(±)-caraphenol A

Names

[ Name ]:
(±)-caraphenol A

[Synonym ]:
Bisbenzofuro[3',4':4,5,6;3'',4'':7,8,9]cyclonona[1,2,3-cd]benzofuran-4,9,14-triol, 2,2a,7,7a-tetrahydro-2,7,12-tris(4-hydroxyphenyl)-, (2S,2aS,7R,7aR)-
(±)-caraphenol A
(2S,2aS,7R,7aR)-2,7,12-Tris(4-hydroxyphenyl)-2,2a,7,7a-tetrahydrobis[1]benzofuro[3',4':4,5,6;3'',4'':7,8,9]cyclonona[1,2,3-cd][1]benzofuran-4,9,14-triol

Biological Activity

[Description]:

Caraphenol A is a resveratrol trimer and is able to transiently reduce interferon-induced transmembrane (IFITM) protein expression. Caraphenol A safely enhances lentiviral vector gene delivery to hematopoietic stem and progenitor cells[1]. Caraphenol A also inhibits human cystathionine β-synthase (hCBS) and human cystathionine γ- lyase (hCSE) with IC50s of 5.9 μM and 12.1 μM, respectively[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[Target]

IFITM2, IFITM3[1] IC50: 5.9 μM (hCBS), 12.1 μM (hCSE)[2]

[In Vitro]

Caraphenol A (0-50 μM; 8 h) 增强慢病毒载体 (LV) 基因向 HeLa 的传递，但在 HEK293T 细胞中没有观察到相同作用[1]。 Caraphenol A 以依赖于内体转运的方式减少干扰素诱导的跨膜蛋白介导的限制[1]。 Caraphenol A 显著改善了低剂量和高剂量 LV 的造血干细胞 (HSC) 基因传递，而不改变 LV 整合模式[1]。 Caraphenol A (30 μM; 6 h) 促进慢病毒从核内体逃逸[1]。 Caraphenol A (30 μM; 4 h) 改变了 HeLa 细胞中 IFITM2/3 蛋白和晚期内小体的表达和亚细胞定位。Caraphenol A 对晚期核内体的影响取决于 IFITM3 的表达[1]。

[In Vivo]

Caraphenol A (30 μM; 预处理 4 h) 处理的造血干细胞在小鼠中保持改善的基因标记，而不改变慢病毒整合谱[1]。

[References]

[1]. Ozog S, et al. Resveratrol trimer enhances gene delivery to hematopoietic stem cells by reducing antiviral restriction at endosomes. Blood. 2019 Oct 17;134(16):1298-1311.

[2]. Niu W, et al. Discovery of selective cystathionine β-synthase inhibitors by high-throughput screening with a fluorescent thiol probe. Medchemcomm. 2016 Nov 15;8(1):198-201.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C₄₂H₂₈O₉

[ Molecular Weight ]:
676.666

[ Exact Mass ]:
676.173340

[ PSA ]:
152.98000

[ LogP ]:
6.50

[ Index of Refraction ]:
1.786

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds

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