1-Ethynylnaphthalene
(Synonyms: 1-乙炔萘；1-乙炔基萘) 目录号 : GC33073
1-Ethynylnaphthalene 是细胞色素 P450 1B1 的选择性抑制剂。
Cas No.:15727-65-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
1-Ethynylnaphthalene is a selective inhibitor of cytochrome P450 1B1.
1-Ethynylnaphthalene, selective inhibitor of cytochrome P450 IB1, does not affect 2-hydroxylation but inhibits 4-hydroxylation by 38%. At higher concentrations, 1-Ethynylnaphthalene inhibits 2-hydroxylation of 2-Hydroxylation of estradiol (E2) by ~30% and 4-hydroxylation of E2 by up to 80%[1].
[1]. Liehr JG, et al. 4-Hydroxylation of estradiol by human uterine myometrium and myoma microsomes: implications for the mechanism of uterine tumorigenesis. Proc Natl Acad Sci U S A. 1995 Sep 26;92(20):9220-4.
| Cas No. | 15727-65-8 | SDF | |
| 别名 | 1-乙炔萘；1-乙炔基萘 | ||
| Canonical SMILES | C#CC1=C2C=CC=CC2=CC=C1 | ||
| 分子式 | C12H8 | 分子量 | 152.19 |
| 溶解度 | DMSO : ≥ 125 mg/mL (821.34 mM) | 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 | 6.5707 mL | 32.8537 mL | 65.7073 mL |
| 5 mM | 1.3141 mL | 6.5707 mL | 13.1415 mL |
| 10 mM | 0.6571 mL | 3.2854 mL | 6.5707 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。
2-ethynylnaphthalene as a mechanism-based inactivator of the cytochrome P-450 catalyzed N-oxidation of 2-naphthylamine
Chem Res Toxicol 1989 Nov-Dec;2(6):367-74.PMID:2519725DOI:10.1021/tx00012a003.
Since the N-oxidation of several carcinogenic arylamines has been shown to be catalyzed preferentially by cytochrome P-450IA2 in several species, homologous ethynyl-substituted aromatic hydrocarbons, 2-ethynylnaphthalene, 1-Ethynylnaphthalene, and 2-ethynylfluorene, were synthesized and examined as potential mechanism-based inactivators of this monooxygenase. By use of 2-naphthylamine, whose N-oxidation was known to be selectively catalyzed by rat cytochrome P-450ISF-G (P-450IA2), and hepatic microsomes from isosafrole-treated rats, each of these ethynyl derivatives was found to be strongly inhibitory at concentrations of 1 and 10 microM. However, only inhibition by 2-ethynylnaphthalene was significantly enhanced by prior incubation with the microsomal system. The inactivation of 2-naphthylamine N-oxidation was found to be NADPH- and time-dependent and to follow pseudo-first-order kinetics, demonstrating that 2-ethynylnaphthalene is a potent mechanism-based inactivator of the enzymatic activity. The extrapolated kinactivation and KI were 0.23 min-1 and 8 microM, respectively. By use of 2-aminofluorene, whose N-oxidation was known to be catalyzed by both cytochromes P-450ISF-G and P-450 beta NF-B (P-450IA1), and the purified enzymes in a reconstituted system, both 2-ethynylnaphthalene and 1-Ethynylnaphthalene were found to be strongly inhibitory. However, 2-ethynylnaphthalene was a more potent inhibitor of the purified P-450ISF-G than of P-450 beta NF-B; and it was also found to be a more potent inhibitor of P-450ISF-G than was 1-Ethynylnaphthalene.(ABSTRACT TRUNCATED AT 250 WORDS)
Synthesis, Characterization, and Functionalization of 1-Boraphenalenes
Angew Chem Int Ed Engl 2018 Jul 2;57(27):8084-8088.PMID:29750391DOI:10.1002/anie.201803180.
1-Boraphenalenes have been synthesized by reaction of BBr3 with 1-(aryl-ethynyl)naphthalenes, 1-Ethynylnaphthalene, and 1-(pent-1-yn-1-yl)naphthalene and they can be selectively functionalized at boron or carbon to form bench-stable products. All of these 1-boraphenalenes have LUMOs localized on the planar C12 B core that are closely comparable in character to isoelectronic phenalenyl cations. In contrast to the comparable LUMOs, the aromatic stabilization of the C5 B ring in 1-boraphenalenes is dramatically lower than the C6 rings in phenalenyl cations. This is due to the occupied orbitals of π symmetry being less delocalised in the 1-boraphenalenes.
Synthesis and Characterizations of Macrocyclic Cr(III) and Co(III) 1-Ethynyl Naphthalene and 9-Ethynyl Anthracene Complexes: An Investigation of Structural and Spectroscopic Properties
Inorg Chem 2018 Feb 19;57(4):2249-2259.PMID:29411976DOI:10.1021/acs.inorgchem.7b03128.
Reported herein are the syntheses and structural and emission spectroscopic characterizations of new CrIII(HMC) and CoIII(cyclam) complexes bearing fluorophore alkynyl ligands, where HMC and cyclam are 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane and 1,4,8,11-tetraazacyclotetradecane, respectively. Two Cr(III) bis-1-ethynylnaphthalene (C2Np) complexes, trans-[Cr(HMC)(C2Np)2]Cl ([1]Cl) and cis-[Cr(HMC)(C2Np)2]Cl ([2]Cl), were prepared from the reactions between trans/cis-[Cr(HMC)Cl2]Cl and lithium 1-Ethynylnaphthalene (LiC2Np) in yields of 73 and 66%, respectively. Also investigated are CoIII(cyclam) complexes bearing both C2Np and C2ANT (ANT = 9-anthryl), namely [Co(cyclam)(C2Ar)Cl]Cl (Ar = ANT ([3]Cl), Np ([4]Cl)), [Co(cyclam)(C2Np)(NCCH3)](OTf)2 ([5](OTf)2), and [Co(cyclam)(C2Np)2]OTf ([6]OTf). Complexes [3]Cl (72%) and [4]Cl (67%) were prepared from the reaction between [Co(cyclam)Cl2]Cl and Me3SiC2ANT or Me3SiC2Np, respectively, in the presence of triethylamine. The reaction of [4]Cl with excess silver triflate in CH3CN yielded complex [5](OTf)2 (78%), which was reacted with HC2Np in the presence of triethylamine to form complex [6]OTf in 39% yield. Single crystal X-ray diffraction studies of [1]+, [3]+, [4]+, and [6]+ revealed a pseudo-octahedral geometry around the Cr(III) or Co(III) center with the tetraaza-macrocyclic ligand occupying the equatorial plane and the alkynyl- and/or chloro-ligand occupying the apical positions. The absorption spectra of complexes [1]+ and [2]+ display structured d-d bands between 400 and 550 nm, a feature that is absent in the d-d absorption of the Co(III) complexes [3]+-[6]+. Contrasting emission behaviors were observed: the Cr(III) complexes display metal-centered phosphorescence, while the Co(III) species exhibit ligand-based fluorescence. Time-delayed phosphorescence measurements revealed lifetimes of 447 and 97 μs for [1]+ and [2]+ at 77 K, respectively, and a room temperature lifetime of 218 μs for [1]+.
Inactivation of cytochrome P450s 2B1, 2B4, 2B6, and 2B11 by arylalkynes
Drug Metab Dispos 1997 Nov;25(11):1242-8.PMID:9351899doi
The time-dependent loss of the 7-ethoxy-4-trifluoromethylcoumarin (EFC) O-deethylase activity of rat P450 2B1, rabbit P450 2B4, or dog P450 2B11 by 1-Ethynylnaphthalene (1EN), 2-ethynylnaphthalene (2EN), 2-(1-propynyl)naphthalene (2PN), 1-ethynylanthracene (1EA), 2-ethynylanthracene, 2-ethynylphenanthrene, 3-ethynylphenanthrene, 9-ethynylphenanthrene (9EPh), 9-(1-propynyl)phenanthrene (9PPh), 4-ethynylpyrene (4EP), and 4-(1-propynyl)biphenyl (4PbP) was investigated. The rate constants for inactivation by the arylalkynes in descending order of effectiveness for the top five compounds were 9EPh>9PPh>1EN, 2EN, 2PN for 2B1, 9EPh>2EN>4EP>1EN, 1EA for 2B4, and 9EPh>1EA>4EP, 9PPh>2EN for 2B11. The size and the shape of the aromatic ring system and the placement of the alkyne functional group were important for inactivation. The most effective inactivator with all the isozymes was 9EPh. This compound also inactivated the EFC activity in microsomes from human lymphoblastoid cells expressing human P450 2B6. The specificity of 9EPh for the inhibition or inactivation of different P450 activities in microsomes from rats treated with various inducing agents was determined by measuring lidocaine, testosterone, p-nitrophenol, or erythromycin metabolism. The greatest effect was observed with the 2B-specific products from lidocaine and testosterone, whereas no effect was seen with p-nitrophenol or erythromycin. When the covalent binding of [3H]2EN to microsomal protein was analyzed by sodium dodecyl sulfate-polyacrylamide gel electrophoresis and autoradiography, a radiolabeled protein band that corresponds to 2B1 was observed in the lanes containing microsomes from rats treated with phenobarbital and, to a lesser extent, pyridine and isosafrole after incubation with NADPH. When these microsomes were incubated with [3H]9EPh or [3H]1EP, two NADPH-dependent bands were radiolabeled. One corresponded to 2B1/2 and the other to a protein of approximately 59 kDa, which was observed in the lanes from phenobarbital-treated male and female rats and pyridine-treated male rats. No radiolabeled bands were observed with [3H,14C]4PbP with any of the microsomes.
Suicide inhibitors of cytochrome P450 1A1 and P450 2B1
Biochem Pharmacol 1992 Aug 18;44(4):787-96.PMID:1510726DOI:10.1016/0006-2952(92)90417-h.
The inhibition of the P450 1A1 dependent de-ethylation of 7-ethoxyphenoxazone (7EPO) and the P450 2B1 dependent de-pentylation of 7-pentoxyphenoxazone (7PPO) by 1-Ethynylnaphthalene (1EN), 2-ethynylnaphthalene (2EN), 1-ethynylanthracene (1EA), 2-ethynylanthracene (2EA), 9-ethynylanthracene (9EA), 2-ethynylphenathrene (2EPh), 3-ethynylphenanthrene (3EPh), 9-ethynylphenanthrene (9EPh), 1-ethynylpyrene (1EP) and 2-ethynylpyrene (2EP) was studied in hepatic microsomal preparations from rats. Although all of the polycyclic aromatic acetylenes studied inhibited the dealkylation of 7EPO or 7PPO, only some of the acetylenes produced a mechanism-based irreversible inactivation (suicide inhibition) of the P450 dependent dealkylation of 7EPO or 7PPO. Of the molecules tested, only 1EP, 1EN, 2EN, 2EPh and 3EPh were effective suicide inhibitors of the P450 1A1 dependent de-ethylation of 7EPO and only 1EN, 2EN, 1EA and 9EPh were effective suicide inhibitors of the P450 2B1 dependent de-pentylation of 7PPO. In addition to the size and shape of the polycyclic aromatic ring system, placement of the carbon--carbon triple bond on the ring system was critical for suicide inhibition. In contrast to 1EP, 2EP was not a mechanism-based inhibitor of P450 1A1; 9EPh, but not 2EPh or 3EPh, was a suicide inhibitor of P450 2B1. None of the aryl acetylenes tested produced heme destruction under assay conditions that produced the suicide inhibition of the P450 dependent 7EPO or 7PPO dealkylation activities. Because a precise orientation of the terminal acetylene is required to produce suicide inhibition without heme destruction, acetylenic suicide inhibitors can potentially be used to differentiate between P450 isozymes and to establish some distinguishing geometric features of the active site of these isozymes.