TFM
(Synonyms: 3-三氟甲基-4-硝基苯酚) 目录号 : GC48924
A piscicide
Cas No.:88-30-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
TFM is a piscicide.1 It is toxic to sea lamprey (P. marinus) with LC50 values ranging from 1.97 to 2.11 and 2.05 to 2.21 mg/L for sac and swim-up fry, respectively, 1.6 to 2.45 mg/L for juveniles, and 1.6 to 1.63 mg/L for adults. It is also toxic to juvenile lake sturgeon (A. fulvescens) less than 100 mm in size but not to a variety of other fish species. TFM (50 µM) uncouples oxidative phosphorylation by 22 and 28% in isolated sea lamprey and rainbow trout (O. mykiss) liver, respectively.2 Formulations containing TFM have been used as lampricides in the control of larval sea lamprey populations.
1.Boogaard, M.A., Bills, T.D., and Johnson, D.A.Acute toxicity of TFM and a TFM/niclosamide mixture to selected species of fish, including lake sturgeon (Acipenser fulvescens) and mudpuppies (Necturus maculosus), in laboratory and field exposuresJ. Great Lakes Res.29(Suppl 1)529-541(2003) 2.Birceanu, O., McClelland, G.B., Wang, Y.S., et al.The lampricide 3-trifluoromethyl-4-nitrophenol (TFM) uncouples mitochondrial oxidative phosphorylation in both sea lamprey (Petromyzon marinus) and TFM-tolerant rainbow trout (Oncorhynchus mykiss)Comp. Biochem. Physiol. C. Toxicol. Pharmacol.153(3)342-349(2011)
| Cas No. | 88-30-2 | SDF | |
| 别名 | 3-三氟甲基-4-硝基苯酚 | ||
| Canonical SMILES | OC(C=C1C(F)(F)F)=CC=C1[N+]([O-])=O | ||
| 分子式 | C7H4F3NO3 | 分子量 | 207.1 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 5 mg/ml | 储存条件 | -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 | 4.8286 mL | 24.1429 mL | 48.2859 mL |
| 5 mM | 0.9657 mL | 4.8286 mL | 9.6572 mL |
| 10 mM | 0.4829 mL | 2.4143 mL | 4.8286 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。
Control of invasive sea lampreys using the piscicides TFM and niclosamide: Toxicology, successes & future prospects
Aquat Toxicol 2019 Jun;211:235-252.PMID:30770146DOI:10.1016/j.aquatox.2018.12.012.
The invasion of the Laurentian Great Lakes of North America by sea lampreys (Petromyzon marinus) in the early 20th century contributed to the depletion of commercial, recreational and culturally important fish populations, devastating the economies of communities that relied on the fishery. Sea lamprey populations were subsequently controlled using an aggressive integrated pest-management program which employed barriers and traps to prevent sea lamprey from migrating to their spawning grounds and the use of the piscicides (lampricides) 3-trifluoromethyl-4-nitrophenol (TFM) and niclosamide to eliminate larval sea lampreys from their nursery streams. Although sea lampreys have not been eradicated from the Great Lakes, populations have been suppressed to less than 10% of their peak numbers in the mid-1900s. The ongoing use of lampricides provides the foundation for sea lamprey control in the Great Lakes, one of the most successful invasive species control programs in the world. Yet, significant gaps remain in our understanding of how lampricides are taken-up and handled by sea lampreys, how lampricides exert their toxic effects, and how they adversely affect non-target invertebrate and vertebrates species. In this review we examine what has been learned about the uptake, handling and elimination, and the mode of TFM and niclosamide toxicity in lampreys and in non-target animals, particularly in the last 10 years. It is now clear that the mode of TFM toxicity is the same in non-target fishes and lampreys, in which TFM interferes with oxidative phosphorylation by the mitochondria leading to decreased ATP production. Vulnerability to TFM is related to abiotic factors such as water pH and alkalinity, which we propose changes the relative amounts of the bioavailable un-ionized form of TFM in the gill microenvironment. Niclosamide, which is also a molluscicide used to control snails in areas prone to schistosomiasis infections of humans, also likely works by uncoupling oxidative phosphorylation, but less is known about other aspects of its toxicology. The effects of TFM include reductions in energy stores, particularly glycogen and high energy phosphagens. However, non-target fishes readily recover from sub-lethal TFM exposure as demonstrated by the rapid restoration of energy stores and clearance of TFM. Although both TFM and niclosamide are non-persistent in the environment and critical for sea lamprey control, increasing public and institutional concerns about pesticides in the environment makes it imperative to explore other means of sea lamprey control. Accordingly, we also address possible "next-generation" strategies of sea lamprey control including genetic tools such as RNA interference and CRISPR-Cas9 to impair critical physiological processes (e.g. reproduction, digestion, metamorphosis) in lamprey, and the use of green chemistry to develop more environmentally benign chemical methods of sea lamprey control.
New salts of teriflunomide (TFM) - Single crystal X-ray and solid state NMR investigation
Solid State Nucl Magn Reson 2022 Dec;122:101820.PMID:36067621DOI:10.1016/j.ssnmr.2022.101820.
New salts of teriflunomide TFM (drug approved for Multiple Sclerosis treatment) with inorganic counterions: lithium (TFM_Li), sodium (TFM_Na), potassium (TFM_K), rubidium (TFM_Rb), caesium (TFM_Cs) and ammonium (TFM_NH4) were prepared and investigated employing solid state NMR Spectroscopy, Powder X-ray Diffraction PXRD and Single Crystal X-ray Diffraction (SC XRD). Crystal and molecular structures of three salts: TFM_Na (CCDC: 2173257), TFM_Cs (CCDC: 2165288) and TFM_NH4 (CCDC: 2165281) were determined and deposited. Compared to the native TFM, for all crystalline salt structures, a conformational change of the teriflunomide molecule involving about 180-degree rotation of the end group, forming an intramolecular hydrogen bond N-H⋯O is observed. By applying a complementary multi-technique approach, employing 1D and 2D solid state MAS NMR techniques, single and powder X-ray diffraction measurements, as well as the DFT-based GIPAW calculations of NMR chemical shifts for TFM_Na and TFM_Cs allowed to propose structural features of TFM_Li for which it was not possible to obtain adequate material for single crystal X-Ray measurement.
Capability of the TFM Approach to Predict Fluidization of Cohesive Powders
Ind Eng Chem Res 2022 Mar 2;61(8):3186-3205.PMID:35264823DOI:10.1021/acs.iecr.1c04786.
The fluidization behavior of cohesive particles was investigated using an Euler-Euler approach. To do so, a two-fluid model (TFM) platform was developed to account for the cohesivity of particles. Specifically, the kinetic theory of granular flow (KTGF) was modified based on the solid rheology developed by Gu et al. J. Fluid Mech. 2019. The results of our simulations demonstrated that the modified TFM approach can successfully predict the formation of particle agglomerates and clusters in the fluidized bed, induced by the negative (tensile-dominant) pressure. The formation of such granules and clusters highly depended on the particle Bond number and the tensile pressure prefactor. To evaluate fluidization regimes, a set of simulations was conducted for a wide range of particle cohesivity (e.g., Bond number and tensile pressure prefactor) at two different fluidization numbers of 2 and 5. Our simulation results reveal the formation of four different regimes of fluidization for cohesive particles: (i) bubbling, (ii) bubbling-clustering, (iii) bubble-less fluidization, and (iv) stagnant bed. Comprehensive analysis of the shear-to-yield ratio reveals that the observed regime map is attributed to the competition between the shear stress and yield stress acting on the particles. The obtained regime map can be extended to incorporate the effect of dimensionless velocity and dimensionless diameter as a comprehensive fluidization chart for cohesive particles. Such fluidization charts can facilitate the design of fluidized beds by predicting the conditions under which the formation of particle agglomeration and clustering is likely in fluidized beds.
Tfm-AR modulates the effects of ApoE4 on cognition
J Neurochem 2008 Apr;105(1):63-7.PMID:18039320DOI:10.1111/j.1471-4159.2007.05092.x.
Female mice are more susceptible to apolipoprotein E (apoE4)-induced cognitive deficits than male mice. These deficits can be antagonized by stimulating androgen receptors (ARs). To determine the role of AR in the cognitive effects of apoE4, we backcrossed mutant mice with a naturally occurring defect in the AR [testicular feminization mutant (TFM)] onto the Apoe-/- background to eliminate mouse apoE gene resulting in non-functional AR, and crossed the TFM/Apoe-/- female mice with apoE4 transgenic male mice. We behaviorally compared Apoe-/-, apoE4, TFM, and TFM/apoE4 male mice. Apoe-/-, apoE4, and TFM mice showed hippocampus-dependent novel location recognition but TFM/apoE4 mice did not. In contrast, all groups showed hippocampus-independent novel object recognition. Hippocampus-dependent learning and memory were also assessed in the water maze. In the water maze probe trial following the second day of hidden platform training, Apoe-/- and apoE4 mice showed spatial memory retention, but TFM and TFM/ApoE4 mice did not. In the water maze, probe trial following the third day of hidden platform training, Apoe-/-, apoE4, and TFM/Apoe-/- mice showed spatial memory retention, but TFM mice did not. These data support an important role for AR in protecting against the detrimental effects of apoE4 on hippocampus-dependent learning and memory.
Niclosamide Is a Much More Potent Toxicant of Mitochondrial Respiration than TFM in the Invasive Sea Lamprey ( Petromyzon marinus)
Environ Sci Technol 2022 Apr 19;56(8):4970-4979.PMID:35363472DOI:10.1021/acs.est.1c07117.
Invasive sea lampreys in the Laurentian Great Lakes are controlled by applying TFM (3-trifluoromethyl-4-nitrophenol) and niclosamide to streams infested with their larvae. Both agents uncouple oxidative phosphorylation in the mitochondria, but TFM specifically targets lampreys, which have a lower capacity to detoxify the lampricide. Niclosamide lacks specificity and is more potent than TFM. However, its greater potency is poorly understood. We tested the hypothesis that niclosamide is a stronger uncoupler of mitochondrial oxidative phosphorylation than TFM by measuring oxygen consumption rates in isolated liver mitochondria exposed to physiologically relevant concentrations of TFM, niclosamide, or their mixture (100 TFM:1 niclosamide) at environmentally relevant temperatures (7, 13, and 25 °C). Niclosamide increased State 4 respiration and decreased the respiratory control ratio (RCR) at much lower concentrations than TFM. Calculations of the relative EC50 values, the amount of TFM or niclosamide required to decrease the RCR by 50%, indicated that niclosamide was 40-60 times more potent than TFM. Warmer temperature did not appear to decrease the sensitivity of mitochondria to niclosamide or TFM, as observed in the intact sea lamprey exposed to TFM in warmer waters. We conclude that the extreme sensitivity of mitochondria to niclosamide contributes to its greater in vivo toxicity in the whole animal.