Effect of hydroxypropyl-β-cyclodextrin on the solubility, photostability and in-vitro permeability of alkannin/shikonin enantiomers

Chen, Chau-Yang; Chen, Fu‐An; Wu, An‐Bang; Hsu, Hsingchu; Kang, Jaw Jou; Cheng, Hui-Wen

doi:10.1016/0378-5173(96)04634-0

Cited by 27 publications

(15 citation statements)

References 19 publications

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“…In order to improve the stability and water solubility of shikonin, several approaches have been tried. Thus, in 1996, Chen et al [6] were able to achieve an approximate 200-fold increase in the solubility, photostability, and in vitro permeability of shikonin through the formation of a 1 : 1 inclusion complex with hydroxypropyl-β-cyclodextrin. In 2004, Assimopoulou and Papageorgiou [5] confirmed these results in a study in which they explored the inclusion of shikonin, alkannin, and their derivatives in β-cyclodextrin and hydroxypropyl-β-cyclodextrin.…”

Section: The Pharmacokinetics and Bioavailability Of Shikoninmentioning

confidence: 99%

Pharmacological Properties of Shikonin – A Review of Literature since 2002

et al. 2013

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!The naphthoquinone shikonin is the main active principle of Zicao, a traditional Chinese herbal medicine made from the dried root of Lithospermum erythrorhizon. Studies carried out over the past 30 years have provided a scientific basis for the use of Zicao which has been long employed in folk medicine to treat a variety of inflammatory and infectious diseases. In particular, shikonin has been shown to possess many diverse properties, including antioxidant, anti-inflammatory, antithrombotic, antimicrobial, and wound healing effects. The fact that shikonin shows so many beneficial properties has increased the interest in this molecule dramatically, especially in the past few years. The aim of this review is to provide an update of the new data published on shikonin, whose wide spectrum of pharmacological effects as well as pharmacokinetic properties and toxicity make it a highly interesting target molecule.

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Section: The Pharmacokinetics and Bioavailability Of Shikoninmentioning

confidence: 99%

Pharmacological Properties of Shikonin – A Review of Literature since 2002

et al. 2013

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“…Acitretin RMbCD [21] Alkannin HPbCD [22] Avobenzone HPbCD [23] Beclometasone dipropionate gCD [24] 4-Biphenylylacetic acid bCD, DMbCD, HPbCD [25,26] Bupranolol HPbCD, MbCD [27] Capsaicin HPbCD [28] Celecoxib DMbCD [29] Curcumin HPbCD, HPgCD [30] Dexamethasone acetate bCD, HPbCD [31] 17b-Estradiol HPbCD [32] Hydrocortisone bCD, CMbCD, HPbCD, MLbCD, RMbCD [32][33][34][35][36][37][38][39] Ibuprofen HPbCD [40] Indometacin bCD, DEbCD, DMbCD [41,42] Ketoprofen HPbCD [43] Liarozole HPbCD [44] Lidocaine DMbCD, HPbCD, SBEbCD [45] Loteprednol etabonate DMbCD [46] Melatonin HPbCD [47] Metopimazine MbCD [48] Methyl paraben HPbCD [49] Miconazole aCD, HPbCD [50] Naproxen bCD [51] Piribedil RMbCD [52] Piroxicam HPbCD [53,54] Prednisolone bCD, gCD [55] Prostaglandin E1 aCD, bCD, CMEbCD, [56][57][58][59] Shikonin HPbCD [22] Sulfanilic acid bCD, DMbCD [41] Testosterone HPbCD [32] Tolnaftate bCD, bCD-polymer [60] Tretinoin bCD, H...…”

Section: Drugmentioning

confidence: 99%

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

Loftsson

Brewster

2011

Journal of Pharmacy and Pharmacology

233

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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“…Encapsulation of isohexenylnaphthazarins 241 ORIGINAL RESEARCH β-Hydroxypropyl cyclodextrin (β-HPCD) has been used for the inclusion of shikonin isolated from Macrotomia euchroma roots in a cream and gel formulation (Chen et al, 1996b). The effect of β-HPCD on solubility, photostability and in vitro permeability of A/S contained in creams and gels was examined.…”

Section: Introductionmentioning

confidence: 99%

Encapsulation of isohexenylnaphthazarins in cyclodextrins

Assimopoulou

Papageorgiou

2004

Biomedical Chromatography

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Naturally occurring isohexenylnaphthazarins (IHN), such as Alkannin, Shikonin (A/S) and their derivatives, are potent pharmaceutical substances with a wide spectrum of biological activity. In the present study, inclusion complexes of alkannin and shikonin commercial samples and IHN derivatives in the form of an oily extract of Alkanna tinctoria roots were formed with beta-cyclodextrin (CD) and beta-HPCD. These complexes were investigated to evaluate the effect of complexation on their aqueous solubility, decoloration, and also the percentage of polymeric A/S and IHN derivatives enclosed in the CDs cavity, since these decrease the active monomeric IHN. Both beta-CD and beta-HPCD increased the aqueous solubility of A/S and IHN derivatives and thus inclusion complexes can be used as drug delivery systems for A/S in both internal (capsules, tablets) and external hydrophilic pharmaceutical and cosmetic preparations (creams, gels, sprays) with enhanced bioavailability. The inclusion complexes formed had a pale purple colour, contributing to the partial decoloration of the A/S and thus of the fi nal pharmaceutical preparations. Finally, CDs selectively included more monomeric and less polymeric IHN, compared with the initial each time sample that is encapsulated; thus inclusion complexes may present enhanced biological activity.

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Effect of hydroxypropyl-β-cyclodextrin on the solubility, photostability and in-vitro permeability of alkannin/shikonin enantiomers

Cited by 27 publications

References 19 publications

Pharmacological Properties of Shikonin – A Review of Literature since 2002

Pharmacological Properties of Shikonin – A Review of Literature since 2002

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

Encapsulation of isohexenylnaphthazarins in cyclodextrins

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