1,10-Phenanthroline (hydrate)
(Synonyms: 邻菲罗啉,1,10-Phenanthroline monohydrate) 目录号 : GC45978
A metal chelator and inhibitor of metalloproteases
Cas No.:5144-89-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
1,10-Phenanthrine is a metal chelator and inhibitor of metalloproteases.1,2,3 It inhibits zinc-dependent hydrolysis of Fa-Gly-Leu-NH2 by B. subtilis neutral protease and B. thermoproteolyticus thermolysin.1 1,10-Phenanthrine is fungistatic against P. verrucosa (MIC = 0.8 μg/ml) and inhibits zinc-induced P. verrucosa metallo-type peptidase activity in a concentration-dependent manner.2 It induces uncoupling of and inhibits egg production by adult S. mansoni worm pairs in vitro when used at concentrations ranging from 0.5 to 150 μM.3 1,10-Phenanthrine (20 mg/kg per day) reduces worm burden in a mouse model of S. mansoni infection.
|1. Feder, J., Garrett, L.R., and Kochavi, D. Studies on the inhibition of neutral proteases by 1,10-phenanthroline. Biochim. Biophys. Acta 235(2), 370-377 (1971).|2. Granato, M.Q., Massapust, P.d.A., Rozental, S., et al. 1,10-Phenanthroline inhibits the metallopeptidase secreted by Phialophora verrucosa and modulates its growth, morphology and differentiation. Mycopathologia 179(3-4), 231-242 (2014).|3. Day, T.A., and Chen, G.-Z. The metalloprotease inhibitor 1,10-phenanthroline affects Schistosoma mansoni motor activity, egg laying and viability. Parasitology 116(Pt. 4), 319-325 (1998).
| Cas No. | 5144-89-8 | SDF | |
| 别名 | 邻菲罗啉,1,10-Phenanthroline monohydrate | ||
| Canonical SMILES | C12=CC=C3C(N=CC=C3)=C1N=CC=C2.O | ||
| 分子式 | C12H8N2.H2O | 分子量 | 198.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:9): 0.1 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 | 5.0454 mL | 25.227 mL | 50.4541 mL |
| 5 mM | 1.0091 mL | 5.0454 mL | 10.0908 mL |
| 10 mM | 0.5045 mL | 2.5227 mL | 5.0454 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。
Novel cytotoxic 1,10-phenanthroline-triterpenoid amphiphiles with supramolecular characteristics capable of coordinating 64Cu(II) labels
Org Biomol Chem 2022 Oct 26;20(41):8157-8163.PMID:36222062DOI:10.1039/d2ob01172g.
1,10-Phenanthroline was decorated with triterpenoid-based substituents bearing additional spermine units to form amphiphilic molecules. The synthetic procedure designed for the new phenanthroline-triterpenoid amphiphiles is described in detail. Besides 1,10-Phenanthroline, all target structures bear 1,4-disubstituted 1,2,3-triazole rings. The target compounds self-assembled into either helical-like or sheet-like nanostructures, depending on the structure of the target molecule, either based on betulinic acid or oleanolic acid, and on the way of binding spermine subunits to the rest of the molecules. They also proved their ability to coordinate 64Cu(II) ions. Finally, the target compounds showed cytotoxicity that was partly dependent on the formation of nanostructures.
1,10-Phenanthroline-H2O2-KSCN-CuSO4-NaOH oscillating chemiluminescence system
Luminescence 2009 Mar-Apr;24(2):115-22.PMID:18785618DOI:10.1002/bio.1084.
In this paper, oscillating chemiluminescence (CL), 1,10-Phenanthroline H2O2-KSCN-CuSO4-NaOH system, was studied in a batch reactor. The system described is a novel, slowly damped oscillating CL system, generated by coupling the well-known Epstein-Orban, H2O2-KSCN-CuSO4-NaOH chemical oscillator reaction with the CL reaction involving the oxidation of 1,10-Phenanthroline by hydrogen peroxide, catalyzed by copper(II) in alkaline medium. In this system, the CL reaction acts as a detector or indicator system of the far-from-equilibrium dynamic system. Narrow and slightly asymmetric light pulses of 1.2 s half-width are emitted at 440 nm with an emitted light time of 200-1000 s, induction period of 3.5-357 s and oscillation period of 28-304 s depending on the reagent concentrations. In this report the effect of the concentration variation of components involved in the oscillating CL system on the induction period, the oscillation period and amplitude was investigated and the parameters were plotted with respect to reagent concentrations. Copper concentration showed a significant effect on the oscillation period. The possible mechanism for the oscillating CL reaction was also discussed.
μ-Acetato-μ-aqua-μ-hydroxido-bis[(1,10-Phenanthroline)copper(II)] dinitrate monohydrate
Acta Crystallogr C 2011 May;67(Pt 5):m130-3.PMID:21540527DOI:10.1107/S0108270111011048.
The triply bridged title dinuclear copper(II) compound, [Cu(2)(C(2)H(3)O(2))(OH)(C(12)H(8)N(2))(2)(H(2)O)](NO(3))(2)·H(2)O, (I), consists of a [Cu(2)(μ(2)-CH(3)COO)(μ(2)-OH)(phen)(2)(μ(2)-OH(2))](2+) cation (phen is 1,10-Phenanthroline), two uncoordinated nitrate anions and one water molecule. The title cation contains a distorted square-pyramidal arrangement around each metal centre with a CuN(2)O(3) chromophore. In the dinuclear unit, both Cu(II) ions are linked through a hydroxide bridge and a triatomic bridging carboxylate group, and at the axial positions through a water molecule. The phenanthroline groups in neighbouring dinuclear units interdigitate along the [010] direction, generating several π-π contacts which give rise to planar arrays parallel to (001). These are in turn connected by hydrogen bonds involving the aqua and hydroxide groups as donors with the nitrate anions as acceptors. Comparisons are made with isostructural compounds having similar cationic units but different counter-ions; the role of hydrogen bonding in the overall three-dimensional structure and its ultimate effect on the cell dimensions are discussed.
Structural analysis of metal chelation of the metalloproteinase thermolysin by 1,10-Phenanthroline
J Inorg Biochem 2021 Feb;215:111319.PMID:33310458DOI:10.1016/j.jinorgbio.2020.111319.
Metalloproteases and their inhibitors are important in numerous fundamental biochemical phenomena and medical applications. The heterocyclic organic compound, 1,10-Phenanthroline, forms a complex with transition metal ions and is a Zn2+-chelating metalloprotease inhibitor; however, the mechanism of 1,10-phenanthroline-based chelation inhibition has not been fully elucidated. This study aimed to understand the structural basis of zinc metalloproteinase inhibition by 1,10-Phenanthroline. Herein, the crystal structure of thermolysin was determined in the absence and presence of 1,10-Phenanthroline at 1.5 and 1.8 Å, respectively. In native thermolysin, Zn2+ at the active site is tetrahedrally coordinated by His142, His146, Glu166, and water molecule and contains three Ca2+ ions, which are involved in thermostability. In the crystal structure of 1,10-phenanthroline-treated thermolysin crystal, seven 1,10-Phenanthroline molecules were observed on the surface of thermolysin. These molecules are stabilized by π- π stacking interactions with aromatic amino acids (Phe63, Tyr66, Tyr110, His216, and Try251) or between the 1,10-phenanthrolines. Moreover, interactions with Ser5 and Arg101 were also observed. In this structure, Zn2+ at the active site was completely chelated, but no large conformational changes were observed in Zn2+ coordination with amino acid residues. Ca2+ at the Ca3 site exposed to the solvent was chelated by 1,10-Phenanthroline, resulting in a conformational change in the side chain of Asp56 and Gln61. Based on the surface structure, for 1,10-Phenanthroline to chelate a metal, it is important that the metal is exposed on the protein surface and that there is no steric hindrance impairing 1,10-Phenanthroline access by the amino acids around the metal.
Transition metal complexes and radical anion salts of 1,10-Phenanthroline derivatives annulated with a 1,2,5-tiadiazole and 1,2,5-tiadiazole 1,1-dioxide moiety: multidimensional crystal structures and various magnetic properties
Molecules 2014 Jan 7;19(1):609-40.PMID:24402196DOI:10.3390/molecules19010609.
Advances in the molecular variety and the elucidation of the physical properties of 1,10-Phenanthroline annulated with 1,2,5-thiadiazole and 1,2,5-thiadiazole 1,1-dioxide moieties have been achieved, and are described herein. A 1,2,5-thiadiazole compound, [1,2,5]thiadiazolo[3,4-f][1,10]phenanthroline (tdap), was used as a ligand to create multidimensional network structures based on S•••S and S•••N intermolecular interactions. A 1,2,5-thiadiazole 1,1-dioxide compound, [1,2,5] thiadiazolo[3,4-f][1,10]phenanthroline, 1,1-dioxide (tdapO2), was designed to create a stable radical anion, as well as good network structures. Single crystal X-ray structure analyses revealed that transition metal complexes of tdap, and radical anion salts of tdapO2 formed multidimensional network structures, as expected. Two kinds of tdap iron complexes, namely [Fe(tdap)2(NCS)2] and [Fe(tdap)2(NCS)2]•MeCN exhibited spin crossover transitions, and their transition temperatures showed a difference of 150 K, despite their similar molecular structures. Magnetic measurements for the tdapO2 radical anion salts revealed that the magnetic coupling constants between neighboring radical species vary from strongly antiferromagnetic (J=-320 K) to ferromagnetic (J=24 K), reflecting the differences in their π overlap motifs.