Sulfabenzamide (N-Sulfanilylbenzamide)
(Synonyms: 苯甲酰磺胺; N-Sulfanilylbenzamide) 目录号 : GC33529
Sulfabenzamide (Sultrin, N-Sulfanilylbenzamide) is an antibacterial/antimicrobial which also exhibit their antitumor effects through multiple mechanisms including inhibition of membrane bound carbonic anhydrases, prevention of microtubule assembly, cell cycle arrest, and inhibition of angiogenesis.
Cas No.:127-71-9
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
Sulfabenzamide (Sultrin, N-Sulfanilylbenzamide) is an antibacterial/antimicrobial which also exhibit their antitumor effects through multiple mechanisms including inhibition of membrane bound carbonic anhydrases, prevention of microtubule assembly, cell cycle arrest, and inhibition of angiogenesis.
Sulfabenzamide inhibits the proliferation and increases Caspase-3 activity in T-47D cells. It dose not induce apoptosis but a minimal shift from G1 to S and G2/M phases of the cell cycle[1].
[1] Raziye MOHAMMADPOUR, et al. Journal of Cell and Molecular Biology. 2012, 10(1): 41-54.
| Cas No. | 127-71-9 | SDF | |
| 别名 | 苯甲酰磺胺; N-Sulfanilylbenzamide | ||
| Canonical SMILES | O=C(NS(=O)(C1=CC=C(N)C=C1)=O)C2=CC=CC=C2 | ||
| 分子式 | C13H12N2O3S | 分子量 | 276.31 |
| 溶解度 | DMSO : ≥ 2.9 mg/mL (10.50 mM) | 储存条件 | Store at 2-8°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 | 3.6191 mL | 18.0956 mL | 36.1912 mL |
| 5 mM | 0.7238 mL | 3.6191 mL | 7.2382 mL |
| 10 mM | 0.3619 mL | 1.8096 mL | 3.6191 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。
Acceptor substrate determines donor specificity of an aromatic prenyltransferase: expanding the biocatalytic potential of NphB
Appl Microbiol Biotechnol 2020 May;104(10):4383-4395.PMID:32189045DOI:10.1007/s00253-020-10529-8.
Aromatic prenyltransferases are known for their extensive promiscuity toward aromatic acceptor substrates and their ability to form various carbon-carbon and carbon-heteroatom bonds. Of particular interest among the prenyltransferases is NphB, whose ability to geranylate cannabinoid precursors has been utilized in several in vivo and in vitro systems. It has therefore been established that prenyltransferases can be utilized as biocatalysts for the generation of useful compounds. However, recent observations of non-native alkyl-donor promiscuity among prenyltransferases indicate the role of NphB in biocatalysis could be expanded beyond geranylation reactions. Therefore, the goal of this study was to elucidate the donor promiscuity of NphB using different acceptor substrates. Herein, we report distinct donor profiles between NphB-catalyzed reactions involving the known substrate 1,6-dihydroxynaphthalene and an FDA-approved drug molecule Sulfabenzamide. Furthermore, we report the first instance of regiospecific, NphB-catalyzed N-alkylation of Sulfabenzamide using a library of non-native alkyl-donors, indicating the biocatalytic potential of NphB as a late-stage diversification tool. KEY POINTS: • NphB can utilize the antibacterial drug Sulfabenzamide as an acceptor. • The donor profile of NphB changes dramatically with the choice of acceptor. • NphB performs a previously unknown regiospecific N-alkylation on Sulfabenzamide. • Prenyltransferases like NphB can be utilized as drug-alkylating biocatalysts.
A systematic study on hydrogen bond interactions in Sulfabenzamide: DFT calculations of the N-14, O-17, and H-2 NQR parameters
Biophys Chem 2009 Feb;139(2-3):116-22.PMID:19028005DOI:10.1016/j.bpc.2008.10.010.
A systematic computational study was carried out to characterize the hydrogen bond, HB, interactions of Sulfabenzamide crystal structure by DFT calculations of electric field gradient, EFG, tensors at the sites of 14N, 17O, and 2H nuclei. The computations were performed with the B3LYP and B3PW91 DFT methods and 6-311+G and 6-311++G* standard basis sets using the Gaussian 98 package. To perform the calculations, a hydrogen-bonded heptameric cluster of Sulfabenzamide was created by X-ray coordinates where the hydrogen atom positions were optimized and the EFG tensors were calculated for the target molecule. Additional optimization and EFG calculations were also performed for crystalline monomer and an isolated gas-phase Sulfabenzamide. The calculated EFG tensors were converted to the experimentally measurable nuclear quadrupole resonance, NQR, parameters: quadrupole coupling constant, C(Q), and asymmetry parameter, eta(Q). The results reveal that the geometrical and NQR parameters of the optimized isolated gas-phase and crystalline phase are different. In addition, the difference between the calculated NQR parameters of the monomer and the target molecule shows how much H-bonding interactions affect the EFG tensors of each nucleus. The evaluated NQR parameters reveal that due to the contribution of the target molecule to N-H...O and C-H...O hydrogen bond interactions, the EFG tensors at the sites of N1, O3 and H1 undergo significant changes from monomer to the target molecule in cluster. These features reveal the major role of N-H...O type intermolecular HBs in cluster model of Sulfabenzamide which the presence of these interactions can lead to polymorphism directly related to the drug activity and related properties.
Synthesis of sulfamethoxazole and Sulfabenzamide metal complexes; evaluation of their antibacterial activity
Eur J Med Chem 2019 Jun 1;171:364-371.PMID:30928708DOI:10.1016/j.ejmech.2019.03.002.
The present work describes the synthesis and spectroscopic characterization of ten different metal complexes of Sulfabenzamide and sulfamethoxazole as ligands (M-SBZ, M-SMZ). Spectroscopic methods such as 1H NMR, UV-Vis spectroscopy analysis, FTIR and XRD confirmed the coordination of both ligands to metals through the nitrogen and oxygen atoms of the sulfonamide group. Both Sulfabenzamide and sulfamethoxazole metal complexes were active against Gram-positive and negative bacterial strains. Sulfamethoxazole complexes showed their MIC values from 0.125 to 2.000 g ml-1 and Sulfabenzamide complexes exhibited related MIC values from 1.000 to 2.000 g ml-1. Finally Zn (II) sulfamethoxazole with an inexpensive and common metal displayed more activity than its free ligand drug.
Fluorescent probe study of sulfonamide binding to povidone
J Pharm Sci 1977 Aug;66(8):1157-9.PMID:894504DOI:10.1002/jps.2600660828.
The possibility of using a fluorescent probe technique for the study of drug-providone (I) interactions was investigated. 1-Anilino-8-naphthalenesulfonate (II) was used as the probe. Sulfanilamide, sulfacetamide, and Sulfabenzamide were used as the binding competitors. Both sulfacetamide and Sulfabenzamide decreased the fluorescence intensity of the I-II complex, while sulfanilamide increased the intensity. The fluorescence depression was greater with Sulfabenzamide than with sulfacetamide, indicating that the former is more strongly bound to povidone. Since Sulfabenzamide has a greater hydrophobic group (phenyl) than sulfacetamide (methyl), the binding of these sulfonamides to povidone is probably at least partially hydrophobic in nature. The enhanced fluorescence intensity of the I-II complex in the presence of sulfanilamide is believed to involve hydrogen bonding in which the sulfanilamide acts as an intermediary between I and II. Double reciprocal plots for the I-II and sulfonamide-I interactions were employed to obtain a binding constant of 3.2 X 10(4) M-1 for the I-II interaction. The association constants for sulfacetamide and Sulfabenzamide were calculated by means of the Klotz equation to be 13.4 and 56.8 M-1, respectively. The povidone molecules appear to have 1.28 binding sites for these compounds under the experimental conditions.
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection
Talanta 2004 Sep 8;64(1):87-100.PMID:18969572DOI:10.1016/j.talanta.2004.02.038.
A high performance liquid chromatography (HPLC) coupled to a mass spectrometer (MS) was used for a simultaneous determination of 16 sulfonamide compounds spiked in water, urine, milk, and bovine liver and kidney tissues. Supported liquid membrane (SLM) made up of 5% tri-n-octylphosphine oxide (TOPO) dissolved in hexyl amine was used as a sample clean-up and/or enrichment technique. The sulfonamides mixture was made up of 5-sulfaminouracil, sulfaguanidine, sulfamethoxazole, sulfamerazine, sulfamethizole, sulfamethazine (sulfadimidine), sulfacetamide, sulfapyridine, Sulfabenzamide, sulfamethoxypyridazine, sulfamonomethoxine, sulfadimethoxine sulfasalazine, sulfaquinoxaline, sulfadiazine, and sulfathiazole. Some of these compounds, such as, sulfaquinoxaline, sulfadiazine, Sulfabenzamide, sulfathiazole and sulfapyridine failed to be trapped efficiently by the same liquid membrane (5% TOPO in hexylamine). The detection limits (DL) obtained were 1.8ppb for sulfaguanidine and sulfamerazine and between 3.3 and 10ppb in bovine liver and kidney tissues for the other sulfonamides that were successfully enriched with SLM; 2.1ppb for sulfaguanidine and sulfamerazine and between 7.5 and 15ppb in cow's urine, whereas the DL values in milk were 12.4ppb for sulfaguanidine and sulfamerazine and between 16.8 and 24.3 for the other compounds that were successfully enriched by the membrane. Several factors affecting the extraction efficiency during SLM enrichment, such as donor pH, acceptor pH, enrichment time and the membrane solvent were studied.