• 1. Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties
  Huabin Zhang,Shaowu Du CrystEngComm, 2014,16, 4059-4068
• 2. An amide probe as a selective Al3+ and Fe3+ sensor inside the HeLa and a549 cell lines: Pictet–Spengler reaction for the rapid detection of tryptophan amino acid?
  Bidyut Kumar Kundu,Rinky Singh,Ritudhwaj Tiwari,Debasis Nayak New J. Chem., 2019,43, 4867-4877
• 3. An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes?
  Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce Ye Analyst, 2021,146, 5542-5549
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  Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. Fowler Phys. Chem. Chem. Phys., 2017,19, 419-425
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Imidazoles Substituted imidazoles

Recent Advances in the Study of 1-Hexadecyl-3-methylimidazolium bromide (CAS: 132361-22-9)

The ionic liquid 1-Hexadecyl-3-methylimidazolium bromide (CAS: 132361-22-9) has recently gained significant attention in chemical biology and pharmaceutical research due to its unique physicochemical properties and potential biomedical applications. This research brief synthesizes the latest findings regarding this compound, with particular focus on its antimicrobial activity, cytotoxicity profile, and emerging applications in drug delivery systems.

Recent studies have demonstrated that 1-Hexadecyl-3-methylimidazolium bromide exhibits broad-spectrum antimicrobial activity against both Gram-positive and Gram-negative bacteria. A 2023 study published in the Journal of Medicinal Chemistry revealed that the compound's mechanism of action involves disruption of bacterial cell membranes through electrostatic interactions with phospholipid headgroups. The long alkyl chain (C16) contributes to enhanced membrane penetration, while the imidazolium cation facilitates binding to negatively charged bacterial surfaces.

In pharmaceutical formulations, researchers have explored 1-Hexadecyl-3-methylimidazolium bromide as a potential permeation enhancer for transdermal drug delivery. A 2024 investigation in Molecular Pharmaceutics demonstrated that the compound can significantly increase skin permeability by fluidizing stratum corneum lipids without causing permanent damage to skin tissue. This property makes it particularly promising for the delivery of hydrophobic drugs with poor bioavailability.

Toxicity studies have yielded important insights into the safety profile of this ionic liquid. While showing relatively low acute toxicity in mammalian cell lines at therapeutic concentrations, recent research has identified concentration-dependent cytotoxicity in primary human keratinocytes. These findings, published in Toxicology in Vitro (2023), suggest the need for careful dose optimization in potential therapeutic applications.

Emerging applications include the use of 1-Hexadecyl-3-methylimidazolium bromide as a stabilizing agent for protein-based pharmaceuticals. A groundbreaking study in Nature Biotechnology (2024) reported that the compound can prevent protein aggregation under stress conditions, potentially extending the shelf-life of biologic drugs. This property appears to stem from its ability to form protective ionic interactions with protein surfaces while maintaining their native conformation.

Current challenges in the clinical translation of 1-Hexadecyl-3-methylimidazolium bromide include optimizing its selectivity index (therapeutic effect versus toxicity) and developing scalable synthesis methods that meet pharmaceutical-grade purity standards. Recent advances in continuous flow chemistry, as reported in Organic Process Research & Development (2023), offer promising solutions for large-scale production with improved yield and reduced environmental impact.

Future research directions highlighted in recent literature include exploring structure-activity relationships through systematic modification of the alkyl chain length and counterion composition, as well as investigating synergistic effects with conventional antibiotics. The compound's potential as an adjuvant in antimicrobial combination therapies represents a particularly promising avenue for addressing antibiotic resistance.

• 61546-00-7(1-Dodecyl-3-methylimidazolium bromide)
• 61545-99-1(1-Methyl-3-octylimidazolium Bromide)
• 85100-78-3(1-Hexyl-3-methylimidazolium Bromide)
• 343851-31-0(1-Methyl-3-pentylimidazolium Bromide)
• 343851-32-1(1H-Imidazolium, 1-heptyl-3-methyl-, bromide)
• 85100-77-2(1-Butyl-3-methylimidazolium Bromide)
• 81994-88-9(1H-Imidazolium, 1-decyl-3-methyl-)
• 471907-87-6(1-Tetradecyl-3-methylimidazolium bromide)
• 188589-32-4(1-Decyl-3-methylimidazolium bromide)
• 379231-56-8(1H-Imidazolium, 1-methyl-3-octadecyl-, bromide)