生物素杂质27 | 21788-37-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 中文名称: 生物素杂质27
• 英文名称: vitamin H
• 英文别名: biotin；D-biotin；L-biotin；5-[(3aR,4R,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid
• CAS: 21788-37-4
• 化学式: C₁₀H₁₆N₂O₃S
• mdl: MFCD00063872
• 分子量: 244.315
• InChiKey: YBJHBAHKTGYVGT-ZXFLCMHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

L-生物素，又称生物素，是一种水溶性维生素，在多种酶的羧化反应中起到关键辅因子的作用。它参与脂肪酸合成及氨基酸代谢过程。

反应信息

• 作为反应物：
  描述：

  生物素杂质27 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 biotin acylchloride
  参考文献：
  名称：

  Biotinylated HPMA centered polymeric nanoparticles for Bortezomib delivery

  摘要：

  Bortezomib (BTZ) is a proteasome inhibitor as approved by US FDA for the treatment of multiple myeloma. It exhibits significant anti-cancer properties, against solid tumors; but lacks aqueous solubility, chemical stability which hinders its successful formulation development. The present study is an attempt to deliver BTZ using N-(2-hydroxypropyl) methacrylamide (HPMA) based copolymeric conjugates and biotinylated PNPs in an effective manner. Study describes a systematic synthetic pathway to synthesize functional polymeric conjugates such as HPMA-Biotin (HP-BT) HPMA-Polylactic acid (HPLA) and HPMA-PLA-Biotin (HPLA-BT) followed by exhaustive characterization both spectroscopically and microscopically. Our strategy yielded polymeric nanoparticles (PNPs) of narrow size range of 199.7 +/- 1.32 nm. Release studies were performed at pH 7.4 and 5.6. PNPs were 2-folds less hemolytic (p < 0.0001) than pure drug. BTZ loaded PNPs of HPLA-BT demonstrated significant anti-cancer activity against MCF-7 cells. IC50 value of these PNPs was 56.06 +/- 0.12 nM, which was approximately two folds less than BTZ (p < 0.0001). Cellular uptake study confirmed that higher uptake of formulations might be an outcome of biotin surface tethering characteristics that enhanced selectivity and targeting of formulations efficiently. In vivo pharmacokinetics evidenced increased bioavailability (AUC(0 t-infinity)) of DL-HPLA-BT PNPs (drug loaded) than BTZ with an improved half-life. Overall the developed PNPs led to the improved and effective BTZ delivery.

  DOI：

  10.1016/j.ijpharm.2020.119173
• 作为产物：
  描述：

  1'N-benzyl biotin 在 氨 、 sodium 、 xylene 作用下， 生成 生物素杂质27
  参考文献：
  名称：

  Synthesis of biotin

  摘要：

  公开号：

  US02489235A1

文献信息

• Compounds and Compositions for Modulating Lipid Levels and Methods of Preparing Same
  申请人：Liu Haiyan

  公开号：US20110009628A1

  公开（公告）日：2011-01-13

  The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.

  目前的技术涉及到公式I-VI的化合物以及制备和使用这些化合物的方法。使用方法包括预防和治疗高脂血症、高胆固醇血症、高甘油三酯血症、肝脂肪变性和代谢综合征。本文披露的化合物还可以增加高密度脂蛋白胆固醇（HDL-C），降低总胆固醇、低密度脂蛋白胆固醇（LDL-C）和甘油三酯，并增加肝LDL受体表达，抑制PCSK9表达，并激活AMP激活蛋白激酶。
• [EN] TARGETED THERAPEUTICS<br/>[FR] THÉRAPEUTIQUE CIBLÉE
  申请人：SYNTA PHARMACEUTICALS CORP

  公开号：WO2015038649A1

  公开（公告）日：2015-03-19

  The present invention provides pharmacological compounds including an effector moiety conjugated to a binding moiety that directs the effector moiety to a biological target of interest. Likewise, the present invention provides compositions, kits, and methods (e.g., therapeutic, diagnostic, and imaging) including the compounds. The compounds can be described as a protein interacting binding moiety-drug conjugate (SDC-TRAP) compounds, which include a protein interacting binding moiety and an effector moiety. For example, in certain embodiments directed to treating cancer, the SDC-TRAP can include an Hsp90 inhibitor conjugated to a cytotoxic agent as the effector moiety.

  本发明提供了包括与将效应子导向至感兴趣的生物靶点的结合基团共轭的药理化合物。同样，本发明提供了包括这些化合物的组合物、试剂盒和方法（例如治疗、诊断和成像）。这些化合物可以被描述为蛋白质相互作用结合基团-药物共轭（SDC-TRAP）化合物，其中包括蛋白质相互作用结合基团和效应子。例如，在针对治疗癌症的某些实施方式中，SDC-TRAP可以包括Hsp90抑制剂共轭到细胞毒性药剂作为效应子。
• Electrochemically enabled rhodium-catalyzed [4 + 2] annulations of arenes with alkynes
  作者：Zi-Chen Wang、Rui-Tao Li、Qiang Ma、Jia-Yi Chen、Shao-Fei Ni、Ming Li、Li-Rong Wen、Lin-Bao Zhang

  DOI：10.1039/d1gc03187b

  日期：——

  Herein, electrochemically driven, Rh(iii)-catalyzed regioselective annulations of arenes with alkynes have been established.

  在这里，已建立了通过电化学驱动的Rh(iii)催化的芳烃与炔烃的区域选择性环化反应。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING NASH, NAFLD, AND OBESITY<br/>[FR] COMPOSÉS, COMPOSITIONS ET MÉTHODES DE TRAITEMENT DE LA NASH, DE LA NAFLD ET DE L'OBÉSITÉ
  申请人：LIU JINGWEN

  公开号：WO2021067490A1

  公开（公告）日：2021-04-08

  The present technology relates to methods of treating NASH, NAFLD and/or obesity using compounds of Formulas I, II, III, IV, V, and/or VI. The methods include administering to a subject suffering from one or more of non-alcoholic steatohepatitis (NASH), non- alcoholic fatty liver disease (NAFLD) and/or obesity a therapeutically effective amount of such a compound

  目前的技术涉及使用I、II、III、IV、V和/或VI式化合物治疗NASH、NAFLD和/或肥胖的方法。这些方法包括向患有非酒精性脂肪肝炎（NASH）、非酒精性脂肪肝病（NAFLD）和/或肥胖的受试者施用这种化合物的治疗有效剂量。
• Using chemical probes to investigate the sub-inhibitory effects of azithromycin
  作者：Freija G. Glansdorp、Richard J. Spandl、Jane E. Swatton、Olivier Loiseleur、Martin Welch、David R. Spring

  DOI：10.1039/b813157k

  日期：——

  The antibacterial drug azithromycin has clinically beneficial effects at sub-inhibitory concentrations for the treatment of conditions characterized by chronic Pseudomonas aeruginosa infection, such as cystic fibrosis. These effects are, in part, the result of inhibition of bacterial biofilm formation. Herein, the efficient synthesis of azithromycin in 4 steps from erythromycin and validation of the drug's ability to inhibit biofilm formation at sub-MIC (minimum inhibitory concentration) values are reported. Furthermore, the synthesis of immobilized and biotin-tagged azithromycin analogues is described. These chemical probes were used in pull-down assays in an effort to identify azithromycin's binding partners in vivo. Results from these assays revealed, as expected, mainly ribosomal-related protein binding partners, suggesting that this is the primary target of the drug. This was further confirmed by studies using a P. aeruginosa strain containing plasmid-encoded ermC, which expresses a protein that modifies 23S rRNA and so blocks macrolide entry to the ribosome. In this strain, no biofilm inhibition was observed. This work supports the hypothesis that the sub-inhibitory effects of azithromycin are mediated through the ribosome. Moreover, the synthesis of these chemical probes, and proof of their utility, is of value in global target identification in P. aeruginosa and other species.

  抗菌药物阿奇霉素在亚抑制浓度下对治疗以慢性铜绿假单胞菌感染为特征的疾病，如囊性纤维化，具有临床益处。这些效果部分是由于抑制了细菌生物膜的形成。本文报道了从红霉素出发经4步高效合成阿奇霉素，并验证了其在亚最低抑菌浓度（MIC）值下抑制生物膜形成的能力。此外，还描述了固定化和生物素标记的阿奇霉素类似物的合成。这些化学探针用于下拉实验，以努力鉴定阿奇霉素在体内的结合伙伴。正如预期的那样，这些实验结果主要揭示了与核糖体相关的蛋白质结合伙伴，表明这是该药物的主要靶点。这一发现通过使用一种含有质粒编码的ermC的铜绿假单胞菌株进一步证实，该菌株表达一种修饰23S rRNA的蛋白质，从而阻止大环内酯类进入核糖体。在这种菌株中，未观察到生物膜抑制现象。这项工作支持了阿奇霉素亚抑制效应是通过核糖体介导的假设。此外，合成这些化学探针并证明其效用，在全球目标识别中对铜绿假单胞菌和其他物种具有价值。