Bithionol
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| Category | Mycotoxins |
| Catalog number | BBF-03843 |
| CAS | 97-18-7 |
| Molecular Weight | 356.05 |
| Molecular Formula | C12H6Cl4O2S |
| Purity | >98% |
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Description
Bithionol is a clinically approved anti-parasitic drug. It has been shown to inhibit solid tumor growth in several preclinical cancer models. It caused dose-dependent cytotoxicity against all ovarian cancer cell lines.
Specification
| Related CAS | 844-26-8 (sulfoxide) |
| Synonyms | Actamer; Bitin; CP 3438; CP-3438; CP3438; Lorothidol; NSC 47129; NSC-47129; NSC47129 |
| Storage | Store at -20°C |
| IUPAC Name | 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol |
| Canonical SMILES | C1=C(C=C(C(=C1Cl)O)SC2=CC(=CC(=C2O)Cl)Cl)Cl |
| InChI | InChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H |
| InChI Key | JFIOVJDNOJYLKP-UHFFFAOYSA-N |
Properties
| Appearance | White to Off-white Solid |
| Application | Bithionol is one of the biocides commonly used in metalworking fluids. |
| Antibiotic Activity Spectrum | parasites |
| Boiling Point | 444.7°C at 760 mmHg |
| Melting Point | 188°C |
| Density | 1.61 g/cm3 |
| Solubility | Soluble in DMSO (20mg/mL) |
| LogP | log Kow = 5.91 (est) |
Reference Reading
1.Bithionol inhibits ovarian cancer cell growth in vitro - studies on mechanism(s) of action.
Ayyagari VN, Brard L1. BMC Cancer. 2014 Feb 4;14:61. doi: 10.1186/1471-2407-14-61.
BACKGROUND: Drug resistance is a cause of ovarian cancer recurrence and low overall survival rates. There is a need for more effective treatment approaches because the development of new drug is expensive and time consuming. Alternatively, the concept of 'drug repurposing' is promising. We focused on Bithionol (BT), a clinically approved anti-parasitic drug as an anti-ovarian cancer drug. BT has previously been shown to inhibit solid tumor growth in several preclinical cancer models. A better understanding of the anti-tumor effects and mechanism(s) of action of BT in ovarian cancer cells is essential for further exploring its therapeutic potential against ovarian cancer.
2.Assessment of the antitumor potential of Bithionol in vivo using a xenograft model of ovarian cancer.
Ayyagari VN1, Johnston NA, Brard L. Anticancer Drugs. 2016 Apr 7. [Epub ahead of print]
In terms of the concept of 'drug repurposing', we focused on pharmaceutical-grade Bithionol (BT) as a therapeutic agent against ovarian cancer. Our recent in-vitro study provides preclinical data suggesting a potential therapeutic role for BT against recurrent ovarian cancer. BT was shown to cause cell death by caspases-mediated apoptosis. The present preliminary study further explores the antitumor potential of pharmaceutical-grade BT in an in-vivo xenograft model of human ovarian cancer. Nude Foxn1 mice bearing SKOV-3 human ovarian tumor xenografts were treated with titrated doses of BT and the therapeutic efficacy of pharmaceutical BT was determined using bioluminescence imaging. BT-induced changes in cell proliferation and apoptosis were evaluated by Ki-67 immunochemical staining and TUNEL assay. The effect of BT on autotaxin levels in serum, ascitic fluid, and tumor tissue was assessed by colorimetric and western blot techniques. BT treatment did not show antitumor potential or enhanced survival time at any of the doses tested.
3.Bithionol Potently Inhibits Human Soluble Adenylyl Cyclase through Binding to the Allosteric Activator Site.
Kleinboelting S1, Ramos-Espiritu L2, Buck H3, Colis L3, van den Heuvel J4, Glickman JF5, Levin LR3, Buck J3, Steegborn C6. J Biol Chem. 2016 Apr 29;291(18):9776-84. doi: 10.1074/jbc.M115.708255. Epub 2016 Mar 9.
The signaling molecule cAMP regulates functions ranging from bacterial transcription to mammalian memory. In mammals, cAMP is synthesized by nine transmembrane adenylyl cyclases (ACs) and one soluble AC (sAC). Despite similarities in their catalytic domains, these ACs differ in regulation. Transmembrane ACs respond to G proteins, whereas sAC is uniquely activated by bicarbonate. Via bicarbonate regulation, sAC acts as a physiological sensor for pH/bicarbonate/CO2, and it has been implicated as a therapeutic target, e.g. for diabetes, glaucoma, and a male contraceptive. Here we identify the bisphenols bithionol and hexachlorophene as potent, sAC-specific inhibitors. Inhibition appears mostly non-competitive with the substrate ATP, indicating that they act via an allosteric site. To analyze the interaction details, we solved a crystal structure of an sAC·bithionol complex. The structure reveals that the compounds are selective for sAC because they bind to the sAC-specific, allosteric binding site for the physiological activator bicarbonate.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
