a-naphthoquinone

1,4-Naphthoquinone (P-Naphthoquinone) was used as a potential inhibitor of monoamine oxidase and DNA topoisomerase activities[2]. It was also used to inhibit the acetyltransferase activity[1].

Menadione (Vitamin K3) is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.

Quinoclamine is a naphthoquinone derivative and is an NF-κB inhibitor.

Plumbagin (Plumbaein) is a yellow dye, formally derived from naphthoquinone. It is named after the plant genus Plumbago, from which it was originally isolated. It is also commonly found in the carnivorous plant genera Drosera and Nepenthes. It is also a component of the black walnut drupe.

Lawsone (Hennotannic acid) (2-hydroxy-1,4-naphthoquinone), also known as hennotannic acid, is a red-orange dye present in the leaves of the henna plant (Lawsonia inermis) as well as in the flower of water hyacinth (Eichhornia crassipes).

2-Hydroxyanthraquinone is an anthraquinone that has been found inSpermacoce latifoliaand has antibacterial and estrogenic activities.1,2It is active againstB. subtilisandB. cereus(MICs = 1.9 and 62.5 μg/ml, respectively).12-Hydroxyanthraquinone (19 μM) induces estrogen receptor α (ERα) activation in a yeast two-hybrid assay.2 1.Luo, Y., Shen, H.-Y., Shen, Q.-X., et al.A new anthraquinone and a new naphthoquinone from the whole plant of Spermacoce latifoliJ. Asian Nat. Prod. Res.19(9)869-876(2017) 2.Kurihara, R., Shiraishi, F., Tanaka, N., et al.Presence and estrogenicity of anthracene derivatives in coastal Japanese watersEnviron. Toxicol. Chem.24(8)1984-1993(2005)

Juglone (Regianin) is a natural naphthoquinone found in the black walnut (J. nigra) and other plants in the Juglandaceae family. Juglone also irreversibly inhibits peptidyl-prolyl cis/trans isomerases of the parvulin family, including human Pin1, yeast Ess1/Ptf1, and E. coli parvulin (Ki = 55.9 nM). Juglone also blocks transcription by RNA polymerases I, II, and III (IC50s = 2-7 μM) and attenuates kidney fibrosis in rats treated with unilateral ureteral obstruction, both through Pin1-independent mechanisms.

2-Chloronaphthoquinone (2-Chloro-1,4-naphthoquinone) is a substituted naphthoquinone which is used as an insecticide and acaricide.

FUT8-IN-1 (Compound 37) is an inhibitor of α-1,6-fucosyltransferase (FUT8), with a dissociation constant (KD) of 49 nM and an IC50 around 50 µM. In the presence of FUT8, FUT8-IN-1 forms a highly active naphthoquinone imine intermediate, thereby inhibiting FUT8's enzymatic activity.

6-Ethoxyethyl-5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone is a naphthoquinone compound known to cause withering of larch branches and inhibit the germination and growth of lettuce seeds. At a concentration of 100 ppm, it completely inhibits the growth of hypocotyls and roots, and at 50 ppm, it suppresses over 95%.

MEK Inhibitor II (2-Chloro-3-(N-succinimidyl)-1,4-naphthoquinone) is a selective MEK1 inhibitor (IC50=0.38 μM) that inhibits tubulin polymerization in Trypanosoma cruzi (IC50=6 μM) and exhibits inhibitory activity against trypanosomes (IC50=2.77 μM).

A 80915A is A semi-naphthoquinone antibiotic from Streptomyces aculeolatus. It is a potent inhibitor of gastric (H(+)-K+)-ATPase. Inhibition by A80915A is dependent on the conformation of gastric (H(+)-K+)-ATPase, potassium slows the rate of inhibition by

(Rac)-Shikonin (Anchusin) is a natural red naphthoquinone pigment, has antimicrobial, anti-tumor, and anti-inflammatory effects; a purified shikonin preparation is widely used for the production of medicinals, cosmetics, and some food products; shikonin also enters into the antiinflammatory ointment and cream compositions used for the treatment of burns. It can suppress the cell viability, adhesion, invasion and migratory ability of MGC-803 cells through TLR2- or NF-κB-mediated pathway.

AK-135 is a derivative of 1,4-naphthoquinone (Menadione). AK-135 has been shown to restore the electron flow in defective respiratory chain (hypoxia or rotenone) systems more effectively than Menadione.

Methylspinazarin is a naphthoquinone bacterial metabolite that has been found in Streptomyces and is an inhibitor of catechol O-methyltransferase (COMT; IC50 = 0.8 μg/ml).1 It is selective for COMT over tyrosine hydroxylase, DOPA decarboxylase, and dopamine-β-hydroxylase at 100 μg/ml. Methylspinazarin decreases blood pressure in spontaneously hypertensive rats when administered at a dose of 50 mg/kg. |1. Chimura, H., Sawa, T., Takita, T., et al. Methylspinazarin and dihydromethylspinazarin, gatechol-O-methyl transerfase inhibitors produced by Streptomyces. J. Antibiot. 26(2), 112-114 (1973).

CAY10763 is a dual inhibitor of indolamine 2,3-dioxygenase 1 (IDO1; IC50= 46 nM) and STAT3 activation.1It binds to STAT3 (Kd= 530 nM) and selectively reduces the levels of STAT3 phosphorylated at the tyrosine in position 705 (STAT3Y705) over phosphorylated STAT3S727, STAT1, and STAT5 in SKOV3 cells when used at a concentration of 500 nM. It also inhibits STAT3 nuclear translocation in SKOV3 cells. CAY10763 is cytotoxic to HCT116, SKOV3, A549, and HepG2 cancer cells (IC50s = 37, 28, 33, and 12 nM, respectively). It reduces tumor growth in B16/F10 mouse melanoma and HepG2 mouse xenograft models when administered at doses of 100 and 10 mg/kg, respectively. 1.Huang, R., Jing, X., Huang, X., et al.Bifunctional naphthoquinone aromatic amide-oxime derivatives exert combined immunotherapeutic and antitumor effects through simultaneous targeting of indoleamine-2,3-dioxygenase and signal transducer and activator of transcription 3J. Med. Chem.63(4)1544-1563(2020)

(-)-Alkannin (Shikonin) is a natural red naphthoquinone pigment, has antimicrobial, anti-tumor, and anti-inflammatory effects; a purified shikonin preparation is widely used for the production of medicinals, cosmetics, and some food products; shikonin also enters into the antiinflammatory ointment and cream compositions used for the treatment of burns. It can suppress the cell viability, adhesion, invasion and migratory ability of MGC-803 cells through TLR2- or NF-κB-mediated pathway.

DMNQ is a 1,4-naphthoquinone that acts as a redox-cycling agent, typically increasing intracellular superoxide and hydrogen peroxide formation.DMNQ increases ROS generation

Beta-Acetoxyisovalerylshikonin is a naphthoquinone derivative extracted from Arnebia euchroma.

2, 3-Dichloro-1, 4-naphthoquinone is an inhibitor of Itch, a HECT domain-E3 ligase. It is also used in pesticide formulations.

2-(Cyclohexylmethyl)-Plumbagin, a naphthoquinone derivative, exhibits selective cytotoxicity towards PANC-1 human pancreatic cancer cells under nutrient-deprived conditions—a situation akin to the pancreatic cancer tumor microenvironment—over those in nutrient-rich settings, with PC50 values of 0.11 and 47.2 µM, respectively. At a 1 µM concentration, it triggers apoptosis in PANC-1 cells. Furthermore, this compound specifically inhibits the phosphorylation of Akt and mammalian target of rapamycin (mTOR) in PANC-1 cells under nutrient scarcity. In a MiaPaCa-2 pancreatic cancer mouse xenograft model, it significantly reduces tumor volume and weight when administered at 50 and 250 µg/animal dosages five times weekly.

Vitamin K5 (hydrochloride), a naphthoquinone compound, exhibits trichomonacidal activity in vitro and can be utilized for anti-infection research [1].

Angelylalkannin, a naphthoquinone compound isolated from the roots of Alkanna tinctoria, exhibits significant antiproliferative effects on human colon cancer cells HCT-116 and SW-480. The median inhibitory concentration (IC50) of Angelylalkannin is 4.76 mM for HCT-116 cells and 7.03 mM for SW-480 cells. Similar to alkannin, Angelylalkannin induces cell cycle arrest in the G1 phase and cell apoptosis at concentrations ranging from 1-10 mM.

Vitamin K3-d3 is a deuterated compound of Vitamin K3. Vitamin K3 has a CAS number of 58-27-5. Menadione is a synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.