58701-45-4Relevant articles and documents
Synthesis of the fatty sterol bound protein for a new sterol antibody
Kim, Byung Ju,Yamada, Satoshi,Funada, Tadashi,Kadoma, Yoshihito,Morita, Hiroyuki
, p. 357 - 359 (2000)
For the purpose of applying the particular antibodies as a new diagnostic procedure for atherosclerosis and related diseases, we successfully achieved the synthesis of the fatty sterol with a linker, then linked the target protein to this sterol. Synthesis was started from pregnenolone and achieved by the Grignard reaction with pentenyl magnesium bromide, regioselective photo-addition of thiolacetic acid toward the 25-double bond, esterification of 3-OH with linoleic anhydride, in situ conjunction of the cross-linker (MBS) to the thiol group after selective deprotection from its acetyl ester, and finally by the reaction with protein such as KLH or albumin through this linker. (C) 2000 Elsevier Science Ltd. All rights reserved.
Synthesis of new C-25 and C-26 steroidal acids as potential ligands of the nuclear receptors DAF-12, LXR and GR
Dansey, María V.,del Fueyo, María C.,Veleiro, Adriana S.,Di Chenna, Pablo H.
, p. 40 - 46 (2017)
A new methodology to obtain C-25 and C-26 steroidal acids starting from pregnenolone is described. Construction of the side chain was achieved by applying the Mukaiyama aldol reaction with a non-hydrolytic work-up to isolate the trapped silyl enol ether with higher yields. Using this methodology we synthesized three new steroidal acids as potential ligands of DAF-12, Liver X and Glucocorticoid nuclear receptors and studied their activity in reporter gene assays. Our results show that replacement of the 21-CH3 by a 20-keto group in the side chains of the cholestane scaffold of DAF-12 or Liver X receptors ligands causes the loss of the activity.
Synthesis of withanolide A, biological evaluation of its neuritogenic properties, and studies on secretase inhibition
Jana, Chandan Kumar,Hoecker, Johannes,Woods, Tom M.,Jessen, Henning J.,Neuburger, Markus,Gademann, Karl
, p. 8407 - 8411 (2011)
Neurons on steroids: A stereoselective synthesis of the neuritogenic steroid lactone withanolide A was achieved by singlet oxygen ene reaction, Wharton transposition, a Corey-Seebach homologation, and a vinylogous aldol reaction. Biological evaluation demonstrated neurite outgrowth, which supports the potential neuritogenic role of this compound in traditional Indian medicine.
Elucidation of Distinct Modular Assemblies of Smoothened Receptor by Bitopic Ligand Measurement
Zhao, Fei,Wu, Yiran,Zhou, Fang,Xue, Dongxiang,Zhao, Simeng,Lu, Wanglong,Liu, Xiaoyan,Hu, Tao,Qiu, Yanli,Li, Rongyan,Gu, Tangjie,Xu, Yueming,Xu, Fei,Zhong, Guisheng,Jiang, Zhongxing,Zhao, Suwen,Tao, Houchao
supporting information, p. 13830 - 13840 (2021/09/28)
Class F G protein-coupled receptors are characterized by a large extracellular domain (ECD) in addition to the common transmembrane domain (TMD) with seven α-helixes. For smoothened receptor (SMO), structural studies revealed dissected ECD and TMD, and th
Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer
Lin, Zongtao,Marepally, Srinivasa R.,Ma, Dejian,Kim, Tae-Kang,Oak, Allen Sw.,Myers, Linda K.,Tuckey, Robert C.,Slominski, Andrzej T.,Miller, Duane D.,Li, Wei
supporting information, p. 5102 - 5108 (2016/06/13)
The vitamin D3 metabolite, 20S,23S-dihydroxyvitamin D3, was chemically synthesized for the first time and identified to be the same as the enzymatically produced metabolite. The C23 absolute configurations of both 20S,23S/R-dihydroxyvitamin D3 epimers were unambiguously assigned by NMR and Mosher ester analysis. Their kinetics of CYP27B1 metabolism were investigated during the production of their 1α-hydroxylated derivatives. Bioactivities of these products were compared in terms of vitamin D3 receptor activation, anti-inflammatory, and antiproliferative activities.
