Prodan
(Synonyms: N,N-二甲基-6-丙酰-2-萘胺) 目录号 : GC45680
A solvatochromic fluorescent probe
Cas No.:70504-01-7
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
Prodan is a solvatochromic fluorescent probe.1 It exhibits absorbance/emission maxima of 347/416 nm, respectively, in toluene, with both parameters increasing as solvent polarity increases. The emission maximum is also influenced by the phase state of membranes, such as in multilamellar vesicles containing 1,2-dipalmitoyl-sn-glycero-3-PC wherein the emission maximum of prodan shifts from approximately 440 nm in the gel phase to approximately 490 nm in the liquid crystalline phase.2 Prodan has been used to probe the microenvironmental conditions of biological and synthetic membranes.2,3
|1. Kucherak, O.A., Didier, P., MÉly, Y., et al. Fluorene analogues of prodan with superior fluorescence brightness and solvatochromism. J. Phys. Chem. Lett. 1(3), 616-620 (2010).|2. Parasassi, T., Krasnowska, E.K., Bagatolli, L., et al. Laurdan and prodan as polarity-sensitive fluorescent membrane probes. J. Fluoresc. 8(4), 365-373 (1998).|3. Mennucci, B., Caricato, M., Ingrosso, F., et al. How the environment controls absorption and fluorescence spectra of PRODAN: A quantum-mechanical study in homogeneous and heterogeneous media. J. Phys. Chem. B 112(2), 414-423 (2008).
| Cas No. | 70504-01-7 | SDF | |
| 别名 | N,N-二甲基-6-丙酰-2-萘胺 | ||
| Canonical SMILES | CCC(C1=CC2=C(C=C1)C=C(N(C)C)C=C2)=O | ||
| 分子式 | C15H17NO | 分子量 | 227.3 |
| 溶解度 | DMF: 10 mg/ml,DMF:PBS (pH 7.2) (1:2): 0.3 mg/ml,DMSO: 5 mg/ml,Ethanol: 1 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 | 4.3995 mL | 21.9974 mL | 43.9947 mL |
| 5 mM | 0.8799 mL | 4.3995 mL | 8.7989 mL |
| 10 mM | 0.4399 mL | 2.1997 mL | 4.3995 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。
Phase Imaging of Phosphatidylcholine Bilayer Membranes by Prodan Fluorescence
Membranes (Basel) 2022 Dec 2;12(12):1219.PMID:36557126DOI:10.3390/membranes12121219.
Prodan (6-propiponyl-2-(N,N-dimethylamino)naphthalene) is well known as a polarity-sensitive fluorescent probe and has a high capability of detecting structural changes occurring within phospholipid bilayer membranes. In this study, we carried out the fluorescence spectroscopic observation of bilayer phase behavior for a series of symmetric saturated diacylphosphatidylcholines (CnPCs) with different acyl-chain length n (n = 12-15 and 19-22) using Prodan as a membrane probe to confirm the availability of Prodan along with the previous results for the CnPC bilayer membranes (n = 16-18). The results were discussed by constructing spectral three-dimensional (3D) imaging plots for visualizing the change in bilayer phase states with temperature or pressure to verify the functionality of this 3D imaging plot. It was found that the Prodan fluorescence technique is applicable to the detection of the changes in the bilayer phase states of all CnPCs with a few exceptions. One of the most crucial exceptions was that Prodan cannot be used for the detection of the bilayer-gel state of the C21PC bilayer membrane. It was also found that it is only to the CnPC bilayer membranes with n = 15-18 that the 3D imaging plot is adequately and accurately applicable as a useful graphical tool for visually detecting the bilayer phase states. This is a disadvantageous feature of this technique brought about by the high sensitivity of Prodan as a membrane probe. Further detailed studies on the molecular behavior of Prodan will enable us to find a more useful way of utilizing this membrane probe.
Solvent-Dependent Excited-State Evolution of Prodan Dyes
J Phys Chem B 2021 Dec 30;125(51):13858-13867.PMID:34914398DOI:10.1021/acs.jpcb.1c09030.
Excited-state character and dynamics of two 6-(dimethylamino)-2-acylnaphthalene dyes (Prodan and Badan-SCH2CH2OH) were studied by picosecond time-resolved IR spectroscopy (TRIR) in solvents of different polarity and relaxation times: hexane, CD3OD, and glycerol-d8. In all these solvents, near-UV excitation initially produced the same S1(ππ*) excited state characterized by a broad TRIR signal. A very fast decay (3, ∼100 ps) followed in hexane, whereas conversion to a distinct IR spectrum with a ν(C═O) band downshifted by 76 cm-1 occurred in polar/H-bonding solvents, slowing down on going from CD3OD (1, 23 ps) to glycerol-d8 (5.5, 51, 330 ps). The final relaxed excited state was assigned as planar Me2N → C═O intramolecular charge transfer S1(ICT) by comparing experimental and TDDFT-calculated spectra. TRIR conversion kinetics are comparable to those of early stages of multiexponential fluorescence decay and dynamic fluorescence red-shift. This work presents a strong evidence that Prodan-type dyes undergo solvation-driven charge separation in their S1 state, which is responsible for the dynamic fluorescence Stokes shift observed in polar/H-bonding solvents. The time evolution of the optically prepared S1(ππ*) state to the S1(ICT) final state reflects environment relaxation and solvation dynamics. This finding rationalizes the widespread use of Prodan-type dyes as probes of environment dynamics and polarity.
Electric dipole moments of the fluorescent probes Prodan and Laurdan: experimental and theoretical evaluations
Biophys Rev 2014 Mar;6(1):63-74.PMID:28509963DOI:10.1007/s12551-013-0129-8.
Several experimental and theoretical approaches can be used for a comprehensive understanding of solvent effects on the electronic structure of solutes. In this review, we revisit the influence of solvents on the electronic structure of the fluorescent probes Prodan and Laurdan, focusing on their electric dipole moments. These biologically used probes were synthesized to be sensitive to the environment polarity. However, their solvent-dependent electronic structures are still a matter of discussion in the literature. The absorption and emission spectra of Prodan and Laurdan in different solvents indicate that the two probes have very similar electronic structures in both the ground and excited states. Theoretical calculations confirm that their electronic ground states are very much alike. In this review, we discuss the electric dipole moments of the ground and excited states calculated using the widely applied Lippert-Mataga equation, using both spherical and spheroid prolate cavities for the solute. The dimensions of the cavity were found to be crucial for the calculated dipole moments. These values are compared to those obtained by quantum mechanics calculations, considering Prodan in vacuum, in a polarizable continuum solvent, and using a hybrid quantum mechanics-molecular mechanics methodology. Based on the theoretical approaches it is evident that the Prodan dipole moment can change even in the absence of solute-solvent-specific interactions, which is not taken into consideration with the experimental Lippert-Mataga method. Moreover, in water, for electric dipole moment calculations, it is fundamental to consider hydrogen-bonded molecules.
Optical characterization of Prodan aggregates in water medium
Phys Chem Chem Phys 2013 Jul 28;15(28):11800-7.PMID:23756543DOI:10.1039/c3cp51776d.
The fluorescent probe Prodan (2-dimethylamino-6-propionylnaphthalene) has been widely used in biological systems, mainly due to the high sensitivity of its emission spectrum to the medium polarity. Though mostly used as a membrane probe, in lipid dispersions Prodan partitions in water, mainly in the presence of gel-phase bilayers. Here, optical properties of Prodan in aqueous medium are experimentally studied using absorption and emission spectroscopies, and compared with those of the probe in cyclohexane, where it is supposed to be very soluble. In parallel, theoretical calculations of the absorption spectrum of a monomer and aggregated Prodan in water were performed. Moreover, to understand Prodan-water and Prodan-Prodan interactions, solvation free energies of Prodan in water and in liquid Prodan were calculated. A light scattering profile underneath the optical absorption spectrum of Prodan in water clearly indicates the presence of aggregates at very low Prodan concentrations (0.9 μM). Experimental evidence of Prodan aggregation is theoretically supported by solvation free energy calculations, which demonstrate that Prodan molecules interact preferentially with other Prodan molecules than with water molecules. Theoretical calculations for electronic transition energies of monomers and aggregated Prodan in water show that a Prodan optical absorption band at 358 nm is related to the monomeric form of Prodan. This band saturates as Prodan concentration increases, indicating that aggregated Prodan prevails at higher concentrations. The relative increase in Prodan aggregated population is monitored by the increase in an absorption band at higher energies, at around 250 nm, and by the disappearance of a band at around 280 nm. Surprisingly, it was observed that the fluorescent emission spectrum of Prodan is not sensitive to probe aggregation up to around 15 μM. Hence, Prodan aggregation in water medium, even at very low concentrations, must be considered when using this fluorescent probe in biological systems, having in mind that its fluorescence spectrum is rather insensitive to aggregation.
Planar Chiral Analogues of Prodan Based on a [2.2]Paracyclophane Scaffold: Synthesis and Photophysical Studies
J Org Chem 2022 Jan 7;87(1):147-158.PMID:34908417DOI:10.1021/acs.joc.1c02071.
We describe the synthesis and photophysical characterization of differently substituted planar chiral analogues of Prodan based on a [2.2]paracyclophane scaffold. This experimental and theoretical study highlights that the (chir)optical properties of the new "phane" compounds, which incorporate an electron-withdrawing propionyl moiety and an electron-donating dimethylamino group at their para or pseudo-para positions, strongly depend on their substitution patterns. In particular, for this series of molecules, a more pronounced solvatochromism and clear chiroptical behaviors are observed when the two substituents are placed on the two rings of the pCp core in a non-"co-planar" arrangement (pseudo-para derivative). This observation may help design new pCp-based luminophores with finely tuned photophysical properties.