401600-86-0

Basic information

• Product Name: Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17b)-
• Synonyms: STX140
• CAS NO: 401600-86-0
• Molecular Formula: C19H28N2O7S2
• Molecular Weight: 460.573
• Mol File: 401600-86-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17b)-(CAS DataBase Reference)
• NIST Chemistry Reference: Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17b)-(401600-86-0)
• EPA Substance Registry System: Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17b)-(401600-86-0)

Safety Data

• Hazardous Substances Data: 401600-86-0(Hazardous Substances Data)

Usage

Description

Estra-1,3,5(10)-triene-3,17-diol, 2-methoxy-, disulfamate, (17b)-, also known as STX140, is an estrogen sulfamate with potent anticancer properties. It effectively inhibits steroid sulfatase, carbonic anhydrase IX and II, and bovine brain tubulin assembly. STX140 demonstrates its efficacy by suppressing the proliferation of various cancer cell lines, including those resistant to conventional treatments. Additionally, it reduces angiogenesis and tumor growth in mouse models, making it a promising candidate for cancer therapy.

Uses

Used in Pharmaceutical Industry:
STX140 is used as an anticancer agent for its ability to inhibit the proliferation of various cancer cell lines, including those resistant to conventional treatments such as adriamycin and cisplatin. Its multi-targeted approach makes it a versatile compound in the fight against cancer.
Used in Cancer Research:
STX140 is utilized in cancer research as a tool to study the mechanisms of action and potential synergistic effects with other chemotherapeutic drugs. Its ability to inhibit steroid sulfatase, carbonic anhydrase IX and II, and tubulin assembly provides valuable insights into the development of novel cancer therapies.
Used in Drug Development:
STX140 is employed in the development of new drugs targeting cancer cells, particularly those with resistance to standard treatments. Its diverse mechanisms of action and proven efficacy in preclinical models make it a valuable starting point for the creation of innovative cancer therapies.
Used in Angiogenesis Inhibition:
STX140 is used to inhibit angiogenesis, a process critical for tumor growth and metastasis. By reducing angiogenesis in mouse models, STX140 demonstrates its potential in limiting the growth and spread of cancerous cells.
Used in Tumor Growth Suppression:
STX140 is applied in the suppression of tumor growth, as evidenced by its effectiveness in reducing tumor growth in MCF-7 and MDA-MB-231 mouse xenograft models. This application highlights its potential as a therapeutic agent for various types of cancer.

Upstream product

• 217792-90-0 (8R,9S,13S,14S,17S)-2-methoxy-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 217792-89-7 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-ol 
• 113680-55-0 (8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 362-07-2 2-Methoxyestradiol 
• 7778-42-9 sulphamoyl chloride 
• 50-28-2 estradiol 

Relevant articles and documents

Synthesis of 2-[11C]methoxy-3,17β-O,O-bis(sulfamoyl) estradiol as a new potential PET agent for imaging of steroid sulfatase (STS) in cancers

Steroid sulfatase (STS) catalyzes the hydrolysis of steroid sulfates to estrones, the main source of estrogens in tumors. Carbonic anhydrase II (CAII) is highly expressed in red blood cells through a coordination of the monoanionic form of the sulfamate moiety to the zinc atom in the enzyme active site, and CAII is highly expressed in several tumors. 2-Methoxy-3,17β-O,O- bis(sulfamoyl)estradiol (5) is a dual-function STS-CAII inhibitor inhibited STS with 39 nM IC50 value selectively over CAII with 379 nM IC 50 value. This compound exhibited potent antiproferative activity with mean graph midpoint value of 87 nM in the NCI 60-cell-line panel, and antiangiogenic in vitro and in vivo activity in an early-stage Lewis lung model as well. The compound has been recently developed as a multitargeted anticancer agent. Both STS and CAII are over-expressed in cancers and have become attractive targets for cancer treatment and molecular imaging of cancer. Here we report the first design and synthesis of 2-[11C]methoxy-3,17β- O,O-bis(sulfamoyl)estradiol ([11C]5) as a new potential imaging agent for biomedical imaging technique positron emission tomography (PET) to image STS in cancers. The authentic standard 5 was synthesized from 17β-estradiol by published procedures in 5 steps with 40% overall chemical yield. The precursor 2-hydroxy-3,17β-O,O-bis(sulfamoyl)estradiol (14a) for radiolabeling was synthesized from 17β-estradiol in 10 steps with 5% overall chemical yield. The target tracer [11C]5 was prepared from the precursor 14a with [11C]CH3OTf through O-[ 11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) purification in 40-50% radiochemical yields based on [ 11C]CO2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB.

2-Substituted estradiol bis-sulfamates, multitargeted antitumor agents: Synthesis, in vitro SAR, protein crystallography, and in vivo activity

The anticancer activities and SARs of estradiol-17-O-sulfamates and estradiol 3,17-O,O-bis-sulfamates (E2bisMATEs) as steroid sulfatase (STS) inhibitors and antiproliferative agents are discussed. Estradiol 3,17-O,O-bis-sulfamates 20 and 21, in contrast t