Targeted Nanogel Conjugate for Improved Stability and Cellular Permeability of Curcumin: Synthesis, Pharmacokinetics, and Tumor Growth Inhibition

Wei, Xin; Senanayake, Thulani H.; Bohling, Anna; Vinogradov, Serguei V.

doi:10.1021/mp500290f

Cited by 74 publications

(39 citation statements)

References 33 publications

(92 reference statements)

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“…It has been reported that the stability of curcumin increases when bound to plasma proteins or loaded in nanoformulations (39)(40)(41). We therefore studied the degradation of curcumin in two different formulations, namely loaded in mPEG-HPMA-Bz micelles and in Triton X-100 micelles.…”

Section: Degradation Of Curcumin (As Curcuminoid Mixture) Loaded In Mmentioning

confidence: 99%

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

Naksuriya

Steenbergen

Toraño

et al. 2016

AAPS J

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Abstract. Curcumin, a phenolic compound, possesses many pharmacological activities and is under clinical evaluation to treat different diseases. However, conflicting data about its stability have been reported. In this study, the kinetic degradation of curcumin from a natural curcuminoid mixture under various conditions (pH, temperature, and dielectric constant of the medium) was investigated. Moreover, the degradation of pure curcumin at some selected conditions was also determined. To fully solubilize curcumin and to prevent precipitation of curcumin that occurs when low concentrations of co-solvent are present, a 50:50 (v/v) aqueous buffer/methanol mixture was used as standard medium to study its degradation kinetics. The results showed that degradation of curcumin both as pure compound and present in the curcuminoid mixture followed first order kinetic reaction. It was further shown that an increasing pH, temperature, and dielectric constant of the medium resulted in an increase in the degradation rate. Curcumin showed rapid degradation due to autoxidation in aqueous buffer pH=8.0 with a rate constant of 280×10 -3 h -1, corresponding with a half-life (t 1/2 ) of 2.5 h. Dioxygenated bicyclopentadione was identified as the final degradation product. Importantly, curcumin loaded as curcuminoid mixture in ω-methoxy poly (ethylene glycol)-b-(N-(2-benzoyloxypropyl) methacrylamide) (mPEG-HPMA-Bz) polymeric micelles and in Triton X-100 micelles was about 300-500 times more stable than in aqueous buffer. Therefore, loading of curcumin into polymeric micelles is a promising approach to stabilize this compound and develop formulations suitable for further pharmaceutical and clinical studies.

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Section: Degradation Of Curcumin (As Curcuminoid Mixture) Loaded In Mmentioning

confidence: 99%

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

Naksuriya

Steenbergen

Toraño

et al. 2016

AAPS J

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“…Shinde and Devarajan 27 reported that microemulsions composed of docosahexaenoic acid could effectively deliver CUR to the brain and inhibit the growth of human glioblastoma U-87MG cell line in vitro. Wei et al 28 demonstrated that cholesteryl-hyaluronic acid nanogel of CUR exhibited excellent solubility and sustained drug release under physiological conditions and effectively inhibited human pancreatic adenocarcinoma MiaPaCa-2 cells. Jyoti et al 29 investigated chitosan (CS) microspheres of CUR and showed that the microspheres improved solubility and therapeutic index of CUR in HT-29 cells.…”

Section: Introductionmentioning

confidence: 99%

Liposomal curcumin and its application in cancer

Feng¹,

Wei²,

Lee³

et al. 2017

IJN

301

208

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Curcumin (CUR) is a yellow polyphenolic compound derived from the plant turmeric. It is widely used to treat many types of diseases, including cancers such as those of lung, cervices, prostate, breast, bone and liver. However, its effectiveness has been limited due to poor aqueous solubility, low bioavailability and rapid metabolism and systemic elimination. To solve these problems, researchers have tried to explore novel drug delivery systems such as liposomes, solid dispersion, microemulsion, micelles, nanogels and dendrimers. Among these, liposomes have been the most extensively studied. Liposomal CUR formulation has greater growth inhibitory and pro-apoptotic effects on cancer cells. This review mainly focuses on the preparation of liposomes containing CUR and its use in cancer therapy.

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“…It is well known that curcumin is a lipophilic molecule and has been extensively used in food, medicines, and cosmetics due to its various bioactivities [17][18][19][20][21]. However, its delivery is highly limited by its insolubility and instability in biological fluids [22][23][24][25]. So far, it is yet to fulfill its clinical promise in part due to pH-mediated instability [26].…”

Section: Introductionmentioning

confidence: 99%

Effects of Micro-environmental pH of Liposome on Chemical Stability of Loaded Drug

et al. 2017

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Liposome is a promising carrier system for delivering bioactive molecules. However, the successful delivery of pH-sensitive molecules is still limited by the intrinsic instability of payloads in physiological environment. Herein, we developed a special liposome system that possesses an acidic micro-environment in the internal aqueous chamber to improve the chemical stability of pH-sensitive payloads. Curcumin-loaded liposomes (Cur-LPs) with varied internal pH values (pH 2.5, 5.0, or 7.4) were prepared. These Cur-LPs have similar particle size of 300 nm, comparable physical stabilities and analogous in vitro release profiles. Interestingly, the chemical stability of liposomal curcumin in 50% fetal bovine serum and its anticancer efficacy in vitro are both micro-environmental pH-dependent (Cur-LP-2.5 > Cur-LP-5.0 > Cur-LP-7.4). This serum stability still has space to be further enhanced to improve the applicability of Cur-LP. In conclusion, creating an acidic micro-environment in the internal chamber of liposome is feasible and efficient to improve the chemical stability of pH-sensitive payloads.

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Targeted Nanogel Conjugate for Improved Stability and Cellular Permeability of Curcumin: Synthesis, Pharmacokinetics, and Tumor Growth Inhibition

Cited by 74 publications

References 33 publications

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

A Kinetic Degradation Study of Curcumin in Its Free Form and Loaded in Polymeric Micelles

Liposomal curcumin and its application in cancer

Effects of Micro-environmental pH of Liposome on Chemical Stability of Loaded Drug

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