Nordihydroguaiaretic acid - CAS 500-38-9
Catalog number:
500-38-9
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
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Targets:
Others
Description:
NDGA (Nordihydroguaiaretic acid), also known as masoprocol,  is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. NDGA directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations. This agent may induce apoptosis in susceptible tumor cell populations as a result of disruption of the actin cytoskeleton in association with the activation of stress activated protein kinases (SAPKs). In addition, NDGA inhibits arachidonic acid 5-lipoxygenase (5LOX), resulting in diminished synthesis of inflammatory mediators such as prostaglandins and leukotrines; it may prevent leukocyte infiltration into tissues and the release of reactive oxygen species and, at higher concentrations, may also inhibit cyclooxygenase.
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Synonyms:
INSM-18; INSM18. nordihydroguaiaretic acid; NDGA
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Current Developer:
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1.Targeting arachidonic acid pathway by natural products for cancer prevention and therapy.
Yarla NS1, Bishayee A2, Sethi G3, Reddanna P4, Kalle AM5, Dhananjaya BL6, Dowluru KS7, Chintala R8, Duddukuri GR9. Semin Cancer Biol. 2016 Feb 4. pii: S1044-579X(16)30003-7. doi: 10.1016/j.semcancer.2016.02.001. [Epub ahead of print]
Arachidonic acid (AA) pathway, a metabolic process, plays a key role in carcinogenesis. Hence, AA pathway metabolic enzymes phospholipase A2s (PLA2s), cyclooxygenases (COXs) and lipoxygenases (LOXs) and their metabolic products, such as prostaglandins and leukotrienes, have been considered novel preventive and therapeutic targets in cancer. Bioactive natural products are a good source for development of novel cancer preventive and therapeutic drugs, which have been widely used in clinical practice due to their safety profiles. AA pathway inhibitory natural products have been developed as chemopreventive and therapeutic agents against several cancers. Curcumin, resveratrol, apigenin, anthocyans, berberine, ellagic acid, eugenol, fisetin, ursolic acid, [6]-gingerol, guggulsteone, lycopene and genistein are well known cancer chemopreventive agents which act by targeting multiple pathways, including COX-2. Nordihydroguaiaretic acid and baicalein can be chemopreventive molecules against various cancers by inhibiting LOXs.
2.Targeting arachidonic acid pathway by natural products for cancer prevention and therapy.
Yarla NS1, Bishayee A2, Sethi G3, Reddanna P4, Kalle AM5, Dhananjaya BL6, Dowluru KS7, Chintala R8, Duddukuri GR9. Semin Cancer Biol. 2016 Feb 4. pii: S1044-579X(16)30003-7. doi: 10.1016/j.semcancer.2016.02.001. [Epub ahead of print]
Arachidonic acid (AA) pathway, a metabolic process, plays a key role in carcinogenesis. Hence, AA pathway metabolic enzymes phospholipase A2s (PLA2s), cyclooxygenases (COXs) and lipoxygenases (LOXs) and their metabolic products, such as prostaglandins and leukotrienes, have been considered novel preventive and therapeutic targets in cancer. Bioactive natural products are a good source for development of novel cancer preventive and therapeutic drugs, which have been widely used in clinical practice due to their safety profiles. AA pathway inhibitory natural products have been developed as chemopreventive and therapeutic agents against several cancers. Curcumin, resveratrol, apigenin, anthocyans, berberine, ellagic acid, eugenol, fisetin, ursolic acid, [6]-gingerol, guggulsteone, lycopene and genistein are well known cancer chemopreventive agents which act by targeting multiple pathways, including COX-2. Nordihydroguaiaretic acid and baicalein can be chemopreventive molecules against various cancers by inhibiting LOXs.
3.Jasmonic acid is a crucial signal transducer in heat shock induced sesquiterpene formation in Aquilaria sinensis.
Xu YH1, Liao YC1, Zhang Z1,2, Liu J1, Sun PW1, Gao ZH1, Sui C1, Wei JH1,2. Sci Rep. 2016 Feb 23;6:21843. doi: 10.1038/srep21843.
Agarwood, a highly valuable resinous and fragrant heartwood of Aquilaria plants, is widely used in traditional medicines, incense and perfume. Only when Aquilaria trees are wounded by external stimuli do they form agarwood sesquiterpene defensive compounds. Therefore, understanding the signaling pathway of wound-induced agarwood formation is important. Jasmonic acid (JA) is a well-characterized molecule that mediates a plant's defense response and secondary metabolism. However, little is known about the function of endogenous JA in agarwood sesquiterpene biosynthesis. Here, we report that heat shock can up-regulate the expression of genes in JA signaling pathway, induce JA production and the accumulation of agarwood sesquiterpene in A. sinensis cell suspension cultures. A specific inhibitor of JA, nordihydroguaiaretic acid (NDGA), could block the JA signaling pathway and reduce the accumulation of sesquiterpene compounds. Additionally, compared to SA and H2O2, exogenously supplied methyl jasmonate has the strongest stimulation effect on the production of sesquiterpene compounds.
4.Tetra-O-Methyl Nordihydroguaiaretic Acid Broadly Suppresses Cancer Metabolism and Synergistically Induces Strong Anticancer Activity in Combination with Etoposide, Rapamycin and UCN-01.
Kimura K1, Huang RC1. PLoS One. 2016 Feb 17;11(2):e0148685. doi: 10.1371/journal.pone.0148685. eCollection 2016.
The ability of Tetra-O-methyl nordihydroguaiaretic acid (M4N) to induce rapid cell death in combination with Etoposide, Rapamycin, or UCN-01 was examined in LNCaP cells, both in cell culture and animal experiments. Mice treated with M4N drug combinations with either Etoposide or Rapamycin showed no evidence of tumor and had a 100% survival rate 100 days after tumor implantation. By comparison all other vehicles or single drug treated mice failed to survive longer than 30 days after implantation. This synergistic improvement of anticancer effect was also confirmed in more than 20 cancer cell lines. In LNCaP cells, M4N was found to reduce cellular ATP content, and suppress NDUFS1 expression while inducing hyperpolarization of mitochondrial membrane potential. M4N-treated cells lacked autophagy with reduced expression of BNIP3 and ATG5. To understand the mechanisms of this anticancer activity of M4N, the effect of this drug on three cancer cell lines (LNCaP, AsPC-1, and L428 cells) was further examined via transcriptome and metabolomics analyses.
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CAS 500-38-9 Nordihydroguaiaretic acid

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