Terameprocol

CAS No.: 24150-24-1

Terameprocol (EM-1421) is a synthetic tetra-methylated derivative of nordihydroguaiaretic acid (NDGA) and transcriptiona

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Description	Terameprocol (EM-1421) is a synthetic tetra-methylated derivative of nordihydroguaiaretic acid (NDGA) and transcriptional inhibitor with potential antiviral, antiangiogenic, and antineoplastic activities. Terameprocol showed the strongest anti-HIV activity.
In vitro	在Vero细胞中，Terameprocol通过抑制Sp1转录因子在HIV长末端重复启动子和α-ICP4启动子上的结合，显示出IC50值分别为11和43.5μM。对于HSV-1的10个通道和HSV-2的4个通道，Terameprocol的IC50值在11.7与4μM之间变化[2]。Terameprocol抑制了依赖Sp1的Cdc2基因表达。在M4N处理的转化C3细胞中，通过抑制依赖Sp1的Cdc2和survivin基因表达，Terameprocol诱导生长停滞和凋亡，从而展现出其抗肿瘤活性[3]。Terameprocol处理抑制了依赖Sp1的survivin基因表达。在暂时性和稳定性质survivin转染的C3细胞中，Terameprocol分别使caspase-3激活降低50%和75%[3]。Terameprocol通过诱导凋亡，以非时间表依赖的方式抑制了多种肿瘤细胞系的生长[4]。Terameprocol抑制了黑色素瘤细胞的DNA合成，并导致细胞周期在G0/G1和G2/M阶段停滞[4]。
In vivo	Terameprocol 显著抑制了裸鼠体内人类肿瘤的生长[5]。Terameprocol 同时抑制了鼠类和人类的黑色素瘤以及人类结肠癌的生长，且没有明显的肝脏或肾脏毒性[4]。在携带人类肿瘤异种移植物（Hep 3B, LNCaP, HT-29, MCF7, 以及 K-562）的裸（nu/nu）鼠中，通过静脉（i.v.）或腹腔内（i.p.）给药的Terameprocol治疗能够降低Cdc2和survivin基因的表达[5]。
Synonyms	tetramethyl Nordihydroguaiaretic Acid, EM-1421
molecular weight	358.47
Molecular formula	C22H30O4
CAS	24150-24-1
Storage	Powder: -20°C for 3 years \| In solvent: -80°C for 1 year
Solubility	DMSO: 27.5 mg/ml (76.71 mM)
References	1. Hwu J R, Tseng W N, Gnabre J, et al. Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation[J]. Journal of medicinal chemistry, 1998, 41(16): 2994-3000. 2. Chen H, Teng L, Li J N, et al. Antiviral activities of methylated nordihydroguaiaretic acids. 2. Targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor tetra-O-methyl-NDGA[J]. Journal of medicinal chemistry, 1998, 41(16): 3001-3007. 3. Chang C C, Heller J D, Kuo J, et al. Tetra-O-methyl nordihydroguaiaretic acid induces growth arrest and cellular apoptosis by inhibiting Cdc2 and survivin expression[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101(36): 13239-13244. 4. Lambert J D, Meyers R O, Timmermann B N, et al. Tetra-O-methylnordihydroguaiaretic acid inhibits melanoma in vivo[J]. Cancer letters, 2001, 171(1): 47-56. 5. Park R, Chang C C, Liang Y C, et al. Systemic treatment with tetra-O-methyl nordihydroguaiaretic acid suppresses the growth of human xenograft tumors[J]. Clinical Cancer Research, 2005, 11(12): 4601-4609.