Complexation of curcumin with 2-aminoethyl diphenyl borate and implications for spatiotemporal fluorescence monitoring

Kang, Yoon Young; Jung, Heesun; Yu, Gyeonghui; Chong, Youhoon; Mok, Hyejung

doi:10.1016/j.ijpharm.2016.10.073

Cited by 17 publications

(17 citation statements)

References 21 publications

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“…The percent of free radical inhibition by each substance was assessed using a DPPH assay, based on a previous study [14]. Ascorbic acid (25 mg) for a positive control was dissolved in distilled water (DW) and diluted with methanol to various concentrations (0, 0.4, 0.8, 1.6, 3.1, 6.2, and 15.6 mg/ml).…”

Section: Dpph Assaymentioning

confidence: 99%

“…To study the bioactivity effect of curcumin complexation with boron-based compounds on curcumin, we selected two boron-based compounds, DPBA and BTZ, as shown in Fig. 1 [14,15]. In our previous study, DPBA was used as a stabilizer for keto-enol tautomer of curcumin, which increased in vivo stability of curcumin [14].…”

Section: Preparation Of Curcumin-/boron-based Compound Complexesmentioning

confidence: 99%

“…1 [14,15]. In our previous study, DPBA was used as a stabilizer for keto-enol tautomer of curcumin, which increased in vivo stability of curcumin [14]. BTZ is a dipeptide boronic acid proteasome inhibitor, which has been used for the treatment of refractory non-small cell lung carcinoma and multiple myeloma [16,17].…”

Section: Preparation Of Curcumin-/boron-based Compound Complexesmentioning

confidence: 99%

“…Moreover, pharmaceutical interest in boron has increased for the development of antifungal, antibacterial, and anticancer drugs [13]. Recently, we reported curcumin complexation with 2-aminoethyl diphenyl borate to improve the in vivo and in vitro stability of curcumin [14]. However, comparative evaluation of free curcumin and formulated curcumin in terms of biological activity and biocompatibility should be performed to better understand and broaden the use of curcumin and boron complexes.…”

Section: Introductionmentioning

confidence: 99%

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Effects of curcumin-/boron-based compound complexation on antioxidant and antiproliferation activity

et al. 2018

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Simple and reproducible formulation strategies are needed to improve the bio-availability of curcumin. In this study, curcumin was successfully complexed with two boron-based compounds: 2-aminoethyl diphenyl borate (DPBA) and bortezomib (BTZ; Velcade Ò). In reversephase high-performance liquid chromatography, DPBA/ curcumin complexes (DPBA/cur) showed delayed elution times compared to those of free curcumin. The UV-visible absorbance peak of DPBA/cur and BTZ and curcumin complexes (BTZ/cur) appeared redshifted. DPBA complexation has a negligible effect on the antioxidant and antiproliferation properties of curcumin for two types of cancer cells: MCF-7 and A549. Thus, curcumin complexation with boron-based compounds could be a method to enhance in vivo stability without loss of bioactivity (i.e., antioxidant and antiproliferation effects).

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Section: Dpph Assaymentioning

confidence: 99%

Section: Preparation Of Curcumin-/boron-based Compound Complexesmentioning

confidence: 99%

Section: Preparation Of Curcumin-/boron-based Compound Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effects of curcumin-/boron-based compound complexation on antioxidant and antiproliferation activity

et al. 2018

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“…However, such investigation is still challenging for certain natural products, such as flavonoids, which are rapidly metabolized in and eliminated from the body, and therefore, only a few methods have been reported. Optical fluorescence imaging [8,9], high-performance liquid chromatography tandem mass spectrometry [10,11], and radioisotope-labeling methods [12][13][14]…”

Section: Introductionmentioning

confidence: 99%

Analysis of the biodistribution of natural products in mice by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

et al. 2018

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Natural products originating from plants have various beneficial pharmacological effects, such as anticancer, antimicrobial, and anti-inflammatory activities, while being nontoxic. Therefore, tremendous efforts have been invested in understanding their bioactivities in the body to facilitate therapeutic target validation. However, such research is still challenging for certain natural products, such as flavonoids, which are rapidly metabolized in and eliminated from the human body. To investigate the bioactivities of such products, particularly in certain tissues, it is necessary to understand their biodistribution in vivo. In this respect, reliable analytical methods with simple and efficient procedures for the in vivo evaluation of natural small molecules are urgently required. In particular, mass spectrometry (MS) can be effectively used to analyze small molecules after tissue extraction, as MS has various advantages including accuracy, simplicity, and high sensitivity. Herein, we report the biodistribution of a natural small molecule by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). After intravenously injecting gomisin H into a mouse as a model natural product, it was extracted from each organ and then analyzed by MALDI-TOF MS. The analysis showed that gomisin H accumulated mainly in the liver and relatively large amounts of the product existed in the kidney and brain compared to those in other tissues.

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Four‐Arm Polymer‐Guided Formation of Curcumin‐Loaded Flower‐Like Porous Microspheres as Injectable Cell Carriers for Diabetic Wound Healing

Yuan

Yang

et al. 2023

Adv Healthcare Materials

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Stem cell injection is an effective approach for treating diabetic wounds; however, shear stress during injections can negatively affect their stemness and cell growth. Cell‐laden porous microspheres could provide shelter for stem cells. We herein designed curcumin‐loaded flower‐like porous microspheres (CFPM) by combining phase inversion emulsification with thermally induced phase separation‐guided four‐arm poly(L‐lactic acid) (B‐PLLA). Notably, the CFPM showed a well‐defined surface topography and inner structure, ensuring a high surface area to enable the incorporation and delivery of a large amount of stem cells and curcumin. The stem cell‐carrying CFPM (BMSC@CFPM) maintained the proliferation, retention and stemness of BMSC, which, in combination with their sustainable curcumin release, facilitated the endogenous production of growth/proangiogenic factors and offered a local anti‐inflammatory function. An in vivo bioluminescence assay demonstrated that BMSC@CFPM could significantly increase the retention and survival of BMSC in wound sites. Accordingly, BMSC@CFPM, with no significant systemic toxicity, could significantly accelerate diabetic wound healing by promoting angiogenesis, collagen reconstruction and M2 macrophage polarization. RNA sequencing further unveiled the mechanisms by which BMSC@CFPM promoted diabetic wound healing by increasing the expression of growth factors and enhancing angiogenesis through the JAK/STAT pathway. Overall, BMSC@CFPM represents a potential therapeutic tool for diabetic wound healing.This article is protected by copyright. All rights reserved

show abstract

Complexation of curcumin with 2-aminoethyl diphenyl borate and implications for spatiotemporal fluorescence monitoring

Cited by 17 publications

References 21 publications

Effects of curcumin-/boron-based compound complexation on antioxidant and antiproliferation activity

Effects of curcumin-/boron-based compound complexation on antioxidant and antiproliferation activity

Analysis of the biodistribution of natural products in mice by using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry

Four‐Arm Polymer‐Guided Formation of Curcumin‐Loaded Flower‐Like Porous Microspheres as Injectable Cell Carriers for Diabetic Wound Healing

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