electrophilic

Cysteine thiol probe (Methyl (4-bromobenzoyl)-L-cysteinate) is a chemoselective thiol probe for detection of electrophilic metabolites

α-Angelica lactone has cardiotonic activity, may exert their effects by providing an increased contraction-dependent calcium pool to be released upon systolic depolarization.

4-Hydroxycoumarin is a coumarin derivative and one of the versatile heterocyclic scaffolds with electrophilic and nucleophilic properties.

6-Bromo-2-naphthol is an electrophilic carbene intermediate.

2-tert-Butyl-1,4-benzoquinone (TBQ), an electrophilic metabolite of butylated hydroxyanisole (BHA), activates Nrf2 and S-arylates its negative regulator Keap1 in RAW264.7 cells.

DiaAlk is a clickable, electrophilic diazene probe which enables capture and site-centric proteomic analysis of oxidative post-translational modification (OxiPTM).

Stephacidin B is a fungal metabolite that has been found inA. ochraceus.1Dimeric stephacidin B is rapidly converted to a monomer, avrainvillamide ,in vitro.2Stephacidin B is cytotoxic to a variety of cancer cells, including testosterone-independent PC3 and -sensitive LNCaP prostate cancer cells (IC50s = 0.37 and 0.06 μM, respectively) and estradiol-independent SK-BR-3 and -sensitive MCF-7 breast cancer cells (IC50s = 0.32 and 0.27 μM, respectively).1It induces apoptosis in HepG2 and Huh7 hepatocellular carcinoma cells when used at a concentration of 4 μM.3 1.Qian-Cutrone, J., Huang, S., Shu, Y.-Z., et al.Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cellsJ. Am. Chem. Soc.124(49)14556-14557(2002) 2.Wulff, J.E., Herzon, S.B., Siegrist, R., et al.Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell cultureJ. Am. Chem. Soc.129(16)4898-4899(2007) 3.Hu, L., Zhang, T., Liu, D., et al.Notoamide-type alkaloid induced apoptosis and autophagy via a P38/JNK signaling pathway in hepatocellular carcinoma cellsRSC Adv.9(34)19855-19868(2019)

Pericosine A is a fungal metabolite that has been found inP. byssoidesand has anticancer activity.1It inhibits the growth of a variety of cancer cells, including breast, colon, lung, ovary, stomach, and prostate cell lines (GI50s = 0.05-24.55 μM) and increases survival in a P388 mouse xenograft model when administered at a dose of 25 mg/kg. Pericosine A inhibits EGFR by 40 to 70% when used at a concentration of 100 μg/ml. It also reacts with organosulfur compounds in skunk spray to form stable thioethers as odorless products.2 1.Yamada, T., Iritani, M., Ohishi, H., et al.Pericosines, antitumour metabolites from the sea hare-derived fungus Periconia byssoides. Structures and biological activitiesOrg. Biomol. Chem.5(24)3979-3986(2007) 2.Du, L., Munteanu, C., King, J.B., et al.An electrophilic natural product provides a safe and robust odor neutralization approach to counteract malodorous organosulfur metabolites encountered in skunk sprayJ. Nat. Prod.82(7)1989-1999(2019)

PF-4840154 is a potent, selective agonist of the rat and human TrpA1 channel, eliciting TrpA1-mediated nocifensive behavior in mouse, with EC50 values of 97 nM and 23 nM for [rTrpA1] and [hTrpA1], respectively.

DB008, a potent and selective PARP16 inhibitor, exhibits an IC50 value of 0.27 μM, incorporating an acrylamide electrophilic reagent. This membrane-permeable compound specifically targets PARP16.

MitoCur-1, a curcumin analogue, inhibits the mitochondrial antioxidative enzyme thioredoxin reductase 2 (TrxR2) and possesses electrophilic characteristics with mitochondrial-targeting capabilities. This compound specifically induces reactive oxygen species (ROS) generation, demonstrating antitumor efficacy [1].

AM841, a high-affinity electrophilic ligand, covalently interacts with a cysteine residue in helix six, thus activating the CB1 cannabinoid receptor. It diminishes forskolin-stimulated cAMP accumulation and slows gastrointestinal motility [1] [2].

MN551 is a potent inhibitor that targets the cysteine-directed electrophilic covalent activity essential for the function of SOCS2 within its CRL5 complex. This compound also acts as an E3 ligase mediator, facilitating PROTACs-induced selective protein degradation [1].

2,6-Dithiopurine (2,6-Dimercaptopurine) acts as a nucleophilic scavenger targeting electrophilic carcinogens. This compound effectively eliminates DNA adduct formation and impedes the initiation of carcinogenesis [1].

Cyprocide-B is activated by Cytochrome P450, which converts it into an electrophilic metabolite that selectively kills the nematode C. elegans. This compound holds promise for research into selective nematicidal agents.

2-bromomethyl benzothizaole is a derivative of benzothiazole. It is an intermediate and building block electrophilic reagent that has been used in the synthesis of many compounds such as 2-bromo-4-methyl-1,3-benzothiazole, a compound used in the synthesis of novel antifungal agents.

Biotin-PEAC5-maleimide hydrochloride is a biochemical detection reagent used in biotin-PEAC5-maleimide (BPM) labeling assays to evaluate the modification of protein thiols by electrophilic agents.