Carvacrol Prodrugs with Antimicrobial Activity Loaded on Clay Nanocomposites

Abstract

Background: Carvacrol, an essential oil with antimicrobial activity against a wide range of pathogens, and its water soluble carvacrol prodrugs (WSCP1-3) were intercalated into montmorillonite (VHS) interlayers to improve their stability in physiological media and promote their absorption in the intestine. Methods: Intercalation of prodrugs by cation exchange with montmorillonite interlayer counterions was verified by X-ray powder diffraction and confirmed by Fourier transform infrared spectroscopy and thermal analysis. Results: In vitro release studies demonstrated that montmorillonite successfully controlled the release of the adsorbed prodrugs and promoted their bioactivation only in the intestinal tract where carvacrol could develop its maximum antimicrobial activity. The amount of WSCP1, WSCP2, and WSCP3 released from VHS were 38%, 54%, and 45% at acid pH in 120 min, and 65%, 78%, and 44% at pH 6.8 in 240 min, respectively. Conclusions: The resultant hybrids successfully controlled conversion of the prodrugs to carvacrol, avoiding premature degradation of the drug.

Phytotoxic and Antimicrobial Activities of Teucrium polium and Thymus decussatus Essential Oils Extracted Using Hydrodistillation and Microwave-Assisted Techniques

“…The strong antimicrobial activity of T. decussatus could be attributed to the major compounds of the EO, such as carvacrol and p -cymene. Several studies reported the antimicrobial activity of carvacrol and p -cymene [ 59 , 62 , 63 , 64 ].…”

In Vitro Wound-Healing Properties of Water-Soluble Terpenoids Loaded on Halloysite Clay

“…After centrifugation at 10,000 rpm, the solid hybrids were recovered and dried for subsequent investigations. To quantify the amounts of T1-3 retained by the HAL powder, supernatants were examined as previously reported by High-Performance Liquid Chromatography (HPLC) [ 15 , 17 ].…”

“…They showed antimicrobial activities and increased water solubility compared to CAR ( Table 1 ) [ 14 ]. In our previous works, hybrids of T1-3 and layered montmorillonite or fibrous palygorskite and sepiolite were formulated to obtain their sustained release in the target site [ 15 , 16 ].…”

Synthesis and Biological Evaluation of Novel Cinnamic Acid-Based Antimicrobials

“…As reported by the World Health Organization (WHO), antibiotics are becoming progressively ineffective as drug resistance extends worldwide leading to infections that are difficult or impossible to manage [1]. Several reasons are responsible for AMR such as an inappropriate use of antibiotics, microbial behavior, gene transfer, or antioxidant, and wound healing properties [22]. It is a good antibacterial agent against both Gram-positive and -negative bacteria exerting its antimicrobial activity by disrupting bacterial membrane, bacterial lysis, and leading to leakage of intracellular contents.…”

“…Pharmaceuticals 2022, 14, x FOR PEER REVIEW 3 of 18 pathogens (Figure 1). Notably, carvacrol was chosen as the phytochemical component to conjugate to the series of cinnamic acids helpful by virtue of its wide natural antimicrobial, antioxidant, and wound healing properties [22]. It is a good antibacterial agent against both Gram-positive and -negative bacteria exerting its antimicrobial activity by disrupting bacterial membrane, bacterial lysis, and leading to leakage of intracellular contents.…”