Effect of ion-pairing on 1-octanol-water partitioning of peptide drugs. I: The nonapeptide leuprolide acetate

Adjei, Akwete; Rao, Sumati; Garren, J.; Vadnere, Madhu

doi:10.1016/0378-5173(93)90150-e

Cited by 27 publications

(22 citation statements)

References 15 publications

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“…Interest in HIPs has been increasing in the field of drug delivery as they transform hydrophilic molecules and ions into lipophilic structures resulting in the formation of supramolecular species (6)(7)(8)(9). The formation of HIPs results in shielding of ionic charges from solvents and alteration of properties such as solubility (1,3), extraction coefficients (3,10,11) and stability (1,11). Encapsulation efficiency is also improved and the undesirable burst effect is minimised (1,5,12).…”

Section: Introductionmentioning

confidence: 96%

Chlorhexidine/losartan ionic pair binding and its nanoprecipitation: physico-chemical characterisation and antimicrobial activity

Denadai

Oliveira

Daniel

et al. 2011

Supramolecular Chemistry

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Chlorhexidine is a widely used, di-cationic, broad-spectrum antimicrobial agent and losartan is a well-known, anionic-specific antagonist of AT1 renin-angiotensin receptor that acts as an anti-hypertensive agent. The combination of these molecules gives a chlorhexidine di-losartanate (ClxLos 2 ) hydrophobic ion pair that spontaneously aggregates into nanoparticles (NPs). This work investigated the formation of ClxLos 2 NPs using the analysis of the solid state by fourier transform infrared spectroscopy, thermogravimetric analysis, differential scanning calorimetry and scanning electron microscopy and in aqueous environment by calorimetric, zeta potential and dynamic light scattering titrations. Furthermore, to demonstrate the potential antimicrobial activity of ClxLos 2 , in vitro antibacterial tests were conducted against Staphylococcus aureus (ATCC 27664), Streptococcus viridans (ATCC 11563) and Enterococcus faecalis (ATCC 14508). Based on these studies, it is proposed that ClxLos 2 could be used for controlled drug release based on ionic dissociation during dilution, thereby avoiding the use of any solid matrix.

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Section: Introductionmentioning

confidence: 96%

Chlorhexidine/losartan ionic pair binding and its nanoprecipitation: physico-chemical characterisation and antimicrobial activity

Denadai

Oliveira

Daniel

et al. 2011

Supramolecular Chemistry

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“…It was reported that a hydrophobic ion pairing (HIP) method had been used to enhance the hydrophobicity of protein/peptides (Adjei et al 1993;Matsuura et al 1993;Meyer and Manning 1998). In order to encapsulate more insulin in the hydrophobic copolymer, the hydrophobic ion pairing (HIP) technique has been applied to prepare Ins-S.O complex to enhance the hydrophobicity of insulin in our previous work (Sun et al 2008).…”

Section: Introductionmentioning

confidence: 98%

Insulin-S.O (sodium oleate) complex-loaded PLGA nanoparticles: Formulation, characterization andin vivoevaluation

Sun

Liang

Piao

et al. 2010

Journal of Microencapsulation

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S.O (sodium oleate) is an anionic surfactant, which is able to forman ionic complex with positively charged insulin at suitable pH. In a previous study, the insulin-S.O (Ins-S.O) complex was prepared by a hydrophobic ion pairing (HIP) method to improve the apparent liposolubility of insulin. The formation of the complex was further confirmed by Zeta potential and X-ray method. Based on the preliminary study, poly(lactide-co-glycolide) (PLGA) nanoparticles harbouring Ins-S.O complex was prepared via an emulsion solvent diffusion method. The effects of key parameters such as concentration of PVA, concentration of PLGA and initial-loaded drug on the properties of the nanoparticles were investigated. The insulin encapsulation efficiency (EE(%)) reached up to 91.2% and mean diameter of the nanoparticles was sized approximately 160 nm under optimal conditions. The pharmacological effects of the nanoparticles made of PLGA (75/25, Av Mw 15,000) were further evaluated to confirm their potential suitability for oral delivery. In order to evaluate hyperglycaemic effect of the nanoparticles for oral administration, Ins-S.O complex-loaded PLGA nanoparticles (20 IU/Kg) were administered orally by force-feeding to diabetic rats. In the case of the nanoparticles, the plasma glucose level reduced to 23.85% from the initial one 12 h post-administration and this continued for 24 h. The results showed that the use of Ins-S.O complex-loaded PLGA nanoparticles is an effective method of reducing plasma glucose levels. The insulin nanoparticles also improved the glycaemic response to an oral glucose challenge.

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“…Major advantage of hydrophobic ion-pairing is to increase the lipophilicity of hydrophilic molecules [17,19]. Another strategy has also been developed for the separation of peptides or proteins by ionic-pairing with amphipathic molecules [20][21][22][23]. Hydrophobically modified peptides or proteins allowed the increase of their extraction in organic solvent.…”

Section: Introductionmentioning

confidence: 98%

Ion-pairing separation of bioactive peptides using an aqueous/octan-1-ol micro-extraction system from bovine haemoglobin complex hydrolysates

Vanhoute¹,

Froidevaux²,

Vanvlassenbroeck³

et al. 2009

Journal of Chromatography B

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Effect of ion-pairing on 1-octanol-water partitioning of peptide drugs. I: The nonapeptide leuprolide acetate

Cited by 27 publications

References 15 publications

Chlorhexidine/losartan ionic pair binding and its nanoprecipitation: physico-chemical characterisation and antimicrobial activity

Chlorhexidine/losartan ionic pair binding and its nanoprecipitation: physico-chemical characterisation and antimicrobial activity

Insulin-S.O (sodium oleate) complex-loaded PLGA nanoparticles: Formulation, characterization andin vivoevaluation

Ion-pairing separation of bioactive peptides using an aqueous/octan-1-ol micro-extraction system from bovine haemoglobin complex hydrolysates

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