1,3-Diphenylisobenzofuran
(Synonyms: 1,3-二苯基异苯并呋喃,DPBF) 目录号 : GC61705
1,3-Diphenylisobenzofuran(DPBF)是一种荧光探针，对单线态氧(1O2)的具有高特异性，可形成内过氧化物并分解成1,2-dibenzoylbenzene。1,3-Diphenylisobenzofuran可以检测活性氧(ROS)的生成。
Cas No.:5471-63-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
本方案仅提供一个指导，请根据您的具体需要进行修改。
1.制备染色液
(1)配置染料储存液：使用高质量无水DMSO配制浓度为10-20mM的储存液；
注意：未使用的储存液建议分装后在-20℃或-80°C避光保存，避免反复冻融。
(2)配置染料工作液：使用合适的缓冲液（如无血清细胞培养基或PBS，需预热）稀释储存液，配制浓度为10-20μM的染料工作液。
注意：请根据实际情况调整工作液浓度，现用现配。
2.细胞染色
(1)悬浮细胞：经1000g离心3-5分钟，弃去上清液，使用PBS或其他缓冲液清洗两次，每次5分钟；
(2)贴壁细胞：使用PBS或其他缓冲液清洗两次，加入胰酶消化细胞，消化完成后经1000g离心3-5min；
(3)加入染料工作溶液重悬细胞，将细胞在室温下避光孵育15-45min以允许染料渗透；
注意：
①建议染色过程中每隔5-10min重悬细胞一次，以便充分染色；
② 不同细胞最佳孵育时间不同，请根据具体实验需求自行摸索。
(4)孵育结束后，经1000g离心5分钟，去除染色液，加入PBS或其他缓冲液清洗2-3次，去除残留探针。
3.细胞贴壁染色
(1)在无菌盖玻片上培养贴壁细胞；
(2)从培养基中移走盖玻片，吸出过量的培养基，将盖玻片放在潮湿的环境中；
(3)从盖玻片的一角加入约100-150μL的染料工作液，轻轻晃动使染料均匀覆盖所有细胞；
(4) 将细胞在室温下避光孵育15-45min以允许染料渗透；
注意：不同细胞最佳孵育时间不同，请根据具体实验需求自行摸索；
(5)孵育结束后吸弃染料工作液，使用PBS或其他缓冲液清洗盖玻片2~3次。
4.荧光检测：通过荧光显微镜或流式细胞仪对染色结果进行观察。1,3-Diphenylisobenzofuran的最大激发光/发射光波长为495/523nm。
注意事项：
1）荧光染料均存在淬灭问题，请尽量注意避光，以减缓荧光淬灭。
2）为了您的安全和健康，请穿实验服并戴一次性手套操作。
1,3-Diphenylisobenzofuran (DPBF) is a fluorescent probe which possesses a highly specific reactivity towards singlet oxygen (1O2) forming an endoperoxide which decomposes to give 1,2-dibenzoylbenzene. 1,3-Diphenylisobenzofuran can detect the generation of reactive oxygen species (ROS)[1][2].
[1]. Weili Fan, et al. Calcium carbonate-methylene blue nanohybrids for photodynamic therapy and ultrasound imaging. Sci China Life Sci. 2018 Apr;61(4):483-491. [2]. P. Carloni, et al. On the use of 1,3-diphenylisobenzofuran (DPBF). Reactions with carbon and oxygen centered radicals in model and natural systems. Research on Chemical Intermediates volume 19, pages395-405(1993).
| Cas No. | 5471-63-6 | SDF | |
| 别名 | 1,3-二苯基异苯并呋喃,DPBF | ||
| Canonical SMILES | C1(C2=CC=CC=C2)=C3C=CC=CC3=C(C4=CC=CC=C4)O1 | ||
| 分子式 | C20H14O | 分子量 | 270.33 |
| 溶解度 | DMSO: 5.56 mg/mL (20.57 mM); Water: < 0.1 mg/mL (ultrasonic) (insoluble) | 储存条件 | Store at RT |
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.6992 mL | 18.4959 mL | 36.9918 mL |
| 5 mM | 0.7398 mL | 3.6992 mL | 7.3984 mL |
| 10 mM | 0.3699 mL | 1.8496 mL | 3.6992 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。
1,3-Diphenylisobenzofuran
Acta Crystallogr Sect E Struct Rep Online 2008 Mar 12;64(Pt 4):o686.PMID:21202078DOI:10.1107/S1600536808006016.
The structure of the title compound, 1,3-diphenyl-2-benzofuran, C(20)H(14)O, exhibits a distinct alternation of short [mean 1.361 (3) Å] and long [mean 1.431 (3) Å] C-C bonds around the benzofuran ring system, indicating a predominantly polyene character. Over 60 Diels-Alder adducts of this commercially available furan have been structurally characterized, but this is the first report of the structure of the parent compound.
1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission
Top Curr Chem (Cham) 2017 Sep 11;375(5):80.PMID:28895105DOI:10.1007/s41061-017-0162-3.
In this review we first provide an introductory description of the singlet fission phenomenon and then describe the ground and electronically excited states of the parent 1,3-Diphenylisobenzofuran chromophore (1) and about a dozen of its derivatives. A discussion of singlet fission in thin polycrystalline layers of these materials follows. The highest quantum yield of triplet formation by singlet fission, 200% at 80 K, is found in one of the two known crystal modification of the parent. In the other modification and in many derivatives, excimer formation competes successfully and triplet yields are low. A description of solution photophysics of covalent dimers is described in the next section. Triplet yields are very low, but interesting phenomena are uncovered. One is an observation of a separated-charges (charge-transfer) intermediate in highly polar solvents. The other is an observation of excitation isomerism in both singlet and triplet states, where in one isomer the excitation is delocalized over both halves of the covalent dimer, whereas in the other it is localized on one of the halves. In the last section we present the operation of a simple device illustrating the use of triplets generated by singlet fission for charge separation.
Chlorin e6-1,3-diphenylisobenzofuran polymer hybrid nanoparticles for singlet oxygen-detection photodynamic abaltion
Methods Appl Fluoresc 2021 Feb 13;9(2):025003.PMID:33524966DOI:10.1088/2050-6120/abe219.
A dual-functional nanosysterm is developed by means of Chlorin e6 (Ce6) as photosensitizer and 1,3-Diphenylisobenzofuran (DPBF) as fluorescent singlet oxygen (1O2) probe. Under 660 nm laser irradiation, Ce6 exhibites efficient 1O2 generation, and subsequently the production of 1O2 is assessed by the ratiometric fluorescence of PFO and DPBF under one-photon and two-photon excitation mode. The nanoparticles with excellent biocompatibility can be internalized into Hela cells and applied for tumor treatment. For intracellular PDT, the nanoparticles perform a high phototoxicity, while the PDT proccess can be evaluated in time by monitoring fluorescence signals of DPBF. This theranostic nanosysterm provides a facile strategy to fabricate 1O2-detection PDT, which can realize accurate and efficient photodynamic therapy based on singlet oxygen detection.
Covalent dimers of 1,3-Diphenylisobenzofuran for singlet fission: synthesis and electrochemistry
J Org Chem 2015 Jan 2;80(1):80-9.PMID:25384731DOI:10.1021/jo502004r.
The synthesis of covalent dimers in which two 1,3-Diphenylisobenzofuran units are connected through one phenyl substituent on each is reported. In three of the dimers, the subunits are linked directly, and in three others, they are linked via an alkane chain. A seventh new compound in which two 1,3-Diphenylisobenzofuran units share a phenyl substituent is also described. These materials are needed for investigations of the singlet fission process, which promises to increase the efficiency of solar cells. The electrochemical oxidation and reduction of the monomer, two previously known dimers, and the seven new compounds have been examined, and reversible redox potentials have been compared with results obtained from density functional theory. Although the overall agreement is satisfactory, some discrepancies are noted and discussed.
The development of 1,3-Diphenylisobenzofuran as a highly selective probe for the detection and quantitative determination of hydrogen peroxide
Free Radic Res 2017 Jan;51(1):38-46.PMID:27866421DOI:10.1080/10715762.2016.1262541.
1,3-Diphenylisobenzofuran (DPBF) has been developed as a selective probe for the detection and quantitative determination of hydrogen peroxide in samples containing different reactive nitrogen and oxygen species (RNOS). DPBF is a fluorescent probe which, for almost 20 years, was believed to react in a highly specific manner toward some reactive oxygen species (ROS) such as singlet oxygen and hydroxy, alkyloxy or alkylperoxy radicals. Under the action of these individuals DPBF has been rapidly transformed to 1,2-dibenzoylbenzene (DBB). In order to check if DPBF can act as a unique indicator of the total amount of different RNOS, as well as oxidative stress caused by an overproduction of these individuals, a series of experiments was carried out, in which DPBF reacted with peroxynitrite anion, superoxide anion, hydrogen peroxide, hypochlorite anion, and anions commonly present under biological conditions, namely nitrite and nitrate. In all cases, except for hydrogen peroxide, the product of the reaction is DBB. Only under the action of H2O2 9-hydroxyanthracen-10(9H)-one (oxanthrone) is formed. This product has been identified with the use of fluorescence spectroscopy, NMR spectroscopy, high performance liquid chromatography coupled with mass spectrometry, infrared spectroscopy, elemental analysis, and cyclic voltammetry (CV). A linear relationship was found between a decrease in the fluorescence intensity of DPBF and the concentration of hydrogen peroxide in the range of concentrations of 0.196-3.941 mM. DPBF responds to hydrogen peroxide in a very specific way with the limits of detection and quantitation of 88 and 122.8 μM, respectively. The kinetics of the reaction between DBBF and H2O2 was also studied.