6-bromo-6-deoxy-α,α'-trehalose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-6-deoxy-α,α'-trehalose
• 英文别名: 6-deoxy-6-bromo-α,α’-trehalose；6-Bromo-6-deoxy-alpha,alpha-D-trehalose；(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6S)-6-(bromomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₂H₂₁BrO₁₀
• 分子量: 405.197
• InChiKey: MDGZDHHFUFLZSK-LIZSDCNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-bromo-6-deoxy-α,α'-trehalose 在 sodium azide 作用下， 以 水 为溶剂， 反应 4.0h， 以90%的产率得到6-Azido-6-Deoxy-α,α-D-trehalose
  参考文献：
  名称：

  Ratiometric fluorescence sensing and cellular imaging of Cu2+ by a new water soluble trehalose-naphthalimide based chemosensor

  摘要：

  合成了一种新型的开启型铜离子（Cu2+）荧光传感器（CST），其具有一个海藻糖部分，使其在水中的溶解度相对较大。因此，该化学传感器适合在水溶液中进行研究。全面的电位计和紫外-可见光特征表明，在生理pH下，CST与Cu2+形成一种1:1的化合物，使得CST的反应与铜（II）浓度之间可以进行直接的关联。海藻糖单位的存在并没有对CST在一系列感兴趣金属离子中对Cu2+的选择性产生负面影响， fluorescence 测量证明了这一点。在分化的神经母细胞瘤SH-SY5Y细胞中测试的新型化学传感器能够检测细胞外区的Cu2+，并能够跟踪细胞去极化诱导下的细胞刺激过程中的铜转运过程。

  DOI：

  10.1039/c3ra43988g
• 作为产物：
  描述：

  海藻糖 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-bromo-6-deoxy-α,α'-trehalose
  参考文献：
  名称：

  针对HIV-1的TAR RNA的胍基糖苷的设计与合成

  摘要：

  复制人类1型免疫缺陷病毒（HIV-1）需要Tat蛋白与反式激活区（TAR）RNA的特异性相互作用。Tat-TAR RNA相互作用是由蛋白质的富含精氨酸的短域介导的。从理论上讲，这种相互作用的中断可能会导致完全病毒潜伏期的状态。这里，四种新型6-氨基-6- deoxytrehalose guanidinoglycoside衍生物（10和13 - 15）作为目标分子已被设计成结合到TAR RNA用于阻挡TAT-TAR RNA的相互作用。它们是通过偶联6-氨基-6-脱氧-α，α-海藻糖（6用保护的氨基酸），通过催化氢化脱保护，然后用S-甲基异硫脲硫酸盐进行胍基化。通过抑制依赖Tat的HIV-1长末端重复序列（LTR）驱动的氯霉素乙酰转移酶（CAT）测定来确定它们抑制Tat-TAR RNA相互作用的能力。

  DOI：

  10.1002/hlca.200390213

文献信息

• [EN] DETECTION OF MYCOBACTERIA<br/>[FR] DÉTECTION DE MYCOBACTÉRIES
  申请人：ISIS INNOVATION

  公开号：WO2011030160A1

  公开（公告）日：2011-03-17

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌种类存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标记，该探针分子可以被结核分枝杆菌所吸收，通过对标记的存在做出反应的探测器确定结核分枝杆菌的存在，可选地，在施加刺激后进行；适用的探针分子包括包含标记和底物的化合物，该标记可以被对标记的存在做出反应的探测器检测到，可选地，在施加刺激后进行，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点结合，从而能够与所选活性位点中的两个或更多氨基酸同时形成氢键，所选活性位点包括Arg 43、Trp 264、Ser126、His 262和Leu 42，或者抗原85A（Ag85A）或抗原85C（Ag85C）中对应的氨基酸，其中至少一个与Ser126形成氢键。
• Design and Synthesis of Guanidinoglycosides Directed against the TAR RNA of HIV-1
  作者：Min Wang、Peng-Fei Tu、Zhi-Dong Xu、Xiao-Lin Yu、Ming Yang

  DOI：10.1002/hlca.200390213

  日期：2003.7

  molecules have been designed to bind to TAR RNA for blocking the interaction of Tat-TAR RNA. They were obtained by coupling 6-amino-6-deoxy-α,α-trehalose (6) with the protected amino acids, deprotection by catalytic hydrogenation, followed by guanidinylated with S-methylisothiourea sulfate. Their abilities to inhibit Tat-TAR RNA interaction were determined by a Tat-dependent HIV-1 long terminal repeats

  复制人类1型免疫缺陷病毒（HIV-1）需要Tat蛋白与反式激活区（TAR）RNA的特异性相互作用。Tat-TAR RNA相互作用是由蛋白质的富含精氨酸的短域介导的。从理论上讲，这种相互作用的中断可能会导致完全病毒潜伏期的状态。这里，四种新型6-氨基-6- deoxytrehalose guanidinoglycoside衍生物（10和13 - 15）作为目标分子已被设计成结合到TAR RNA用于阻挡TAT-TAR RNA的相互作用。它们是通过偶联6-氨基-6-脱氧-α，α-海藻糖（6用保护的氨基酸），通过催化氢化脱保护，然后用S-甲基异硫脲硫酸盐进行胍基化。通过抑制依赖Tat的HIV-1长末端重复序列（LTR）驱动的氯霉素乙酰转移酶（CAT）测定来确定它们抑制Tat-TAR RNA相互作用的能力。
• DETECTION OF MYCOBACTERIA
  申请人：Backus Keriann Marie

  公开号：US20120263649A1

  公开（公告）日：2012-10-18

  A method for determining the presence of mycobacteria species in an organism or biological sample, the method comprising adding to the organism or biological sample a probe molecule comprising a substrate and a label, which probe molecule can be incorporated into mycobacteria, the presence of mycobacteria being determined by a detector responsive to the presence of the label, optionally after applying a stimulus; suitable probe molecules include compounds comprising a label and a substrate, which label is can be detected by a detector responsive to the presence of the label, optionally after applying a stimulus, characterised by compound being able to engage with the active site of Antigen 85B (Ag85B) such that it can form simultaneous hydrogen bonds with two or more amino acids in the active site selected from Arg 43, Trp 264, Ser126, His 262 and Leu 42, or the corresponding amino acids in Antigen 85A (Ag85A) or Antigen 85C (Ag85C), at least one of which is with Ser126.

  一种用于确定生物体或生物样本中结核分枝杆菌物种存在的方法，该方法包括向生物体或生物样本中添加一种探针分子，该探针分子包括底物和标签，该探针分子可以被结核分枝杆菌所包含，通过对响应标签存在的探测器进行检测来确定结核分枝杆菌的存在，可选地，在施加刺激后进行检测；适当的探针分子包括包含标签和底物的化合物，该标签可以被响应标签存在的探测器检测到，可选地，在施加刺激后进行检测，其特征在于该化合物能够与抗原85B（Ag85B）的活性位点发生作用，使其能够与活性位点中的Arg 43、Trp 264、Ser126、His 262和Leu 42中选择的两个或更多氨基酸同时形成氢键，或与抗原85A（Ag85A）或抗原85C（Ag85C）中的相应氨基酸形成氢键，其中至少有一个与Ser126形成氢键。
• Trehalose–Carnosine Prevents the Effects of Spinal Cord Injury Through Regulating Acute Inflammation and Zinc(II) Ion Homeostasis
  作者：Irene Paterniti、Alessia Filippone、Irina Naletova、Valentina Greco、Sebastiano Sciuto、Emanuela Esposito、Salvatore Cuzzocrea、Enrico Rizzarelli

  DOI：10.1007/s10571-022-01273-w

  日期：——

  Spinal cord injury (SCI) leads to long-term and permanent motor dysfunctions, and nervous system abnormalities. Injury to the spinal cord triggers a signaling cascade that results in activation of the inflammatory cascade, apoptosis, and Zn(II) ion homeostasis. Trehalose (Tre), a nonreducing disaccharide, and l-carnosine (Car), (β-alanyl-l-histidine), one of the endogenous histidine dipeptides have been recognized to suppress early inflammatory effects, oxidative stress and to possess neuroprotective effects. We report on the effects of the conjugation of Tre with Car (Tre–car) in reducing inflammation in in vitro and in vivo models. The in vitro study was performed using rat pheochromocytoma cells (PC12 cell line). After 24 h, Tre–car, Car, Tre, and Tre + Car mixture treatments, cells were collected and used to investigate Zn²⁺ homeostasis. The in vivo model of SCI was induced by extradural compression of the spinal cord at the T6–T8 levels. After treatments with Tre, Car and Tre–Car conjugate 1 and 6 h after SCI, spinal cord tissue was collected for analysis. In vitro results demonstrated the ionophore effect and chelating features of l-carnosine and its conjugate. In vivo, the Tre–car conjugate treatment counteracted the activation of the early inflammatory cascade, oxidative stress and apoptosis after SCI. The Tre–car conjugate stimulated neurotrophic factors release, and influenced Zn²⁺ homeostasis. We demonstrated that Tre–car, Tre and Car treatments improved tissue recovery after SCI. Tre–car decreased proinflammatory, oxidative stress mediators release, upregulated neurotrophic factors and restored Zn²⁺ homeostasis, suggesting that Tre–car may represent a promising therapeutic agent for counteracting the consequences of SCI.

  标题：摘要 脊髓损伤（SCI）会导致长期和永久的运动功能障碍和神经系统异常。脊髓损伤会触发信号级联反应，导致炎症级联反应、细胞凋亡和Zn（II）离子稳态失衡。特雷哈罗斯（Tre）是一种非还原二糖，而β-丙氨酸- L-组氨酸（Car）是内源性组氨酸二肽之一，已被认为可以抑制早期炎症效应、氧化应激并具有神经保护作用。我们报告了Tre与Car（Tre-car）的结合对于体外和体内模型中减少炎症的影响。体外研究使用大鼠嗜铬细胞瘤细胞（PC12细胞系）进行，24小时后，Tre-car、Car、Tre和Tre+Car混合物处理后，收集细胞并用于研究Zn2+稳态。SCI的体内模型是通过在T6-T8水平压迫脊髓引起的。SCI后1小时和6小时给予Tre、Car和Tre-Car结合物治疗后，收集脊髓组织进行分析。体外结果表明了L-肉碱的离子载体效应和螯合特性及其结合物。在体内，Tre-car结合物治疗对抗了SCI后早期炎症级联反应、氧化应激和细胞凋亡。Tre-car结合物刺激神经营养因子的释放，并影响了Zn2+稳态。我们证明了Tre-car、Tre和Car治疗可以改善SCI后的组织恢复。Tre-car减少了促炎症、氧化应激介质的释放，上调了神经营养因子并恢复了Zn2+稳态，表明Tre-car可能是一种有前途的治疗剂，可以对抗SCI的后果。
• Terpyridine Glycoconjugates and Their Metal Complexes: Antiproliferative Activity and Proteasome Inhibition
  作者：Roberta Panebianco、Maurizio Viale、Fabrizio Loiacono、Valeria Lanza、Danilo Milardi、Graziella Vecchio

  DOI：10.1002/cmdc.202200701

  日期：——

  antitumor agents. Our results highlight that Cu(II) and Fe(II) ternary complexes of terpyridine derivatives have antiproliferative activity in the micromolar range. Additionally, parent terpyridine compounds have been assayed as proteasome modulators. [Cu(TpyCl)2]2+ exhibited an inhibition profile of proteasomal chymotrypsin activity in the nanomolar range. It may be a possible antineoplastic mechanism

  糖和金属：三联吡啶糖缀合物已被证明是潜在的抗肿瘤剂。我们的结果强调三联吡啶衍生物的 Cu(II) 和 Fe(II) 三元配合物在微摩尔范围内具有抗增殖活性。此外，母体三联吡啶化合物已被测定为蛋白酶体调节剂。[Cu(TpyCl) 2 ] 2+在纳摩尔范围内表现出对蛋白酶体胰凝乳蛋白酶活性的抑制作用。这可能是一种可能的抗肿瘤机制。