/j.jsbmb.2007.11.007. Epub 2008 Apr 22.
2
Novel vitamin D3 analogs, 1alpha, 25(OH)2D(3)-26, 23-lactam (DLAMs), antagonize bone resorption via suppressing RANKL expression in osteoblasts.新型维生素D3类似物，1α,25(OH)2D(3)-26,23-内酰胺（DLAMs），通过抑制成骨细胞中RANKL的表达来拮抗骨吸收。
Biochem Biophys Res Commun. 2008 Aug 1;372(3):434-9. doi: 10.1016/j.bbrc.2008.05.041. Epub 2008 May 19.
3
Antagonistic action of novel 1alpha,25-dihydroxyvitamin D3-26, 23-lactone analogs on differentiation of human leukemia cells (HL-60) induced by 1alpha,25-dihydroxyvitamin D3.新型1α,25 - 二羟基维生素D3 - 26,23 - 内酯类似物对1α,25 - 二羟基维生素D3诱导的人白血病细胞（HL - 60）分化的拮抗作用
J Biol Chem. 1999 Jun 4;274(23):16392-9. doi: 10.1074/jbc.274.23.16392.
4
Synthesis of 1alpha,25-dihydroxyvitamin D3-26,23-lactams (DLAMs), a novel series of 1 alpha,25-dihydroxyvitamin D3 antagonist.新型1α,25-二羟基维生素D3拮抗剂1α,25-二羟基维生素D3-26,23-内酰胺（DLAMs）的合成
Bioorg Med Chem Lett. 2004 May 17;14(10):2579-83. doi: 10.1016/j.bmcl.2004.02.076.
5
(23S)-25-Dehydro-1{alpha}-hydroxyvitamin D3-26,23-lactone, a vitamin D receptor antagonist that inhibits osteoclast formation and bone resorption in bone marrow cultures from patients with Paget's disease.（23S）-25-脱氢-1α-羟基维生素D3-26,23-内酯，一种维生素D受体拮抗剂，可抑制佩吉特病患者骨髓培养物中破骨细胞的形成和骨吸收。
Endocrinology. 2005 Apr;146(4):2023-30. doi: 10.1210/en.2004-1140. Epub 2004 Dec 23.
6
(23S)- and (23R)-25-dehydro-1alpha-hydroxyvitamin D(3)-26,23-lactone function as antagonists of vitamin D receptor-mediated genomic actions of 1alpha,25-dihydroxyvitamin D(3).（23S）-和（23R）-25-脱氢-1α-羟基维生素D（3）-26,23-内酯作为1α,25-二羟基维生素D（3）的维生素D受体介导的基因组作用的拮抗剂。
Steroids. 2001 Mar-May;66(3-5):227-37. doi: 10.1016/s0039-128x(00)00146-x.
7
Antagonistic action of novel 1alpha,25-dihydroxyvitamin D(3)-26, 23-lactone analogs on 25-hydroxyvitamin-D(3)-24-hydroxylase gene expression induced by 1alpha,25-dihydroxy-vitamin D(3) in human promyelocytic leukemia (HL-60) cells.新型1α,25-二羟基维生素D(3)-26,23-内酯类似物对1α,25-二羟基维生素D(3)诱导的人早幼粒细胞白血病（HL-60）细胞中25-羟基维生素D(3)-24-羟化酶基因表达的拮抗作用。
Arch Biochem Biophys. 2000 Aug 1;380(1):92-102. doi: 10.1006/abbi.2000.1902.
8
Structure-activity relationship studies on vitamin D lactam derivatives as vitamin D receptor antagonist.维生素D内酰胺衍生物作为维生素D受体拮抗剂的构效关系研究
Bioorg Med Chem Lett. 2008 Aug 1;18(15):4287-90. doi: 10.1016/j.bmcl.2008.06.095. Epub 2008 Jul 3.
9
Practical synthesis and evaluation of the biological activities of 1alpha,25-dihydroxyvitamin D3 antagonists, 1alpha,25-dihydroxyvitamin D3-26,23-lactams. Designed on the basis of the helix 12-folding inhibition hypothesis.1α,25 - 二羟基维生素D3拮抗剂1α,25 - 二羟基维生素D3 - 26,23 - 内酰胺的生物活性的实用合成与评估。基于螺旋12折叠抑制假说设计。
J Med Chem. 2006 Apr 20;49(8):2398-406. doi: 10.1021/jm050738x.
10
1alpha,25-dihydroxyvitamin D(3)-26,23-lactone analogs antagonize differentiation of human leukemia cells (HL-60 cells) but not of human acute promyelocytic leukemia cells (NB4 cells).1α,25-二羟基维生素D(3)-26,23-内酯类似物可拮抗人白血病细胞（HL-60细胞）的分化，但对人急性早幼粒细胞白血病细胞（NB4细胞）则无此作用。
FEBS Lett. 1999 Oct 29;460(2):297-302. doi: 10.1016/s0014-5793(99)01347-2.

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Role of Vitamin D in Cognitive Dysfunction: New Molecular Concepts and Discrepancies between Animal and Human Findings.维生素 D 在认知功能障碍中的作用：新的分子概念和动物与人类研究结果之间的差异。
Nutrients. 2021 Oct 20;13(11):3672. doi: 10.3390/nu13113672.
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Inhibitors for the Vitamin D Receptor-Coregulator Interaction.维生素D受体-共调节因子相互作用的抑制剂
Vitam Horm. 2016;100:45-82. doi: 10.1016/bs.vh.2015.10.002. Epub 2015 Nov 30.
3
Vitamin D represses dentin matrix protein 1 in cementoblasts and osteocytes.维生素 D 抑制成牙本质细胞和骨细胞中的牙本质基质蛋白 1。
J Dent Res. 2014 Feb;93(2):148-54. doi: 10.1177/0022034513516344. Epub 2013 Dec 11.
4
Vitamin D3-driven signals for myeloid cell differentiation--implications for differentiation therapy.维生素 D3 驱动的髓系细胞分化信号——对分化治疗的启示。
Leuk Res. 2010 May;34(5):553-65. doi: 10.1016/j.leukres.2009.09.010. Epub 2009 Oct 6.

本文引用的文献

1
Practical synthesis and evaluation of the biological activities of 1alpha,25-dihydroxyvitamin D3 antagonists, 1alpha,25-dihydroxyvitamin D3-26,23-lactams. Designed on the basis of the helix 12-folding inhibition hypothesis.1α,25 - 二羟基维生素D3拮抗剂1α,25 - 二羟基维生素D3 - 26,23 - 内酰胺的生物活性的实用合成与评估。基于螺旋12折叠抑制假说设计。
J Med Chem. 2006 Apr 20;49(8):2398-406. doi: 10.1021/jm050738x.
2
Molecular mechanism of the vitamin D antagonistic actions of (23S)-25-dehydro-1alpha-hydroxyvitamin D3-26,23-lactone depends on the primary structure of the carboxyl-terminal region of the vitamin d receptor.（23S）-25-脱氢-1α-羟基维生素D3-26,23-内酯的维生素D拮抗作用的分子机制取决于维生素D受体羧基末端区域的一级结构。
Mol Endocrinol. 2005 May;19(5):1147-57. doi: 10.1210/me.2004-0234. Epub 2005 Jan 13.
3
(23S)-25-Dehydro-1{alpha}-hydroxyvitamin D3-26,23-lactone, a vitamin D receptor antagonist that inhibits osteoclast formation and bone resorption in bone marrow cultures from patients with Paget's disease.（23S）-25-脱氢-1α-羟基维生素D3-26,23-内酯，一种维生素D受体拮抗剂，可抑制佩吉特病患者骨髓培养物中破骨细胞的形成和骨吸收。
Endocrinology. 2005 Apr;146(4):2023-30. doi: 10.1210/en.2004-1140. Epub 2004 Dec 23.
4
A structural basis for the species-specific antagonism of 26,23-lactones on vitamin D signaling.26,23-内酯对维生素D信号传导的物种特异性拮抗作用的结构基础。
Chem Biol. 2004 Aug;11(8):1147-56. doi: 10.1016/j.chembiol.2004.05.023.
5
Vitamin D antagonist, TEI-9647, inhibits osteoclast formation induced by 1alpha,25-dihydroxyvitamin D3 from pagetic bone marrow cells.维生素D拮抗剂TEI-9647可抑制畸形性骨炎骨髓细胞中1α,25-二羟基维生素D3诱导的破骨细胞形成。
J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):331-4. doi: 10.1016/j.jsbmb.2004.03.025.
6
Ligand-mediated conformational changes of the VDR are required for gene transactivation.配体介导的维生素D受体构象变化是基因反式激活所必需的。
J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):227-32. doi: 10.1016/j.jsbmb.2004.03.112.
7
Role of TAFII-17, a VDR binding protein, in the increased osteoclast formation in Paget's Disease.TAFII-17（一种维生素D受体结合蛋白）在佩吉特病破骨细胞形成增加中的作用。
J Bone Miner Res. 2004 Jul;19(7):1154-64. doi: 10.1359/JBMR.040312. Epub 2004 Mar 15.
8
Synthesis of 1alpha,25-dihydroxyvitamin D3-26,23-lactams (DLAMs), a novel series of 1 alpha,25-dihydroxyvitamin D3 antagonist.新型1α,25-二羟基维生素D3拮抗剂1α,25-二羟基维生素D3-26,23-内酰胺（DLAMs）的合成
Bioorg Med Chem Lett. 2004 May 17;14(10):2579-83. doi: 10.1016/j.bmcl.2004.02.076.
9
Critical role of helix 12 of the vitamin D(3) receptor for the partial agonism of carboxylic ester antagonists.维生素D(3)受体的螺旋12对羧酸酯拮抗剂部分激动作用的关键作用。
J Mol Biol. 2002 Jan 11;315(2):229-38. doi: 10.1006/jmbi.2001.5225.
10
Different molecular mechanisms of vitamin D(3) receptor antagonists.维生素D(3)受体拮抗剂的不同分子机制。
Mol Pharmacol. 2001 Jun;59(6):1478-85. doi: 10.1124/mol.59.6.1478.

1α,25-二羟基维生素D(3)-26,23-内酰胺类似物在人和啮齿动物细胞中作为维生素D受体拮抗剂发挥作用。

1alpha,25-Dihydroxyvitamin D(3)-26,23-lactam analogues function as vitamin D receptor antagonists in human and rodent cells.

作者信息

Ishizuka Seiichi, Kurihara Noriyoshi, Hiruma Yuko, Miura Daishiro, Namekawa Jun-ichi, Tamura Azusa, Kato-Nakamura Yuko, Nakano Yusuke, Takenouchi Kazuya, Hashimoto Yuichi, Nagasawa Kazuo, Roodman G David

机构信息

Teijin Institute for Bio-Medical Research, Hino, Tokyo, Japan.

出版信息

J Steroid Biochem Mol Biol. 2008 Jun;110(3-5):269-77. doi: 10.1016/j.jsbmb.2007.11.007. Epub 2008 Apr 22.

DOI:10.1016/j.jsbmb.2007.11.007
PMID:18501591
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2530904/
Abstract

(23S,25S)-N-Benzyl-1alpha,25-dihydroxyvitamin D(3)-26,23-lactam ((23S,25S)-N-benzyl-1alpha,25-(OH)(2)D(3)-26,23-lactam, (23S,25S)-DLAM-1P) antagonizes nuclear vitamin D receptor (VDR)-mediated differentiation of human promyelocytic leukemia (HL-60) cells [Y. Kato, Y. Nakano, H. Sano, A. Tanatani, H. Kobayashi, R. Shimazawa, H. Koshino, Y. Hashimoto, K. Nagasawa, Synthesis of 1alpha,25-dihydroxy vitamin D(3)-26,23-lactams (DLAMs), a novel series of 1alpha,25-dihydroxy vitamin D(3) antagonist, Bioorg. Med. Chem. Lett. 14 (2004) 2579-2583]. To enhance its VDR antagonistic actions, we synthesized multiple analogues of 1alpha,25-(OH)(2)D(3)-26,23-lactam. Among these analogues, (23S,25S)-N-phenetyl-1alpha,25-(OH)(2)D(3)-26,23-lactam, ((23S,25S)-DLAM-2P) had the strongest VDR binding affinity, which was 3 times higher than that of (23S,25S)-DLAM-1P. The 1alpha,25-(OH)(2)D(3)-26,23-lactam analogues never induced HL-60 cell differentiation even at 10(-6)M, but (23S,25S)-DLAM-1P and (23S,25S)-DLAM-2P significantly and dose-dependently inhibited HL-60 differentiation induced by 10(-8)M 1alpha,25-dihydroxyvitamin D(3) (1alpha,25-(OH)(2)D(3)). These compounds also inhibited human and mouse cultures of osteoclast formation by marrow cells treated with 1alpha,25-(OH)(2)D(3). Moreover, the 1alpha,25-(OH)(2)D(3)-26,23-lactam analogues minimally induced 25-hydroxyvitamin D(3)-24-hydroxylase gene expression in HL-60 cells and human and mouse osteoblastic cells, but 10(-6)M (23S,25S)-DLAM-1P or (23S,25S)-DLAM-2P significantly blocked 24-hydroxylase gene expression induced by 10(-8)M 1alpha,25-(OH)(2)D(3). (23S,25S)-DLAM-2P was 5-12 times more potent as a vitamin D antagonist than (23S,25S)-DLAM-1P in HL-60 cells, human and mouse bone marrow cultures. These results demonstrate that (23S,25S)-DLAM-1P and (23S,25S)-DLAM-2P antagonize HL-60 cell differentiation and osteoclast formation by human and mouse osteoclast precursors induced by 1alpha,25-(OH)(2)D(3) through blocking VDR-mediated gene transcription. In contrast, (23S)-25-deoxy-1alpha-hydroxyvitamin D(3)-26,23-lactone, which only blocks human VDR, these vitamin D antagonists can block VDR in human cells and rodent cells.

摘要

(23S,25S)-N-苄基-1α,25-二羟基维生素D(3)-26,23-内酰胺（(23S,25S)-N-苄基-1α,25-(OH)(2)D(3)-26,23-内酰胺，(23S,25S)-DLAM-1P）可拮抗核维生素D受体（VDR）介导的人早幼粒细胞白血病（HL-60）细胞分化[Y. 加藤，Y. 中野，H. 佐野，A. 塔纳塔尼，H. 小林，R. 岛泽，H. 小筱，Y. 桥本，K. 长泽，新型1α,25-二羟基维生素D(3)拮抗剂1α,25-二羟基维生素D(3)-26,23-内酰胺（DLAMs）的合成，生物有机与药物化学快报14 (2004) 2579 - 2583]。为增强其VDR拮抗作用，我们合成了1α,25-(OH)(2)D(3)-26,23-内酰胺的多种类似物。在这些类似物中，(23S,25S)-N-苯乙基-1α,25-(OH)(2)D(3)-26,23-内酰胺（(23S,25S)-DLAM-2P）具有最强的VDR结合亲和力，比(23S,25S)-DLAM-1P高3倍。1α,25-(OH)(2)D(3)-26,23-内酰胺类似物即使在10(-6)M时也从未诱导HL-60细胞分化，但(23S,25S)-DLAM-1P和(23S,25S)-DLAM-2P显著且剂量依赖性地抑制10(-8)M 1α,25-二羟基维生素D(3)（1α,25-(OH)(2)D(3)）诱导的HL-60分化。这些化合物还抑制了用1α,25-(OH)((2)D(3)处理的骨髓细胞形成人及小鼠破骨细胞。此外，1α,25-(OH)(2)D(3)-26,23-内酰胺类似物在HL-60细胞以及人和小鼠成骨细胞中极少诱导2-5-羟基维生素D(3)-24-羟化酶基因表达，但10(-6)M (23S,25S)-DLAM-1P或(23S,25S)-DLAM-2P显著阻断10(-8)M 1α,（25）-(OH)(2)D(3)诱导的24-羟化酶基因表达。在HL-60细胞、人和小鼠骨髓培养物中，(23S,25S)-DLAM-2P作为维生素D拮抗剂的效力比(23S,25S)-DLAM-1P高5 - 12倍。这些结果表明，(23S,25S)-DLAM-1P和(23S,25S)-DLAM-2P通过阻断VDR介导的基因转录，拮抗1α,25-(OH)((2)D(3)诱导的HL-60细胞分化以及人和小鼠破骨细胞前体形成破骨细胞。相比之下，仅阻断人VDR的(23S)-25-脱氧-1α-羟基维生素D(3)-26,23-内酯，这些维生素D拮抗剂可阻断人细胞和啮齿动物细胞中的VDR。