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Identification of a Noxo1 inhibitor by addition of a polyethylene glycol chain
Mokhtarpour, Nazanin ; Sterling, Alyssa ; Garcia, Joshua J. , et al. Bioorgan. Med. Chem.,2023,85,117274. DOI: 10.1016/j.bmc.2023.117274 PubMed ID: 37031566
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Abstract: Reactive oxygen species (ROS) are a heterogeneous group of highly reactive ions and mols. derived from mol. oxygen (O2) which can cause DNA damage and lead to skin cancer. NADPH oxidase 1 (Nox1) is a major producer of ROS in the skin upon exposure to UV light. Functionally, Nox1 forms a holoenzyme complex that generates two superoxide mols. and reduces NADPH. The signaling activation occurs when the organizer subunit Noxo1 translocates to the plasma membrane bringing a cytochrome P 450, through interaction with Cyba. We propose to design inhibitors that prevent Cyba-Noxo1 binding as a topical application to reduce UV-generated ROS in human skin cells. Design started from an apocynin backbone structure to generate a small mol. to serve as an anchor point. The initial compound was then modified by addition of a polyethylene glycol linked biotin. Both inhibitors were found to be non-toxic in human keratinocyte cells. Further in vitro experiments using isothermal calorimetric binding quantification showed the modified biotinylated compound bound Noxo1 peptide with a KD of 2 nM. Both using isothermal calorimetric binding and MALDI (TOF) MS showed that binding of a Cyba peptide to Noxo1 was blocked. In vivo experiments were performed using donated skin explants with topical application of the two inhibitors. Experiments show that UV light exposure of with the lead compound was able to reduce the amount of cyclobutene pyrimidine dimers in DNA, a mol. known to lead to carcinogenesis. Further synthesis showed that the polyethylene glycol but not the biotin was essential for inhibition.
Keywords: Reactive oxygen species ; Apocynin ; UV ; Noxo1 ; Cyba ; Cyclobutane pyrimidine dimer ; CPD ; UV protection
Purchased from AmBeed: 615-43-0 ; 58-85-5 ; 351422-73-6 ; 158407-04-6 ; 103-67-3 ; 103-67-3
CAS No. : | 103-67-3 | MDL No. : | |
Formula : | C8H11N | Boiling Point : | - |
Linear Structure Formula : | C6H5CH2NH(CH3) | InChI Key : | RIWRFSMVIUAEBX-UHFFFAOYSA-N |
M.W : | 121.18 | Pubchem ID : | 7669 |
Synonyms : |
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Chemical Name : | N-Methyl-1-phenylmethanamine |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P210-P260-P280-P305+P351+P338-P310 | UN#: | 2735 |
Hazard Statements: | H227-H314-H317-H334 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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.
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