TBTA
(Synonyms: 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺,TBTA) 目录号 : GC45003
TBTA是一种配体，能作为生化工具用于标记蛋白质和酶。TBTA也是点击加成的有效催化剂。
Cas No.:510758-28-8
Sample solution is provided at 25 µL, 10mM.
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TBTA is a ligand that can be used as a biochemical tool to label proteins and enzymes. TBTA is a tertiary amine containing a 1,2,3-triazole group. When used as a ligand, TBTA complexes with copper(I) and promotes catalysis by stabilizing the copper(I)-oxidation state to accelerate azide-alkyne cycloaddition reactions, as used in click chemistry [1].
References:
[1] Alireza Movahedi, et al. One-pot synthesis of TBTA-functionalized coordinating polymers. Reactive and Functional Polymers.2014. 82:1-8.
TBTA是一种配体，能作为生化工具用于标记蛋白质和酶。TBTA是含有1，2，3-三唑基团的叔胺。当TBTA用作配体时，与铜（I）络合并通过稳定铜（I）-氧化态来促进催化，以加速叠氮化物-炔环加成反应，如点击化学中所用 [1]。
| Cas No. | 510758-28-8 | SDF | |
| 别名 | 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺,TBTA | ||
| Canonical SMILES | C1(CN(CC2=CN(CC3=CC=CC=C3)N=N2)CC4=CN(CC5=CC=CC=C5)N=N4)=CN(CC6=CC=CC=C6)N=N1 | ||
| 分子式 | C30H30N10 | 分子量 | 530.6 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.8847 mL | 9.4233 mL | 18.8466 mL |
| 5 mM | 0.3769 mL | 1.8847 mL | 3.7693 mL |
| 10 mM | 0.1885 mL | 0.9423 mL | 1.8847 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Influencing the coordination mode of TBTA (TBTA = tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine) in dicobalt complexes through changes in metal oxidation states
Dalton Trans 2013 May 21;42(19):6944-52.PMID:23508268DOI:10.1039/c3dt00102d.
The complexes [(TBTA)Co(μ-CA(-2H))Co(TBTA)(CH3CN)](BF4)2 1 and [(TBTA)Co(μ-OH)2Co(TBTA)](BF4)4 2 (TBTA = tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine and CA = chloranilic acid) were synthesized and characterized by X-ray crystallography, SQUID magnetometry and NMR spectroscopy. The reactions to form these complexes deliver 1 as a paramagnetic species containing two high spin Co(II) centers, and 2 as a diamagnetic compound with two low spin Co(III) centers. Structural analysis shows that in 1 the capped-octahedral environment around the Co(II) centers is highly distorted with rather long bonds between the metal and donor atoms. The TBTA ligand binds to the Co(II) centers through the three triazole nitrogen donor atoms in a facial form, with the Co-N(amine) distance of 2.494(2) Å acting as a capping bond to the octahedron. In the crystal an unusual observation of one acetonitrile molecule statistically occupying the coordination sites at both Co(II) centers is made. 1 displays a series of intermolecular C-H···Cl and π-π interactions leading to extended three-dimensional structures in the solid state. These interactions lead to the formation of voids and explain why only one acetonitrile molecule can be bound to the dinuclear complexes. In contrast to 1, the cobalt centers in 2 display a more regular octahedral environment with shorter cobalt-donor atom distances, as would be expected for a low spin Co(III) situation. The TBTA ligand acts as a perfect tetradentate ligand in this case with the cobalt-N(amine) distance of 2.012(3) Å falling in the range of a normal bond. Thus, we present the rare instances where the ligand TBTA has been observed to bind in a perfectly tetradentate fashion in its metal complexes. The room temperature magnetic moment of 6.30 μB for 1 shows values typical of two high spin Co(II) centers, and this value decreases at temperatures lower than 30 K indicating a weak antiferromagnetic coupling and zero field splitting. Mass spectrometric analysis of 2 provided evidence for the formation of an oxo-bridged dicobalt complex in the gas phase.
Trabecular bone texture analysis of conventional radiographs in the assessment of knee osteoarthritis: review and viewpoint
Arthritis Res Ther 2021 Aug 6;23(1):208.PMID:34362427DOI:10.1186/s13075-021-02594-9.
Background: Trabecular bone texture analysis (TBTA) has been identified as an imaging biomarker that provides information on trabecular bone changes due to knee osteoarthritis (KOA). Consequently, it is important to conduct a comprehensive review that would permit a better understanding of this unfamiliar image analysis technique in the area of KOA research. We examined how TBTA, conducted on knee radiographs, is associated to (i) KOA incidence and progression, (ii) total knee arthroplasty, and (iii) KOA treatment responses. The primary aims of this study are twofold: to provide (i) a narrative review of the studies conducted on radiographic KOA using TBTA, and (ii) a viewpoint on future research priorities. Method: Literature searches were performed in the PubMed electronic database. Studies published between June 1991 and March 2020 and related to traditional and fractal image analysis of trabecular bone texture (TBT) on knee radiographs were identified. Results: The search resulted in 219 papers. After title and abstract scanning, 39 studies were found eligible and then classified in accordance to six criteria: cross-sectional evaluation of osteoarthritis and non-osteoarthritis knees, understanding of bone microarchitecture, prediction of KOA progression, KOA incidence, and total knee arthroplasty and association with treatment response. Numerous studies have reported the relevance of TBTA as a potential bioimaging marker in the prediction of KOA incidence and progression. However, only a few studies have focused on the association of TBTA with both OA treatment responses and the prediction of knee joint replacement. Conclusion: Clear evidence of biological plausibility for TBTA in KOA is already established. The review confirms the consistent association between TBT and important KOA endpoints such as KOA radiographic incidence and progression. TBTA could provide markers for enrichment of clinical trials enhancing the screening of KOA progressors. Major advances were made towards a fully automated assessment of KOA.
Ligand-assisted, copper(II) acetate-accelerated azide-alkyne cycloaddition
Chem Asian J 2011 Oct 4;6(10):2825-34.PMID:21954078DOI:10.1002/asia.201100426.
Polytriazole ligands such as the widely used tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA), are shown to assist copper(II) acetate-mediated azide-alkyne cycloaddition (AAC) reactions that involve nonchelating azides. Tris(2-{4-[(dimethylamino)methyl]-1H-1,2,3-traizol-1-yl}ethyl)amine (DTEA) outperforms TBTA in a number of reactions. The satisfactory solubility of DTEA in a wide range of polar and nonpolar solvents, including water and toluene, renders it advantageous under copper(II) acetate-mediated conditions. The copper(II) acetate-mediated formation of the three triazolyl groups in a tris(triazolyl)-based ligand occurs sequentially with an inhibitory effect in the last step. The kinetic investigations of the ligand-assisted reactions reveal an interesting mechanistic dependence on the relative affinity of azide and alkyne to copper (II). In addition to expanding the scope of the copper(II) acetate-mediated AAC reactions to include nonchelating azides, this work offers evidence for the mechanistic synergy between the title reaction and the alkyne oxidative homocoupling reaction. The elucidation of the structural details of the polytriazole-ligand-bound reactive species in copper(I/II)-mediated AAC reactions, however, awaits further characterization of the metal coordination chemistry of polytriazole ligands.
Spin crossover in Fe(II) and Co(II) complexes with the same click-derived tripodal ligand
Inorg Chem 2014 Aug 18;53(16):8203-12.PMID:25090159DOI:10.1021/ic500264k.
The complexes [Fe(TBTA)2](BF4)2·2EtOH (1), [Fe(TBTA)2](BF4)2·2CH3CN (2), [Fe(TBTA)2](BF4)2·2CHCl3 (3), and [Fe(TBTA)2](BF4)2 (4) were synthesized from the respective metal salts and the click-derived tripodal ligand tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA). Structural characterization of these complexes (at 100 or 133 K) revealed Fe-N bond lengths for the solvent containing compounds 1-3 that are typical of a high spin (HS) Fe(II) complex. In contrast, the solvent-free compound 4 show Fe-N bond lengths that are characteristic of a low spin (LS) Fe(II) state. The Fe center in all complexes is bound to two triazole and one amine N atom from each TBTA ligand, with the third triazole arm remaining uncoordinated. The benzyl substituents of the uncoordinated triazole arms and the triazole rings engage in strong intermolecular and intramolecular noncovalent interactions. These interactions are missing in the solvent containing molecules 1, 2, and 3, where the solvent molecules occupy positions that hinder these noncovalent interactions. The solvent-free complex (4) displays spin crossover (SCO) with a spin transition temperature T1/2 near room temperature, as revealed by superconducting quantum interference device (SQUID) magnetometric and Mössbauer spectroscopic measurements. The complexes 1, 2, and 3 remain HS throughout the investigated temperature range. Different torsion angles at the metal centers, which are influenced by the noncovalent interactions, are likely responsible for the differences in the magnetic behavior of these complexes. The corresponding solvent-free Co(II) complex (6) is also LS at lower temperatures and displays SCO with a temperature T1/2 near room temperature. Theoretical calculations at molecular and periodic DFT-D3 levels for 1-4 qualitatively reproduce the experimental findings, and corroborate the importance of intermolecular and intramolecular noncovalent interactions for the magnetic properties of these complexes. The present work thus represents rare examples of SCO complexes where the use of identical ligand sets produces SCO in Fe(II) as well as Co(II) complexes.
Effects of tributyltin acetate on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells
Arch Pharm Res 2007 Jul;30(7):858-65.PMID:17703738DOI:10.1007/BF02978837.
The effects of tributyltin acetate (TBTA) on dopamine biosynthesis and L-3,4-dihydroxyphenylalanine (L-DOPA)-induced cytotoxicity in PC12 cells were examined. TBTA at concentrations of 0.1-0.2 microM inhibited dopamine biosynthesis by reducing tyrosine hydroxylase (TH) activity and TH gene expression in PC12 cells. TBTA at 0.1-0.4 microM also reduced L-DOPA (20-50 microM)-induced increases in dopamine content for 24 h in PC12 cells. TBTA at concentrations up to 0.3 microM did not affect cell viability. However, TBTA at concentrations higher than 0.4 microM caused apoptotic cytotoxicity. Exposure of PC12 cells to non-cytotoxic (0.1 and 0.2 microM) or cytotoxic (0.4 microM) concentrations of TBTA with L-DOPA (20, 50 and 100 microM) significantly increased the cell loss and the percentage of apoptotic cells after 24 or 48 h compared with TBTA or L-DOPA alone. These data suggest that TBTA inhibits dopamine biosynthesis and enhances L-DOPA-induced cytotoxicity in PC12 cells.