Inclusion Complexation of the Sunscreen 2-Hydroxy-4-Methoxy Benzophenone (Oxybenzone) with Hydroxypropyl-?-Cyclodextrin: Effect on Membrane Diffusion

Sarveiya, Vikram; Templeton, J. F.; Benson, Heather A. E.

doi:10.1007/s10847-004-6098-6

Cited by 23 publications

(5 citation statements)

References 22 publications

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“…[27][28][29]35,64,69] To this point, hydrophilic CDs have been added to sunscreen formulations to reduce absorption of lipophilic sunscreen agents into skin. [23,[69][70][71] Topical drug delivery to the eye Examples of CD-containing ophthalmic formulations and topical drug delivery to the eye are listed in Table 3. The aqueous tear fluid and the mucus layer on the eye surface form an aqueous diffusion barrier for topical drug delivery to the eye.…”

Section: Dermal and Transdermal Drug Deliverymentioning

confidence: 99%

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Loftsson

Brewster

2011

Journal of Pharmacy and Pharmacology

241

126

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Objectives Cyclodextrins are useful solubilizing excipients that have gained currency in the formulator's armamentarium based on their ability to temporarily camouflage undesirable physicochemical properties. In this context cyclodextrins can increase oral bioavailability, stabilize compounds to chemical and enzymatic degradation and can affect permeability through biological membranes under certain circumstances. This latter property is examined herein as a function of the published literature as well as work completed in our laboratories. Key findings Cyclodextrins can increase the uptake of drugs through biological barriers if the limiting barrier component is the unstirred water layer (UWL) that exists between the membrane and bulk water. This means that cyclodextrins are most useful when they interact with lipophiles in systems where such an UWL is present and contributes significantly to the barrier properties of the membrane. Furthermore, these principles are used to direct the optimal formulation of drugs in cyclodextrins. A second related critical success factor in the formulation of cyclodextrin-based drug product is an understanding of the kinetics and thermodynamics of complexation and the need to optimize the cyclodextrin amount and drug-to-cyclodextrin ratios. Drug formulations, especially those targeting compartments associated with limited dissolution (i.e. the eye, subcutaneous space, etc.), should be carefully designed such that the thermodynamic activity of the drug in the formulation is optimal meaning that there is sufficient cyclodextrin to solubilize the drug but not more than that. Increasing the cyclodextrin concentration decreases the formulation 'push' and may reduce the bioavailability of the system. Conclusions A mechanism-based understanding of cyclodextrin complexation is essential for the appropriate formulation of contemporary drug candidates.

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Section: Dermal and Transdermal Drug Deliverymentioning

confidence: 99%

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Loftsson

Brewster

2011

Journal of Pharmacy and Pharmacology

241

126

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“…The effect of employing CD-UV filters inclusion complexes on the overall SPF value of the formulation was investigated. While some studies reported negligible to minor increases in the formulation SPF when CD-UV filters inclusion complexes were used [ 84 , 85 ], other reported more significant effects. For instance, Srinivasan et al measured the SPF values of two commercial sunscreens with and without β-CD complexes of different dinitro compounds (dinitrophenol, dinitroaniline, and dinitrobenzoic acid).…”

Section: Cyclodextrins (Cds)mentioning

confidence: 99%

Sunscreens Containing Cyclodextrin Inclusion Complexes for Enhanced Efficiency: A Strategy for Skin Cancer Prevention

et al. 2021

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Unprotected exposure of skin to solar ultraviolet radiation (UVR) may damage the DNA of skin cells and can lead to skin cancer. Sunscreens are topical formulations used to protect skin against UVR. The active ingredients of sunscreens are UV filters that absorb, scatter, and/or reflect UVR. Preventing the formation of free radicals and repairing DNA damages, natural antioxidants are also added to sunscreens as a second fold of protection against UVR. Antioxidants can help stabilise these formulations during the manufacturing process and upon application on skin. However, UV filters and antioxidants are both susceptible to degradation upon exposure to sunlight and oxygen. Additionally, due to their poor water solubility, natural antioxidants are challenging to formulate and exhibit limited penetration and bioavailability in the site of action (i.e., deeper skin layers). Cyclodextrins (CDs) are cyclic oligosaccharides that are capable of forming inclusion complexes with poorly soluble drugs, such as antioxidants. In this review, we discuss the use of CDs inclusion complexes to enhance the aqueous solubility of antioxidants and chemical UV filters and provide a protective shield against degradative factors. The role of CDs in providing a controlled drug release profile from sunscreens is also discussed. Finally, incorporating CDs inclusion complexes into sunscreens has the potential to increase their efficiency and hence improve their skin cancer prevention.

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“…Some investigations that focussed on measuring the total amount of BZ3 excreted in human urine after repeated topical whole-body applications of a sunscreen have established that between 0.4% and 3.7% [11][12][13] of the total amount of BZ3 applied was excreted in this way [14]. Other studies have determined maximum median urine concentrations ranging from 7 to 260 ng mL −1 [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

“…However, there are very few reports focused on this topic, which have been recently reviewed [10]. Thus, while BZ3 has been previously determined in human urine by gas chromatography-mass spectrometry (GC-MS) [15] and liquid chromatography-UV spectrometry (LC-UV) [11][12][13]17], no papers about the determination of BZ4 in human urine have been previously published.…”

Section: Introductionmentioning

confidence: 99%

Development of a fully automated sequential injection solid-phase extraction procedure coupled to liquid chromatography to determine free 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid in human urine

León

Chisvert

Balaguer

et al. 2010

Analytica Chimica Acta

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Inclusion Complexation of the Sunscreen 2-Hydroxy-4-Methoxy Benzophenone (Oxybenzone) with Hydroxypropyl-?-Cyclodextrin: Effect on Membrane Diffusion

Cited by 23 publications

References 22 publications

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes

Sunscreens Containing Cyclodextrin Inclusion Complexes for Enhanced Efficiency: A Strategy for Skin Cancer Prevention

Development of a fully automated sequential injection solid-phase extraction procedure coupled to liquid chromatography to determine free 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid in human urine

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