CAS 3380-34-5 Triclosan - Analytical Products / Alfa Chemistry

CAT	APS3380345
CAS	3380-34-5
Structure
Synonyms	Triclosan, Sapoderm, Ster-Zac, 5-Chloro-2-(2,4-dichlorophenoxy)phenol, Irgasan DP 300, 2,4,4'-trichloro-2'-hydroxydiphenyl ether, Aquasept, CH-3635, Gamophen
IUPAC Name	5-chloro-2-(2,4-dichlorophenoxy)phenol
Molecular Weight	289.54
Molecular Formula	C12H7Cl3O2
Canonical SMILES	Oc1cc(Cl)ccc1Oc2ccc(Cl)cc2Cl
InChI	InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H

Accurate Mass	287.9512
Format	Neat

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Case Study

Triclosan Inhibits Testosterone Biosynthesis in Adult Rats

Sang, J., Ji, Z., Li, H., Wang, H., Quan, H., Yu, Y., ... & Lin, H. (2024). Environment International, 108827.

Triclosan is a potent antibacterial compound widely used in everyday products. However, it remains unclear whether triclosan affects the function of Leydig cells in the testes of adult male rats.
In this study, Sprague-Dawley male rats were orally administered 0, 50, 100, or 200 mg/kg/day of triclosan from postnatal days 56 to 63. Triclosan significantly reduced serum testosterone levels at 100-200 mg/kg by downregulating the expression of Leydig cell genes such as Lhcgr, Scarb1, Star, Cyp11a1, Hsd3b1, Cyp17a1, and Hsd17b3, as well as regulating the expression of the transcription factor Nr3c2. Further analysis revealed that triclosan significantly increased autophagy, as evidenced by elevated levels of LC3II and BECN1 and reduced levels of SQSTM1.
mRNA m6A modification analysis indicated that triclosan at 200 mg/kg significantly downregulated the expression of Fto, while both 100 and 200 mg/kg upregulated Ythdf1 expression. MeRIP analysis demonstrated methylation of Becn1 mRNA. At concentrations of ≥5 μM, triclosan significantly inhibited testosterone output from rat R2C Leydig cells by downregulating Fto and upregulating Ythdf1. Silencing Ythdf1 with SiRNA reversed triclosan-mediated mitochondrial autophagy in R2C cells, thereby reversing the reduction in testosterone output.
In conclusion, triclosan reduces testosterone biosynthesis by downregulating Fto and upregulating Ythdf1, leading to m6A methylation of Becn1, which accelerates Becn1 translation and promotes autophagy.

Triclosan Increases the Transformation Frequency of Antibiotic Resistance Genes

Lu, J., Wang, Y., Zhang, S., Bond, P., Yuan, Z., & Guo, J. (2020). Science of the Total Environment, 713, 136621.

The spread of antibiotic resistance is mediated by the horizontal transfer of antibiotic resistance genes (ARGs), exacerbating the global antibiotic crisis. Currently, little is known about whether non-antibiotic antimicrobial (NAAM) chemicals are related to the spread of resistance genes in the environment.
This study evaluated whether triclosan (TCS), a widely present NAAM chemical, can promote the transformation of plasmid-borne antibiotic resistance genes (ARGs). Using the plasmid pUC19, which carries an ampicillin resistance gene, as the extracellular resistance gene and the model microorganism Escherichia coli DH5ɑ as the recipient, it was found that TCS significantly enhanced the transformation of plasmid-borne resistance genes into E. coli DH5ɑ at environmentally relevant concentrations (0.2 μg/L to 20 μg/L), with an increase of up to 1.4 times.
Combining phenotypic experiments, whole-genome RNA sequencing, and proteomics analysis, it was discovered that TCS exposure stimulated reactive oxygen species (ROS) production by 1.3 to 1.5 times, leading to bacterial membrane damage and upregulation of the translation of outer membrane porins. Additionally, TCS enhanced the general secretion system Sec (1.4 times), the twin-arginine translocation system Tat (1.2 times), and the type IV pilus secretion system (2.5 times), which may assist in pilus-mediated DNA search and capture.
In summary, TCS may increase the transformation frequency of ARGs into E. coli DH5ɑ by excessively producing ROS, disrupting the cellular membrane barrier, mediating pilus capture of plasmids, and facilitating plasmid translocation through membrane channels.

Preparation of Triclosan-Loaded Micelles

Su, Yuling, et al. Materials Science and Engineering: C 93 (2018): 921-930.

Triclosan-loaded polyurethane micelles are pH and lipase sensitive, making them suitable for antibacterial applications and biofilm treatment.
Preparation of Triclosan-Loaded Micelles: Triclosan-loaded polyurethane micelles were prepared using a dialysis method. Typically, polyurethane (PEG-c-PU, PEG-g-PU, or PEG-b-PU, 20 mg) and triclosan (TLS, 15 mg) were added to 4 mL of dimethylformamide (DMF) and stirred for 1 hour. The clear solution was then added dropwise to 15 mL of deionized water. Subsequently, the micelle solution was transferred to a dialysis bag (MWCO, 8-14 kDa) and dialyzed in distilled water for 72 hours, resulting in a triclosan-loaded PU micelle concentration of 1.0 mg/mL. The resulting aqueous solution was centrifuged at 10,000 rpm for 5 minutes, and then filtered through a 0.45 μm PTFE syringe filter to remove unbound triclosan.