5-Nitro-1,10-phenanthroline
(Synonyms: 5-NP) 目录号 : GC682285-Nitro-1,10-phenanthroline (5-NP) 是一种 o-Phenanthroline 衍生物，是葡萄糖氧化酶 (GOX) 中介，具有抗结核菌活性。5-Nitro-1,10-phenanthroline 可作为氧化酶的氧化还原介质，适用于开发无试剂生物传感器和生物燃料电池。
Cas No.:4199-88-6
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
5-Nitro-1,10-phenanthroline (5-NP), is a o-Phenanthroline derivative, as a mediator of glucose oxidase (GOX) with antituberculous activity. 5-Nitro-1,10-phenanthroline can be applied as redox mediators for oxidases and is suitable for the development of reagent-less biosensors and biofuel cells[1][1].
5-Nitro-1,10-phenanthroline (25 μM; 24 h) kills naturally resistant intracellular bacteria by inducing autophagy in THP-1 macrophages[2].
5-Nitro-1,10-phenanthroline (1x, 5x, 20x or 50x MIC, MIC=0.78 μM; 1 h) also modulates the host machinery to kill intracellular pathogens by inhibiting mycolic acid biosynthesis of Mtb[2].
Cell Viability Assay[2]
| Cell Line: | Mtb H37Rv, M. bovis BCG and M. bovis BCG-5NP resistant strain |
| Concentration: | 0-12.5 μM |
| Incubation Time: | 24 hours |
| Result: | Inhibited pathogens with MIC99 values of 0.78 μM (Mtb H37Rv), 0.78 μM (M. bovis BCG), and >12.5 μM (M. bovis BCG-5NP), respectively. |
[1]. Oztekin Y, et al. 1,10-Phenanthroline derivatives as mediators for glucose oxidase. Biosens Bioelectron. 2010 Sep 15;26(1):267-70.
[2]. Kidwai S, et al. Dual Mechanism of Action of 5-Nitro-1,10-Phenanthroline against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2017 Oct 24;61(11):e00969-17.
| Cas No. | 4199-88-6 | SDF | Download SDF |
| 别名 | 5-NP | ||
| 分子式 | C12H7N3O2 | 分子量 | 225.2 |
| 溶解度 | 储存条件 | 4°C, protect from light, stored under nitrogen | |
| 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 | 4.4405 mL | 22.2025 mL | 44.405 mL |
| 5 mM | 0.8881 mL | 4.4405 mL | 8.881 mL |
| 10 mM | 0.444 mL | 2.2202 mL | 4.4405 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。
Di-μ-acetato-κO,O':O';κO:O,O'-bis-[(acetato-κO,O')bis-(5-nitro-1,10-phenanthroline-κN,N')cadmium]
Acta Crystallogr Sect E Struct Rep Online 2011 Sep 1;67(Pt 9):m1247.PMID:22058861DOI:10.1107/S1600536811032259.
In the binuclear title compound, [Cd(2)(C(2)H(3)O(2))(4)(C(12)H(7)N(3)O(2))(2)], the Cd(II) cations are linked by carboxyl-ate O atoms into a four-membered Cd(2)O(2) rhombic ring with a Cd⋯ Cd separation of 3.7515 (5) Å. Each Cd(II) atom is seven-coordinated by a bidentate 5-Nitro-1,10-phenanthroline (5-NO(2)-phen) ligand and two bidentate acetate anions, one of which also acts as a bridge linking the two Cd atoms. The crystal packing is stabilized by π-π inter-actions between the phen rings of neighboring mol-ecules, with centroid-centroid distances of 3.491 (2) (intra-molecular) and 3.598 (2) Å (inter-molecular).
Dual Mechanism of Action of 5-Nitro-1,10-phenanthroline against Mycobacterium tuberculosis
Antimicrob Agents Chemother 2017 Oct 24;61(11):e00969-17.PMID:28893784DOI:10.1128/AAC.00969-17.
New chemotherapeutic agents with novel mechanisms of action are urgently required to combat the challenge imposed by the emergence of drug-resistant mycobacteria. In this study, a phenotypic whole-cell screen identified 5-Nitro-1,10-phenanthroline (5NP) as a lead compound. 5NP-resistant isolates harbored mutations that were mapped to fbiB and were also resistant to the bicyclic nitroimidazole PA-824. Mechanistic studies confirmed that 5NP is activated in an F420-dependent manner, resulting in the formation of 1,10-phenanthroline and 1,10-phenanthrolin-5-amine as major metabolites in bacteria. Interestingly, 5NP also killed naturally resistant intracellular bacteria by inducing autophagy in macrophages. Structure-activity relationship studies revealed the essentiality of the nitro group for in vitro activity, and an analog, 3-methyl-6-nitro-1,10-phenanthroline, that had improved in vitro activity and in vivo efficacy in mice compared with that of 5NP was designed. These findings demonstrate that, in addition to a direct mechanism of action against Mycobacterium tuberculosis, 5NP also modulates the host machinery to kill intracellular pathogens.
Bis[μ-methyl-enebis(diphenyl-phosphine)]bis-[(5-Nitro-1,10-phenanthroline)silver(I)] bis-(hexa-fluoridoanti-monate)
Acta Crystallogr Sect E Struct Rep Online 2007 Dec 21;64(Pt 1):m264.PMID:21200600DOI:10.1107/S1600536807067013.
In the title compound, [Ag(2)(C(12)H(7)N(3)O(2))(2)(C(25)H(22)P(2))(2)](SbF(6))(2), the two Ag(I) atoms are bridged by the two methyl-enebis(diphenyl-phosphine) ligands and an eight-membered centrosymmetric metallacyclic ring is formed. The metal atom exhibits a distorted tetra-hedral coordination geometry, coordinated by two P atoms of the bridging ligands and two N atoms of the chelating 5-Nitro-1,10-phenanthroline ligand. The latter ligand shows minor disorder, adopting two orientations with site occupancy factors of 0.84 and 0.16.
1,10-Phenanthroline derivatives as mediators for glucose oxidase
Biosens Bioelectron 2010 Sep 15;26(1):267-70.PMID:20605713DOI:10.1016/j.bios.2010.05.005.
This study is focused on possible application of some 1,10-phenanthroline derivatives (PDs) in the development of biosensors and biofuel cells. Differently from some other studies, the PDs that were not involved into structures of metal complexes were investigated. Five PDs [1,10-phenanthroline monohydrate (PMH); 5-Nitro-1,10-phenanthroline (5NP); 5-amino-1,10-phenanthroline (5AP), 5-amino,6-nitro-1,10-phenanthroline (5A6NP) and 5,6-diamino-1,10-phenanthroline (56DAP)] were selected for this study. Bioelectrochemical responses of PDs and glucose oxidase (GOX)-modified graphite rod electrodes (GREs) were studied amperometrically and potentiometrically. The best redox mediators for GOX were found on PDs containing amino groups: 5AP and 56DAP. Amperometrical measurements have shown that 5NP derivative was also acting as a redox mediator but activity of 5NP was approximately four times lower than 5AP and three times lower than 56DAP. This study clearly illustrates that some PDs can be applied as redox mediators for oxidases and are suitable for the development of reagent-less biosensors and biofuel cells. Since amino groups can be very easily involved in the formation of chemical bounds, the amino-PDs are interesting compounds for the development of nanobiotechnological tools by bottom-up technique.
Structure and NIR-luminescence of ytterbium(III) beta-diketonate complexes with 5-Nitro-1,10-phenanthroline ancillary ligand: assessment of chain length and fluorination impact
Dalton Trans 2013 Oct 7;42(37):13516-26.PMID:23900403DOI:10.1039/c3dt51376a.
Seven new tris(β-diketonear-nate)ytterbium(III) complexes with the general formula [Yb(β-diketonate)3(5NO2phen)] (where the β-diketone is either 4,4,4-trifluoro-1-(2-naphthyl)-1,3-butanedione, 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione, 1,1,1-trifluoro-2,4-pentanedione, 1,1,1-trifluoro-5,5-dimethyl-2,4-hexanedione, 1,1,1,5,5,6,6,7,7,7-decafluoro-2,4-heptanedione, 2,4-hexanedione or 2,6-dimethyl-3,5-heptanedione, and 5NO2phen = 5-Nitro-1,10-phenanthroline) were synthesized and characterized by elemental analysis, attenuated total reflectance Fourier transform infrared spectroscopy and photoluminescence spectroscopy. Single crystal X-ray structures have been determined for three fluorinated complexes and ground state geometries of the other four complexes have been predicted using the Sparkle/PM6 model. These experimental structures and those designed by semi-empirical models reveal octacoordination around the Yb(3+) ion. Photoluminescence studies and lifetime measurements show that the increase in the fluorinated β-diketonate chain length is associated with a decrease in Yb(3+) luminescence intensity of the (2)F5/2→(2)F7/2 transition at around 980 nm and the (2)F5/2 excited state lifetime, while the ligand lifetime value remains almost unaffected. Finally, fluorination of the ligands is only advised when the complexes are to be used for co-doping with isostructural Er(3+) complexes for optical amplifiers, since it leads to a slight decrease in luminescence intensity for the same β-diketonate chain length.