Cinnamaldehyde–cucurbituril complex: investigation of loading efficiency and its role in enhancing cinnamaldehyde <i>in vitro</i> anti-tumor activity

Tbakhi, Bayan; Nsairat, Hamdi; Alshaer, Walhan; Al-Kadash, Abdulfattah; Helal, Wissam; Alrawashdeh, Lubna R.; Day, Anthony I.; Assaf, Khaleel I.; Hassouneh, Rola; Odeh, Fadwa; Bawab, Abeer Al

doi:10.1039/d2ra00044j

Cited by 16 publications

(16 citation statements)

References 44 publications

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“…In other words, the CB7@aCy7 complex is substantially more hydrophilic than free aCy7 . Thus, formulation of azobenzene–cyanine conjugates as their CB7 inclusion complexes is a promising future strategy to increase conjugate water solubility and fine-tune the pharmacokinetics [ 54 ].…”

Section: Resultsmentioning

confidence: 99%

Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates

Kommidi

Smith

2022

Molecules

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Two new azobenzene heptamethine cyanine conjugates exist as dispersed monomeric molecules in methanol solution and exhibit near-infrared (NIR) cyanine absorption and fluorescence. Both conjugates form non-emissive cyanine H-aggregates in water, but the addition of cucurbit[7]uril (CB7) induces dye deaggregation and a large increase in cyanine NIR fluorescence emission intensity. CB7 encapsulates the protonated azonium tautomer of the 4-(N,N-dimethylamino)azobenzene component of each azobenzene–cyanine conjugate and produces a distinctive new absorption band at 534 nm. The complex is quite hydrophilic, which suggests that CB7 can be used as a supramolecular additive to solubilize this new family of NIR azobenzene–cyanine conjugates for future biomedical applications. Since many azobenzene compounds are themselves potential drug candidates or theranostic agents, it should be possible to formulate many of them as CB7 inclusion complexes with improved solubility, stability, and pharmaceutical profile.

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Section: Resultsmentioning

confidence: 99%

Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates

Kommidi

Smith

2022

Molecules

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“…Cucurbit[ n ]urils ( n = 5–8, 10, 13–15) represent a group of supramolecular macrocyclic systems having a pumpkin-shaped structure composed of n glycoluril units bridged by methylene (Me[ n ]) groups, forming a lipophilic cavity that is further attached to a pair of hydrophilic carbonyl groups establishing the two opening entrances of the main structure (Figure ). , …”

Section: Cucurbit[n]urils (Cbs) Host Molecules In Drug Deliverymentioning

confidence: 99%

“…Cucurbit[n]urils (n = 5−8, 10, 13−15) represent a group of supramolecular macrocyclic systems having a pumpkin-shaped structure composed of n glycoluril units bridged by methylene (Me[n]) groups, forming a lipophilic cavity that is further attached to a pair of hydrophilic carbonyl groups establishing the two opening entrances of the main structure (Figure 1). 21,26 CBs have traditionally been synthesized by the condensation of glycoluril and formaldehyde in an acidic medium (Figure 1a). 25 Recently, different modifications of the reaction parameters of the synthesis method, such as manipulating the reaction temperature, duration, and the acid concentration or type, have been introduced to eventually obtain other CBs homologues (CB[n]: n = 5−8, 10) (Figure 1a).…”

Section: Cucurbit[n]urils (Cbs) Host Molecules In Drug Deliverymentioning

confidence: 99%

Stimuli-Responsive Cucurbit[n]uril-Based Supramolecular Nanocarriers for Delivery of Chemotherapeutics

Alabrahim

Fahmy²,

Azzazy

2023

ACS Appl. Nano Mater.

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Chemotherapeutics commonly exhibit low bioavailability and systemic adverse effects. Supramolecular nanovesicles, such as pillar[n]arenes, calix[n]arenes, cucurbit[n]urils (CBs), and cyclodextrins, have been introduced as promising nanocarriers due to their remarkable encapsulation capacity and ability to host hydro-philic/-phobic guest molecules. Additionally, such nanovesicles can be decorated with various stimuli-responsive entities to enable drug targeting and controlled drug release. Self-assembly of amphiphilic cavitands and host−guest complexation represent the two common approaches for preparation of supramolecular nanovesicles with customizable surfaces capable of accommodating different biologically active guest molecules. CBs have been used as smart and multifunctional host macromolecules in cancer therapy. CBs are fabricated via a condensation reaction between formaldehyde and glycoluril units generating barrel-shaped supramolecules with partially enclosed cavities. The unique structure of CBs surrounding an internal hydrophobic cavity allows them to accommodate cationic and neutral guest molecules via ion-dipole and hydrophobic interactions, respectively. Additionally, CBs are stable, safe, and biocompatible, and their surfaces can be decorated with various functional targeting moieties. These advantages have promoted CBs as promising candidates for stimuli-responsive targeted delivery of chemotherapeutics. This review presents the most recent advances in the design of stimuli-responsive nanosystems based on CBs for effective cancer treatment.

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“…Cinnamaldehyde, denoted CA, has already been reported to be one of the most active compounds in cinnamon essential oils, with various biological activities. The reported biological activities of cinnamaldehyde mainly include insecticidal [ 7 ], antibacterial [ 8 , 9 , 10 , 11 ], antifungal [ 12 ], antioxidant [ 13 ], anti-hyperglycemic [ 14 ], anticancer [ 15 , 16 ], and other bioactivities [ 17 ]. Therefore, cinnamaldehyde has attracted widespread and great interest in various fields, especially in the fields of food [ 18 ] and biomedicine [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Cinnamaldehyde-Contained Polymers and Their Biomedical Applications

Zhang

Liu

et al. 2023

Polymers

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Cinnamaldehyde, a natural product that can be extracted from a variety of plants of the genus Cinnamomum, exhibits excellent biological activities including antibacterial, antifungal, anti-inflammatory, and anticancer properties. To overcome the disadvantages (e.g., poor water solubility and sensitivity to light) or enhance the advantages (e.g., high reactivity and promoting cellular reactive oxygen species production) of cinnamaldehyde, cinnamaldehyde can be loaded into or conjugated with polymers for sustained or controlled release, thereby prolonging the effective action time of its biological activities. Moreover, when cinnamaldehyde is conjugated with a polymer, it can also introduce environmental responsiveness to the polymer through the form of stimuli-sensitive linkages between its aldehyde group and various functional groups of polymers. The environmental responsiveness provides the great potential of cinnamaldehyde-conjugated polymers for applications in the biomedical field. In this review, the strategies for preparing cinnamaldehyde-contained polymers are summarized and their biomedical applications are also reviewed.

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Cinnamaldehyde–cucurbituril complex: investigation of loading efficiency and its role in enhancing cinnamaldehyde in vitro anti-tumor activity

Abstract: This study aimed to clarify the physico-chemical properties of cucurbit[7]uril (CB[7]) and cinnamaldehyde (Cinn) inclusion complexes (CB[7]–Cinn) and their resulting antitumor activity.

Cited by 16 publications

References 44 publications

Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates

Cucurbit[7]uril Complexation of Near-Infrared Fluorescent Azobenzene-Cyanine Conjugates

Stimuli-Responsive Cucurbit[n]uril-Based Supramolecular Nanocarriers for Delivery of Chemotherapeutics

Cinnamaldehyde-Contained Polymers and Their Biomedical Applications

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