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Chemical Structure| 1007-16-5 Chemical Structure| 1007-16-5

Structure of 1007-16-5

Chemical Structure| 1007-16-5

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CAS No.: 1007-16-5

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Senevirathne, Prasadini ; Sterling, Alyssa ; Anne Refaei, Mary ; Mokhtarpour, Nazanin ; Gutierrez-Rivera, Laura ; Garcia, Joshua , et al.

Abstract: NADPH oxidases (NOXs) are newly identified enzymes that generate intracellular reactive oxygen species (ROS) in skin cells. Recent studies demonstrated that NOX1 holoenzyme is expressed in human keratinocytes and melanocytes, which are implicated in skin photo-carcinogenesis due to the high amounts of ROS produced. Holoenzyme activation requires a ternary complex comprised of NOX1, cytochrome B alpha chain (CYBA), and cytoplasmic NADPH Oxidase Organizer 1 (NOXO1) to properly form. By inhibiting this assembly process, an opportunity for reducing the production of catalytic ROS is possible, especially during high ROS conditions that occur under prolonged UV exposure. We designed a series of small mols. and evaluated their inhibitory effects on NOXO2 using in-silico docking methods in the 1WLP crystal structure. We show that the NOX_inh_5 inhibitor was successful in a variety of experiments using primary skin models from various skin tones. NOX_inh_5 proved to be non-cytotoxic while also improving the viability of primary human skin primary cells under UV exposure. Biophys. studies with NOX_inh_5 using an Isothermal calorimetric (ITC) binding and heteronuclear single quantum coherence (HSQC-NMR) exhibited inhibition of complex formation between NOXO2 and CYBA. Authentic human skin explants, treated with and without NOX_inh_5 and UV exposure, decreased p53 stabilization and decreased UV-induced DNA damage as quantified through cyclobutane dimer formation.

Keywords: Reactive oxygen species ; Apocynin ; UV ; Melanoma ; Sunscreen ; NOXO1 ; CYBA

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Senevirathne, Priyangika Prasadini ;

Abstract: Reactive oxygen species are a group of highly reactive oxygen-containing entities that are important at a cellular level for multiple biological processes. Low concentrations of ROS can be beneficial as powerful signaling molecules in those biological processes, although excessive concentrations can promote high levels of DNA damage and a variety of diseases such as skin cancer. A newly identified intracellular ROS production source in skin cells is NADPH oxidases. Out of the NOX enzyme family, the NOX1 holoenzyme is most abundantly expressed in the human keratinocyte cells. UV radiation can trigger the activation of NOX1 isoforms which stimulate the assembling of member CYBA and the cytoplasmic protein NOXO1. Inhibition of these enzymes represents a catalytic approach toward reducing ROS for the prevention of ROS inducible diseases. Key disease states include melanoma induced by UV exposure. The first half of the dissertation focuses on investigating new small molecule inhibitors of a key NOX1 holoenzyme to address these challenges. We designed a series of molecules by optimizing the structure of diapocynin and evaluated by in-silico docking methods to determine the binding affinity with NOXO1 cytoplasmic protein (1WLP crystal structure). And have synthesized the series of target molecules for the structure-activity relationship studies. In the first section of the project, we discovered that inhibitor NOX_inh_5 was not cytotoxic, but instead improved the viability of human primary cells from UV exposure, decreased the cellular stress in human skin through the p53 pathway, and reduced the UV-induced DNA damage as monitored by quantification of cyclobutane dimer formation after UV exposure. Then, we characterized the inhibition potential of NOX_inh_5 by using an Isothermal calorimetric (ITC) binding assay and heteronuclear single quantum coherence (HSQC) technique and revealed that the candidate iii molecule can prevent the complex formation of NOXO1 and CYBA membrane protein. In the second section of the project, we did a structure-activity relationship study for the NOX_inh_5 small molecule to optimize the biological characteristics. The last section of the dissertation discussed the development of ROS sensible prodrug to combat the opioid overdose crisis. Here we used oxidative stress conditions caused by opioid overdose to activate the prodrug. Even though opioid antagonist naloxone has a high affinity to bind with opioid receptors to block opioid-induced activation, it is metabolically unstable and has a short half-life of around 33 min. We developed a peroxide-induced prodrug to overcome this issue that can release a steady stream of naloxone. This allows the concentration of naloxone to remain high for longer periods.

Alternative Products

Product Details of [ 1007-16-5 ]

CAS No. :1007-16-5
Formula : C7H4BrFO2
M.W : 219.01
SMILES Code : O=C(O)C1=CC=C(F)C(Br)=C1
MDL No. :MFCD00042463

Safety of [ 1007-16-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1007-16-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1007-16-5 ]

[ 1007-16-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1007-16-5 ]
  • [ 74-88-4 ]
  • [ 206551-41-9 ]
YieldReaction ConditionsOperation in experiment
89.5% With potassium carbonate; In tert-butyl methyl ether; N,N-dimethyl-formamide; at 20℃; for 16h; To a 100 mL round bottom flask was added 3-bromo-2-fluorobenzoic acid (5.00 g, 22.8 mmol, Oakwood), potassium carbonate (3.17 g, 22.9 mmol), and DMF (30 mL).Iodomethane, 2 M in MTBE (11.6 ml, 23.2 mmol) was added and the reaction mixture was stirred at RT for 16 hours. The reaction was filtered and the filtrate concentrated was in vacuo. The resulting brown crude residue was taken up with EtOAc and again filtered and concentrated to give methyl 3-bromo-2-fluorobenzoate (4.76 g, 20.4 mmol, 89.5percent yield), as a brown syrup that was used in the Step 2 without further purification.
  • 2
  • [ 1007-16-5 ]
  • [ 75-65-0 ]
  • [ 375368-94-8 ]
YieldReaction ConditionsOperation in experiment
Exam ple 1E: Com pound 1OT7Step 1- Add carbonyi diimtcfazoie (3.68 g, 227 mmol) to a mixture of 3-bromo-4-fluoro benzoic acid 1e1 (2.51 g, 115 mmoi) in DMF (25 mL} and stir at RT for about 1 ft. Cool the reaction to CfC and add t-BuOH (5,7 ml, 59,4 mmol). Then add DBU (1.9 mL, 12,8 mmol) dropwise. Allow the mixture to warm to RT and stir for about 21 ft, Dilute the mixture with t-BME and wash successively with 10% titrie acid (aqueous) and saturated NaHCO^ (aqueous). Dry over MgSO4, filter and evaporate the votatiies to obtain 1e2.
  • 3
  • [ 1007-16-5 ]
  • [ 369-26-6 ]
 

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