Morphology of bile salts micelles and mixed micelles with lipolysis products, from scattering techniques and atomistic simulations

Pabois, Olivia; Ziolek, Robert M.; Lorenz, Christian D.; Prévost, Sylvain; Mahmoudi, Najet; Skoda, Maximilian W. A.; Welbourn, Rebecca J. L.; Valero, Margarita; Harvey, Richard D.; Grundy, Myriam M.-L.; Wilde, Peter J.; Grillo, Isabelle; Dreiss, Cécile A.

doi:10.1016/j.jcis.2020.10.101

Cited by 28 publications

(22 citation statements)

References 94 publications

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“…The morphology and structure of mixed micelles have been recently analyzed by scattering techniques and atomistic simulations. 52 Larger micelles are formed with long fatty acids than with short fatty acids. It is then possible that larger micelles could be formed with nonpolar chlorophylls that carry a phytol chain (C 20 H 20 ), which is not present in polar chlorophylls (pheophorbides).…”

Section: Resultsmentioning

confidence: 99%

In Vitro Bioaccessibility Protocol for Chlorophylls

Viera

Herrera

Roca

2021

J. Agric. Food Chem.

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The daily ingestion of chlorophylls has been estimated at 50 g, but the knowledge about their bioaccessibility is limited. Different in vitro models have been utilized to estimate their potential bioavailability, but among other factors, the diversity of structures, chemical properties, and lability of chlorophylls hamper the investigations. By the first time, three extreme food matrices, one rich in fiber (vegetable puree), one rich in fat (virgin olive oil), and one liquid (fruit juice), have been assayed for chlorophyll bioaccessibility, controlling crucial variables. Chlorophyll polarity and food matrix were the determining factors, but surprisingly, chlorophyll bioaccessibility was affected during the application of the in vitro standardized protocol. Therefore, the present research has identified the reactions that can be biased during the estimation of chlorophyll bioaccessibility, defining a specific protocol in the function of chlorophyll structures.

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Section: Resultsmentioning

confidence: 99%

In Vitro Bioaccessibility Protocol for Chlorophylls

Viera

Herrera

Roca

2021

J. Agric. Food Chem.

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“…deuterated molecules are highlighted in H 2 O and hydrogenous molecules are highlighted in D 2 O [16][17][18]. In the context of digestion, SANS has been applied most extensively in studying the interaction of simulated intestinal fluids (bile salt/phospholipid mixed micelles and vesicles) with digestive enzymes or simulated digestion product mixtures [19][20][21][22]. The main drawback of neutron scattering is the inherently lower radiation flux of neutron sources when compared with synchrotron light sources.…”

Section: Complementary Techniques For Studying the Structural Evolution Of Lipids During Digestionmentioning

confidence: 99%

“…This increases the typical acquisition time required for data collection, which thereby reduces the temporal resolution of time-resolved neutron studies relative to synchrotron X-ray measurements. For this reason, many neutron scattering studies are not in situ time-resolved measurements of the evolving sample but are ex situ steady-state measurements on simulated digesting mixtures [ 19 , 22 ] or those in which the lipase has been inhibited by the addition of an alcoholic inhibitor solution [ 21 ]. Solutions to the issue of temporal resolution include improving detector efficiency [ 23 ] and the more widespread use of time-of-flight SANS (TOF-SANS) instruments.…”

Section: Introductionmentioning

confidence: 99%

“…To maintain the simplicity of the models, where lipid digestion products are introduced in the simulations often only a single representative lipid chain length or digestion product is introduced [ 20 , 27 , 31 ], rather than the more complex lipid mixtures typically encountered in lipid-based formulations. Nonetheless, MD simulations have been combined with both SAXS [ 19 , 32 ] and SANS [ 19 , 20 ] analyses to support structural models of intestinal fluids during digestion.…”

Section: Introductionmentioning

confidence: 99%

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The influence of lipid digestion on the fate of orally administered drug delivery vehicles

Boyd

2021

Biochemical Society Transactions

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This review will focus on orally administered lipid-based drug delivery vehicles and specifically the influence of lipid digestion on the structure of the carrier lipids and their entrained drug cargoes. Digestion of the formulation lipids, which are typically apolar triglycerides, generates amphiphilic monoglycerides and fatty acids that can self-assemble into a diverse array of liquid crystalline structures. Tracking the dynamic changes in self-assembly of the lipid digestion products during digestion has recently been made possible using synchrotron-based small angle X-ray scattering. The influence of lipid chain length and degree of unsaturation on the resulting lipid structuring will be described in the context of the critical packing parameter theory. The chemical and structural transformation of the formulation lipids can also have a dramatic impact on the physical state of drugs co-administered with the formulation. It is often assumed that the best strategy for drug development is to maximise drug solubility in the undigested formulation lipids and to incorporate additives to maintain drug solubility during digestion. However, it is possible to improve drug absorption using lipid digestion in cases where the solubility of the dosed drug or one of its polymorphic forms is greater in the digested lipids. Three different fates for drugs administered with digestible lipid-based formulations will be discussed: (1) where the drug is more soluble in the undigested formulation lipids; (2) where the drug undergoes a polymorphic transformation during lipid digestion; and (3) where the drug is more soluble in the digested formulation lipids.

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“…Digestion therefore represents a critical step in lipid-based drug delivery as lipases, in particular human pancreatic lipase, hydrolyse triacylglycerols (TAGs) in formulations to produce more polar lipid species, 2-monoacylglycerols (2-MAGs) and fatty acids (FAs) ( Jannin et al, 2015 ; Bakala N'Goma et al, 2012 ). These amphiphilic digestion products can self-assemble into lyotropic liquid crystalline structures in the small intestine ( Salentinig et al, 2013 , Salentinig et al, 2015 ; Clulow et al, 2018 ; Pham et al, 2020 ), in turn these structures interact with endogenous amphiphilic molecules such as bile acids to form colloidal mixed micelles with a variety of structures ( Hjelm et al, 2000 ; Hjelm et al, 1995 ; Pabois et al, 2021 ; Rezhdo et al, 2017 ; Gustafsson et al, 1999 ; Clulow et al, 2017 ). The digestion products are also capable of solubilising poorly water-soluble drugs dispersed in the LBF ( Shrestha et al, 2014 ; Salim et al, 2019a ; Boyd et al, 2018 ; Salim et al, 2020a ) making them available for subsequent absorption ( Tan et al, 2010 ; Borné et al, 2002 ; Boyd et al, 2007 ).…”

Section: Introductionmentioning

confidence: 99%