1,6-Diphenyl-1,3,5-hexatriene
(Synonyms: 1,6-二苯基-1,3,5-己三烯) 目录号 : GC45306
A fluorescent probe for lipid mono- and bilayers
Cas No.:1720-32-7
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
1,6-Diphenyl-1,3,5-hexatriene is a probe for lipid mono- and bilayers.1,2,3 It localizes to the hydrocarbon regions in lipid mono- and bilayers and displays excitation/emission maxima of 360/430 nm, respectively.1,2 1,6-Diphenyl-1,3,5-hexatriene has been used to characterize lipid membrane dynamics in vitro and ex vivo and in the determination of the critical micelle concentrations (CMCs) of anionic, cationic, uncharged, and zwitterionic detergents.1,2,3
References
1. Chattopadhyay, A., and London, E. Fluorimetric determination of critical micelle concentration avoiding interference from detergent charge. Anal. Biochem. 139(2), 408-412 (1984).
2. Tang, D., Wieb van der Meer, B., and Simon Chen, S.-Y. Evidence for a regular distribution of cholesterol in phospholipid bilayers from diphenylhexatriene fluorescence. Biophys J. 68(5), 1944-1951 (1995).
3. Cohen, B.M., and Zubenko, G.S. In vivo effects of psychotropic agents on the physical properties of cell membranes in the rat brain. Psychopharmacology (Berl) 86(3), 365-368 (1985).
| Cas No. | 1720-32-7 | SDF | |
| 别名 | 1,6-二苯基-1,3,5-己三烯 | ||
| Canonical SMILES | C1(/C=C/C=C/C=C/C2=CC=CC=C2)=CC=CC=C1 | ||
| 分子式 | C18H16 | 分子量 | 232.3 |
| 溶解度 | DMF: 0.2mg/mL,DMF:PBS (pH 7.2): 0.5mg/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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.3048 mL | 21.5239 mL | 43.0478 mL |
| 5 mM | 0.861 mL | 4.3048 mL | 8.6096 mL |
| 10 mM | 0.4305 mL | 2.1524 mL | 4.3048 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。
Phosphorylated 1,6-Diphenyl-1,3,5-hexatriene
Bioorg Med Chem Lett 2004 Mar 8;14(5):1075-8.PMID:14980638DOI:10.1016/j.bmcl.2004.01.005.
A lipophilic dye consisting of a (1E,3E,5E)-1,6-diphenyl-1,3,5-hexatriene (DPH) fluorophore attached to a phosphate diester was prepared, and its fluorescence behavior in different solvent systems and in a liposomal membrane bilayer was examined. The key step in the synthesis of the functionalized end of the dye is a Sonogashira coupling of protected iodophenol with propargyl alcohol; the remaining phenyl ring and double bonds of the all-trans polyene core arise from a Wittig reaction with trans-cinnamaldehyde. Like DPH itself, the emission intensity of its phosphorylated derivative is quenched in polar media.
The Fluorescent Dye 1,6-Diphenyl-1,3,5-hexatriene Binds to Amyloid Fibrils Formed by Human Amylin and Provides a New Probe of Amylin Amyloid Kinetics
Biochemistry 2021 Jun 29;60(25):1964-1970.PMID:34128641DOI:10.1021/acs.biochem.1c00328.
The fluorescent dye 1,6-Diphenyl-1,3,5-hexatriene (DPH) is widely used as a probe of membrane order. We show that DPH also interacts with amyloid fibrils formed by human amylin (h-amylin, also known as islet amyloid polypeptide) in solution, and this results in a 100-fold increase in DPH fluorescence for a sample of 20 μM h-amylin and 0.25 μM DPH. No increase in DPH fluorescence is observed with the non-amyloidogenic rat amylin or with freshly dissolved, nonfibrillar h-amylin. The time course of amyloid formation by amylin was followed by monitoring the fluorescence of added DPH as a function of time and was similar to that monitored by the standard fluorescent probe thioflavin-T. The inclusion of DPH in the buffer did not perturb the time course of amyloid formation under the conditions examined, and the time course was independent of the range of DPH concentrations tested (0.25-5 μM). The maximum final fluorescence intensity is observed at substoichiometric ratios of DPH to amylin. No significant increase in fluorescence was observed during the lag phase of amyloid formation, and the implications for the structure of amylin prefibril oligomers are discussed. h-Amylin contains three aromatic residues. A triple aromatic to leucine mutant forms amyloid, and DPH binds to the resulting fibrils, indicating that interactions with aromatic side chains are not required for DPH-amylin amyloid interactions. DPH may be especially useful for studies of mutant amylins and other polypeptides in which changes in charged residues might complicate interpretation of thioflavin-T fluorescence.
Some insights about 1,6-diphenyl-1,3,5-hexatriene-lipid supramolecular assemblies by steady-state fluorescence measurements
Appl Spectrosc 2007 Sep;61(9):963-9.PMID:17910793DOI:10.1366/000370207781745937.
1,6-Diphenyl-1,3,5-hexatriene (DPH) is the most widely proposed molecular probe for the post-column fluorescence derivatization of lipids after liquid chromatography separation. This kind of detection consists of a supramolecular combination of DPH and eluted lipids. The detection is optimally performed in a mainly aqueous environment (over 80% v/v) because the weak fluorescence of DPH in water is drastically enhanced upon formation of supramolecular assemblies with lipids. In the present study, and in order to obtain better spectroscopic insights into the nature of these supramolecular assemblies, two different lipids were tested, 1,2,3-tridodecanoylglycerol (LLL) as a model triglyceride (nonpolar lipid) and dimyristoylphosphatidylcholine (DMPC) as a model phosphatidylcholine (charged amphiphilic lipid). Stoichiometry and association constants were determined on the basis of the variation of fluorescence intensity in the presence of various concentrations of lipids. LLL(60)-DPH(2) and DMPC(200)-DPH(2) complexes were identified with association constants as high as K(2) = (5.8 +/- 0.5) x 10(13) M(-2) and (17.3 +/- 2.0) x 10(13) M(-2) for LLL and DMPC, respectively. The fluorescence intensity of DPH in the presence of LLL is greater than in the presence of DMPC. An attempt to characterize the insertion mode of DPH in the lipidic supramolecular assemblies is also made.
Coumarin 6 and 1,6-Diphenyl-1,3,5-hexatriene (DPH) as fluorescent probes to monitor protein aggregation
Analyst 2011 May 21;136(10):2161-7.PMID:21445407DOI:10.1039/c0an00829j.
We report the use of Coumarin 6 and 1,6-Diphenyl-1,3,5-hexatriene (DPH) for the identification of protein aggregates for the first time. The two dyes can be used at very low (nanomolar) concentrations and do not interfere with the aggregation process, as is reported for other commonly used fluorescent protein probes. In the presence of protein aggregates, their quantum yields are significantly high. DPH is able to recognize both amorphous and fibrillar aggregates but cannot distinguish between them. Coumarin 6 can distinguish between both types of aggregates. It also exhibits the characteristic sigmoidal curve of amyloid formation, with higher sensitivity for detection of fibrillation than the conventionally used Thioflavin T.
Developmental changes in synaptic membrane fluidity: a comparison of 1,6-Diphenyl-1,3,5-hexatriene (DPH) and 1-[4-(trimethylamino)phenyl]-6-phenyl-1,3,5-hexatriene (TMA-DPH)
Brain Res 1984 May;316(1):113-20.PMID:6733531DOI:10.1016/0165-3806(84)90014-2.
Cortical synaptic plasma membranes were prepared from rats 3, 7, 10, 14, 21, 28 and 120 days of age. Developmental changes in the fluidity of these membranes were assessed using fluorescence polarization techniques. 1,6-Diphenyl-1,3,5-hexatriene (DPH), a probe of the membrane interior, showed a marked developmental increase in polarization, suggesting a developmental decrease in fluidity. The magnitude of the change from day 3 to the adult was the equivalent of lowering the temperature 7 degrees C. The developmental change in DPH polarization was maintained in liposomes (multilamellar vesicles) prepared from membrane total lipid extracts. In contrast to DPH, 1-[4-(trimethylamino)phenyl]6-phenyl-1,3,5-hexatriene (TMA-DPH), a probe of the membrane surface reported no significant developmental effect on polarization for intact membranes; however, TMA-DPH did report a significant increase in polarization for the total lipid extract liposomes. For the intact membranes, both cis- and trans-parinarate, fluorescent probes of the mid-region of the acyl chains, reported significant developmental increases in polarization. The role of gangliosides in the developmental regulation of fluidity was examined. Gangliosides did not appear to play a role in the developmental changes, but they do have a significant effect (increased polarization) on the membrane surface as reported by TMA-DPH. Fluorescence lifetime and heterogeneity analyses were performed for DPH. There was a small but significant increase in probe lifetime during development. Thus, polarization measurements alone underestimated the increases in membrane order. In an attempt to amplify the differences in membrane organization between the developing and adult membranes, we examined the effects of the membrane perturbant ethanol, on DPH polarization at the different ages. No developmental effect on the ethanol-induced fluidization of synaptic membranes was observed.