Azobenzene

Azobenzene is a phototrigger that can be used to design and synthesize a variety of photoresponsive systems.Azobenzene is genotoxic and induces aggressive sarcomas of the spleen and other abdominal organs.

3'-Hydroxymethyl-4-(dimethylamino)azobenzene is a bioactive chemical.

SDMA p-Hydroxyazobenzene-p′-sulfonate is the p-hydroxyazobenzene-p′-sulfonate form of SDMA. It acts as an inhibitor of endogenous nitric oxide synthase (NO synthase) and serves as an activator of NF-κB, enhancing the expression of IL-6 and TNF-α. This compound remains stable in serum and plasma, making it a potential biomarker for liver and kidney dysfunction.

Diazobenzenesulfonic acid is a whiter or reddish crystalline acid derivative of sulfanilic acid. It is a desensitizer (inhibitor) of allosteric effect for myosin ATPase 13.

4-(Dimethylamino)-3'-fluoroazobenzene is a bioactive chemical.

PAD2-IN-2 (cis-isomer of 1) TFA is an inhibitor of protein arginine deiminase 2 (PAD2). This molecule features an azobenzene photoswitch, enabling the optical regulation of PAD activity. Additionally, PAD2-IN-2 TFA inhibits the citrullination of histone H3.

Thalidomide-Photoswitch3-NH2 hydrochloride is essential in creating PHOTACs, which are PROTACs activated by specific light wavelengths. These compounds become inactive in darkness and switch to an active cis isomer state under 390 nm irradiation, while wavelengths above 450 nm reverse this activation. This compound comprises a CRBN-recruiting ligand, an azobenzene photoswitchable crosslinker, and a pendant amine that interacts with an acid on the target warhead, and is used to synthesize PHOTAC-I-10 and PHOTAC-II-6.

QAQ dichloride is a photoswitchable compound that blocks voltage-gated Na v and K v channels. Its channel-blocking activity is observed in the trans form of the azobenzene photoswitch, while the cis form does not exhibit this effect. This compound is membrane-impermeant and selectively enters pain-sensing neurons expressing endogenous import channels. QAQ dichloride functions as a light-sensitive analgesic and provides a valuable tool for investigating signaling mechanisms involved in acute and chronic pain [1] [2].

Photoswitchable PAD inhibitor is a photoactivated protein arginine deiminase (PAD) inhibitor and a derivative of BB-Cl-amidine that contains an azobenzene photoswitch allowing optical control of PAD activity.1 Without photoactivation, it is a weak inhibitor of PAD2 (IC50 = >100 μM) and is less potent than BB-Cl-amidine in inhibiting citrulline production in vitro (kinact/KIs = 2,300, 600, 1,000, and 10,510 M-1min-1 for PAD1-4, respectively) and does not inhibit histone H3 citrullination in HEK293T cells overexpressing PAD2 when used at concentrations up to 100 μM. However, it can rapidly be photoactivated with UV-A radiation to the more active cis-isomer, which is an irreversible, competitive inhibitor of histone H3 citrullination with an IC50 value of 9.1 μM.References1. Mondal, S., Parelkar, S.S., Nagar, M., et al. Photochemical control of protein arginine deiminase (PAD) activity. ACS Chem. Biol. 13(4), 1057-1065 (2018). Photoswitchable PAD inhibitor is a photoactivated protein arginine deiminase (PAD) inhibitor and a derivative of BB-Cl-amidine that contains an azobenzene photoswitch allowing optical control of PAD activity.1 Without photoactivation, it is a weak inhibitor of PAD2 (IC50 = >100 μM) and is less potent than BB-Cl-amidine in inhibiting citrulline production in vitro (kinact/KIs = 2,300, 600, 1,000, and 10,510 M-1min-1 for PAD1-4, respectively) and does not inhibit histone H3 citrullination in HEK293T cells overexpressing PAD2 when used at concentrations up to 100 μM. However, it can rapidly be photoactivated with UV-A radiation to the more active cis-isomer, which is an irreversible, competitive inhibitor of histone H3 citrullination with an IC50 value of 9.1 μM. References1. Mondal, S., Parelkar, S.S., Nagar, M., et al. Photochemical control of protein arginine deiminase (PAD) activity. ACS Chem. Biol. 13(4), 1057-1065 (2018).

KIO-301 chloride, an azobenzene photoswitch compound, inhibits voltage-gated ion channels, such as hyperpolarisation-activated cyclic nucleotide-gated (HCN) channels and voltage-gated potassium channels, upon exposure to visible light [1].