Triclosan
Triclosan is a synthetic, lipid soluble broad-spectrum antibacterial and antifungal agent which is widely used in personal care products, household items, medical devices, and fabrics and plastics. It, distributed ubiquitously across the ecosystem, possesses intrinsic oestrogenic and androgenic activity which could provide some explanation for the endocrine disrupting properties described in aquatic species.
In vitro: Triclosan blocked and displaced [3H] oestradiol binding from oestrogen receptors (ER) of MCF7 human breast cancer cells and from recombinant human ERα /ERβ at low concentrations. Triclosan fully dampened the elicitation of the oestrogen-responsive ERE-CAT reporter gene in MCF7 cells and the activation of growth of MCF7 human breast cancer cells by 10-10 M 17β-oestradiol. Additionally, Triclosan, on its own, increased the proliferation of oestrogen-dependent MCF7 human breast cancer cells [1].
In vivo: BALB/c mice were administrated subcutaneously with triclosan daily at 0.8 to 38 mg/kg for 6 weeks. 75% parasitemia was blocked by single subcutaneous injection of triclosan at a dose of 3.0 mg/kg within 24 hours. However, triclosan fully cleared the parasite from circulation with one injection at a dose of 38 mg/kg. No side effects of triclosan were monitored via checking the activities of the enzymes serum glutamate oxaloacetate transaminase and serum glutamate pyruvate transaminase [2].
References:
[1].? Gee, R., Charles, A., Taylor, N., & Darbre, P. Oestrogenic and androgenic activity of triclosan in breast cancer cells. Journal of Applied Toxicology. 2007; 28(1): 78-91.
[2].? Hillyer, C. Triclosan offers protection against blood stages of malaria by inhibiting enoyl-ACP reductase of Plasmodium falciparumM. Surolia, A. Surolia. Nat Med 7:167–173, 2001. Transfusion Medicine Reviews. 2002; 16(2): 180-181.
| Storage | Store at RT |
| M.Wt | 289.5 |
| Cas No. | 3380-34-5 |
| Formula | C12H7Cl3O2 |
| Solubility | insoluble in H2O; ≥10.95 mg/mL in DMSO; ≥47.7 mg/mL in EtOH |
| Chemical Name | 5-chloro-2-(2,4-dichlorophenoxy)-phenol |
| SDF | Download SDF |
| Canonical SMILES | ClC1=C(OC2=CC=C(Cl)C=C2O)C=CC(Cl)=C1 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
Human breast cancer cells |
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Preparation method |
The solubility of this compound in DMSO is ≥ 10.95mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
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Reacting condition |
0～10-4M |
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Applications |
Triclosan blocked and displaced [3H] oestradiol binding from oestrogen receptor (ER) from MCF7 human breast cancer cells and low concentrations of recombinant human ERα / ERβ. Triclosan completely inhibited the induction of oestrogen-responsive ERE-CAT reporter gene in MCF7 cells and 10-10 M17β-estradiol activated MCF7 human breast cancer cell growth. |
| Animal experiment [1]: | |
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Animal models |
BALB / c mice |
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Dosage form |
0.8～38 mg/kg (s.c.) , once a day for six weeks |
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Application |
A single subcutaneous injection of triclosan (a dose of 3.0 mg/kg) with 24 hours can block 75% of parasitic diseases. However, a single injection of triclosan at a dose of 38 mg/kg completely cleared the circulating parasites. By examining the activities of serum glutamate oxaloacetate aminotransferase and serum glutamate pyruvate transaminase, no side effects of triclosan were detected. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Gee RH, Charles A, Taylor N, Darbre PD. Oestrogenic and androgenic activity of triclosan in breast cancer cells. J Appl Toxicol. 2008 Jan;28(1):78-91. doi: 10.1002/jat.1316. PMID: 17992702. [2]. Surolia N, Surolia A. Triclosan offers protection against blood stages of malaria by inhibiting enoyl-ACP reductase of Plasmodium falciparum. Nat Med. 2001 Feb;7(2):167-73. doi: 10.1038/84612. Erratum in: Nat Med 2001 May;7(5)636. PMID: 11175846. |
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Quality Control & MSDS
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Chemical structure
