Characterization of phospholipid vesicles containing lauric acid: physicochemical basis for process and product development

Laura Farkuh; Paulo T. Hennies; Cláudia Nunes; Salette Reis; Luisa Barreiros; Marcela A. Segundo; Pedro L. Oseliero Filho; Cristiano L.P. Oliveira; Alexandre Cassago; Rodrigo V. Portugal; Rodrigo A. Muramoto; Gustavo P.B. Carretero; Shirley Schreier; Hernan Chaimovich; Iolanda M. Cuccovia

doi:10.1016/j.heliyon.2019.e02648

Characterization of phospholipid vesicles containing lauric acid: physicochemical basis for process and product development

Laura Farkuh, Paulo T. Hennies, Cláudia Nunes, Salette Reis, Luisa Barreiros, Marcela A. Segundo, Pedro L. Oseliero Filho, Cristiano L.P. Oliveira, Alexandre Cassago, Rodrigo V. Portugal, Rodrigo A. Muramoto, Gustavo P.B. Carretero, Shirley Schreier, Hernan Chaimovich, Iolanda M. Cuccovia^*

^*Corresponding author

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

Abstract

Lauric acid (LAH) strongly inhibits the growth of acne-causing bacteria. LAH is essentially water-insoluble and the solubility of laurate (LA) salts are medium and temperature dependent. Hence, LAH/LA preparations are difficult to formulate. Here we fully characterized phospholipid vesicles containing up to 50 mol% LAH. Vesicles of dipalmitoylphosphatidylcholine (DPPC) containing LAH, at pHs 7.4 and 5.0, were characterized measuring size, charge, bilayer phase transition temperature (Tm) and permeability of water-soluble probes. Small angle X-ray scattering and cryotransmission electron microscopy showed multilamellar vesicles at low LAH %. Increasing LAH % had a negligible effect on particle size. An internal aqueous compartment in all vesicle's preparations, even at equimolar DPPC: LAH fractions, was demonstrated using water-soluble probes. At pH 5.0, the interaction between DPPC and LAH increased the Tm and phase transition cooperativity showing a single lipid phase formed by hydrogen-bonded DPPC: LAH complexes. At pH 7.4, vesicles containing 50 mol% LAH exhibited distinct phases, ascribed to complex formation between LAH and LA or LAH and DPPC. LAH incorporated in the vesicles minimally permeated a skin preparation at both pHs, indicating that the primary sites of LAH solubilization were the skin layers. These results provide the foundations for developing processes and products containing DPPC: LAH.

Originalsprog	Engelsk
Artikelnummer	e02648
Tidsskrift	Heliyon
Vol/bind	5
Udgave nummer	10
Antal sider	10
ISSN	2405-8440
DOI	https://doi.org/10.1016/j.heliyon.2019.e02648
Status	Udgivet - okt. 2019
Udgivet eksternt	Ja

Bibliografisk note

Funding Information:
L. Farkuh thanks Ph.D. Bárbara Bianca Gerbelli (IF-USP), CNPq, FAPESP (Proc. 2013/08166-5), Santander Universidades (COPGRAD.01 - 044/2014). I.M.Cuccovia thanks the National Council for Scientific and Technological Development (CNPq – 465259/2014-6), the Coordination for the Improvement of Higher Education Personnel (CAPES), the National Institute of Science and Technology Complex Fluids (INCT-FCx), and the São Paulo Research Foundation (FAPESP – 2014/50983-3). We acknowledge the Brazilian Nanotechnology National Laboratory (LNNano), CNPEM, for the use of cryo-TEM facilities. This work was supported by The European Union ( FEDER funds) and National Funds ( FCT / MEC , Fundação para a Ciência e a Tecnologia and Ministério da Educação e Ciência) under the Partnership Agreement PT2020 UID/QUI/50006/2013 - POCI/01/0145/FEDER/007265. L. Barreiros thanks FCT and POPH (Programa Operacional Potencial Humano) for her Post-Doc grant (SFRH/BPD/89668/2012). C. Nunes thanks FCT for her Investigator Grant (IF/00293/2015). G.P.B.Carretero acknowledges the Programa CAPES: INCT -Institutos Nacionais de Ciência e Tecnologia (Proc. 88887.137085/2017-00), R.A. Muramoto acknowledges CNPq. I.M. Cuccovia, H. Chaimovich, and S. Schreier are research fellows of CNPq.

Emneord

Biotechnology
Cryo-TEM
DLS
DSC
Ionizable solute
Lauric acid
Lipid Vesicles
Pharmaceutical Science
SAXS

Link til dokument

10.1016/j.heliyon.2019.e02648Licens: CC BY

Characterization of phospholipid vesicles containing lauric acid: physicochemical basis for process and product developmentForlagets udgivne version, 2,04 MBLicens: CC BY

Citer dette

Farkuh, L., Hennies, P. T., Nunes, C., Reis, S., Barreiros, L., Segundo, M. A., Oseliero Filho, P. L., Oliveira, C. L. P., Cassago, A., Portugal, R. V., Muramoto, R. A., Carretero, G. P. B., Schreier, S., Chaimovich, H., & Cuccovia, I. M. (2019). Characterization of phospholipid vesicles containing lauric acid: physicochemical basis for process and product development. Heliyon, 5(10), Artikel e02648. https://doi.org/10.1016/j.heliyon.2019.e02648

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title = "Characterization of phospholipid vesicles containing lauric acid: physicochemical basis for process and product development",

abstract = "Lauric acid (LAH) strongly inhibits the growth of acne-causing bacteria. LAH is essentially water-insoluble and the solubility of laurate (LA) salts are medium and temperature dependent. Hence, LAH/LA preparations are difficult to formulate. Here we fully characterized phospholipid vesicles containing up to 50 mol% LAH. Vesicles of dipalmitoylphosphatidylcholine (DPPC) containing LAH, at pHs 7.4 and 5.0, were characterized measuring size, charge, bilayer phase transition temperature (Tm) and permeability of water-soluble probes. Small angle X-ray scattering and cryotransmission electron microscopy showed multilamellar vesicles at low LAH %. Increasing LAH % had a negligible effect on particle size. An internal aqueous compartment in all vesicle's preparations, even at equimolar DPPC: LAH fractions, was demonstrated using water-soluble probes. At pH 5.0, the interaction between DPPC and LAH increased the Tm and phase transition cooperativity showing a single lipid phase formed by hydrogen-bonded DPPC: LAH complexes. At pH 7.4, vesicles containing 50 mol% LAH exhibited distinct phases, ascribed to complex formation between LAH and LA or LAH and DPPC. LAH incorporated in the vesicles minimally permeated a skin preparation at both pHs, indicating that the primary sites of LAH solubilization were the skin layers. These results provide the foundations for developing processes and products containing DPPC: LAH.",

keywords = "Biotechnology, Cryo-TEM, DLS, DSC, Ionizable solute, Lauric acid, Lipid Vesicles, Pharmaceutical Science, SAXS, Biotechnology, Cryo-TEM, DLS, DSC, Ionizable solute, Lauric acid, Lipid Vesicles, Pharmaceutical Science, SAXS",

author = "Laura Farkuh and Hennies, {Paulo T.} and Cl{\'a}udia Nunes and Salette Reis and Luisa Barreiros and Segundo, {Marcela A.} and {Oseliero Filho}, {Pedro L.} and Oliveira, {Cristiano L.P.} and Alexandre Cassago and Portugal, {Rodrigo V.} and Muramoto, {Rodrigo A.} and Carretero, {Gustavo P.B.} and Shirley Schreier and Hernan Chaimovich and Cuccovia, {Iolanda M.}",

note = "Funding Information: L. Farkuh thanks Ph.D. B{\'a}rbara Bianca Gerbelli (IF-USP), CNPq, FAPESP (Proc. 2013/08166-5), Santander Universidades (COPGRAD.01 - 044/2014). I.M.Cuccovia thanks the National Council for Scientific and Technological Development (CNPq – 465259/2014-6), the Coordination for the Improvement of Higher Education Personnel (CAPES), the National Institute of Science and Technology Complex Fluids (INCT-FCx), and the S{\~a}o Paulo Research Foundation (FAPESP – 2014/50983-3). We acknowledge the Brazilian Nanotechnology National Laboratory (LNNano), CNPEM, for the use of cryo-TEM facilities. This work was supported by The European Union ( FEDER funds) and National Funds ( FCT / MEC , Funda{\c c}{\~a}o para a Ci{\^e}ncia e a Tecnologia and Minist{\'e}rio da Educa{\c c}{\~a}o e Ci{\^e}ncia) under the Partnership Agreement PT2020 UID/QUI/50006/2013 - POCI/01/0145/FEDER/007265. L. Barreiros thanks FCT and POPH (Programa Operacional Potencial Humano) for her Post-Doc grant (SFRH/BPD/89668/2012). C. Nunes thanks FCT for her Investigator Grant (IF/00293/2015). G.P.B.Carretero acknowledges the Programa CAPES: INCT -Institutos Nacionais de Ci{\^e}ncia e Tecnologia (Proc. 88887.137085/2017-00), R.A. Muramoto acknowledges CNPq. I.M. Cuccovia, H. Chaimovich, and S. Schreier are research fellows of CNPq. ",

year = "2019",

month = oct,

doi = "10.1016/j.heliyon.2019.e02648",

language = "English",

volume = "5",

journal = "Heliyon",

issn = "2405-8440",

publisher = "Elsevier Ltd",

number = "10",

}

Farkuh, L, Hennies, PT, Nunes, C, Reis, S, Barreiros, L, Segundo, MA, Oseliero Filho, PL, Oliveira, CLP, Cassago, A, Portugal, RV, Muramoto, RA, Carretero, GPB, Schreier, S, Chaimovich, H & Cuccovia, IM 2019, 'Characterization of phospholipid vesicles containing lauric acid: physicochemical basis for process and product development', Heliyon, bind 5, nr. 10, e02648. https://doi.org/10.1016/j.heliyon.2019.e02648

TY - JOUR

T1 - Characterization of phospholipid vesicles containing lauric acid

T2 - physicochemical basis for process and product development

AU - Farkuh, Laura

AU - Hennies, Paulo T.

AU - Nunes, Cláudia

AU - Reis, Salette

AU - Barreiros, Luisa

AU - Segundo, Marcela A.

AU - Oseliero Filho, Pedro L.

AU - Oliveira, Cristiano L.P.

AU - Cassago, Alexandre

AU - Portugal, Rodrigo V.

AU - Muramoto, Rodrigo A.

AU - Carretero, Gustavo P.B.

AU - Schreier, Shirley

AU - Chaimovich, Hernan

AU - Cuccovia, Iolanda M.

N1 - Funding Information: L. Farkuh thanks Ph.D. Bárbara Bianca Gerbelli (IF-USP), CNPq, FAPESP (Proc. 2013/08166-5), Santander Universidades (COPGRAD.01 - 044/2014). I.M.Cuccovia thanks the National Council for Scientific and Technological Development (CNPq – 465259/2014-6), the Coordination for the Improvement of Higher Education Personnel (CAPES), the National Institute of Science and Technology Complex Fluids (INCT-FCx), and the São Paulo Research Foundation (FAPESP – 2014/50983-3). We acknowledge the Brazilian Nanotechnology National Laboratory (LNNano), CNPEM, for the use of cryo-TEM facilities. This work was supported by The European Union ( FEDER funds) and National Funds ( FCT / MEC , Fundação para a Ciência e a Tecnologia and Ministério da Educação e Ciência) under the Partnership Agreement PT2020 UID/QUI/50006/2013 - POCI/01/0145/FEDER/007265. L. Barreiros thanks FCT and POPH (Programa Operacional Potencial Humano) for her Post-Doc grant (SFRH/BPD/89668/2012). C. Nunes thanks FCT for her Investigator Grant (IF/00293/2015). G.P.B.Carretero acknowledges the Programa CAPES: INCT -Institutos Nacionais de Ciência e Tecnologia (Proc. 88887.137085/2017-00), R.A. Muramoto acknowledges CNPq. I.M. Cuccovia, H. Chaimovich, and S. Schreier are research fellows of CNPq.

PY - 2019/10

Y1 - 2019/10

N2 - Lauric acid (LAH) strongly inhibits the growth of acne-causing bacteria. LAH is essentially water-insoluble and the solubility of laurate (LA) salts are medium and temperature dependent. Hence, LAH/LA preparations are difficult to formulate. Here we fully characterized phospholipid vesicles containing up to 50 mol% LAH. Vesicles of dipalmitoylphosphatidylcholine (DPPC) containing LAH, at pHs 7.4 and 5.0, were characterized measuring size, charge, bilayer phase transition temperature (Tm) and permeability of water-soluble probes. Small angle X-ray scattering and cryotransmission electron microscopy showed multilamellar vesicles at low LAH %. Increasing LAH % had a negligible effect on particle size. An internal aqueous compartment in all vesicle's preparations, even at equimolar DPPC: LAH fractions, was demonstrated using water-soluble probes. At pH 5.0, the interaction between DPPC and LAH increased the Tm and phase transition cooperativity showing a single lipid phase formed by hydrogen-bonded DPPC: LAH complexes. At pH 7.4, vesicles containing 50 mol% LAH exhibited distinct phases, ascribed to complex formation between LAH and LA or LAH and DPPC. LAH incorporated in the vesicles minimally permeated a skin preparation at both pHs, indicating that the primary sites of LAH solubilization were the skin layers. These results provide the foundations for developing processes and products containing DPPC: LAH.

AB - Lauric acid (LAH) strongly inhibits the growth of acne-causing bacteria. LAH is essentially water-insoluble and the solubility of laurate (LA) salts are medium and temperature dependent. Hence, LAH/LA preparations are difficult to formulate. Here we fully characterized phospholipid vesicles containing up to 50 mol% LAH. Vesicles of dipalmitoylphosphatidylcholine (DPPC) containing LAH, at pHs 7.4 and 5.0, were characterized measuring size, charge, bilayer phase transition temperature (Tm) and permeability of water-soluble probes. Small angle X-ray scattering and cryotransmission electron microscopy showed multilamellar vesicles at low LAH %. Increasing LAH % had a negligible effect on particle size. An internal aqueous compartment in all vesicle's preparations, even at equimolar DPPC: LAH fractions, was demonstrated using water-soluble probes. At pH 5.0, the interaction between DPPC and LAH increased the Tm and phase transition cooperativity showing a single lipid phase formed by hydrogen-bonded DPPC: LAH complexes. At pH 7.4, vesicles containing 50 mol% LAH exhibited distinct phases, ascribed to complex formation between LAH and LA or LAH and DPPC. LAH incorporated in the vesicles minimally permeated a skin preparation at both pHs, indicating that the primary sites of LAH solubilization were the skin layers. These results provide the foundations for developing processes and products containing DPPC: LAH.

KW - Biotechnology

KW - Cryo-TEM

KW - DLS

KW - DSC

KW - Ionizable solute

KW - Lauric acid

KW - Lipid Vesicles

KW - Pharmaceutical Science

KW - SAXS

KW - Biotechnology

KW - Cryo-TEM

KW - DLS

KW - DSC

KW - Ionizable solute

KW - Lauric acid

KW - Lipid Vesicles

KW - Pharmaceutical Science

KW - SAXS

U2 - 10.1016/j.heliyon.2019.e02648

DO - 10.1016/j.heliyon.2019.e02648

M3 - Journal article

AN - SCOPUS:85074055157

SN - 2405-8440

VL - 5

JO - Heliyon

JF - Heliyon

IS - 10

M1 - e02648

ER -