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Synthesis, physico-chemical properties and penetration activity of alkyl-6-(2,5-dioxopyrrolidin-1-yl)-2-(2-oxopyrrolidin-1-yl)hexanoates as potential transdermal penetration enhancers.
- Source :
-
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2010 Jan 01; Vol. 18 (1), pp. 73-9. Date of Electronic Publication: 2009 Nov 12. - Publication Year :
- 2010
-
Abstract
- Skin penetration enhancers are used to allow formulation of transdermal delivery systems for drugs that are otherwise insufficiently skin-permeable. The series of seven esters of substituted 6-aminohexanoic acid as potential transdermal penetration enhancers was formed by multistep synthesis. The synthesis of all newly prepared compounds is presented here. Structure confirmation of all generated compounds was accomplished by (1)H NMR, (13)C NMR, IR and MS spectroscopy. All the prepared compounds were analyzed using RP-HPLC method for the lipophilicity measurement and their lipophilicity (logk) was determined. Hydrophobicities (logP/ClogP) of the studied compounds were also calculated using two commercially available programs and 3D structures of the selected compounds were investigated by means of ab initio/DFT calculations of geometry. All the synthesized esters were tested for their in vitro transdermal penetration enhancer activity. The relationships between the lipophilicity and the chemical structure (SLR) of the studied compounds as well as the relationships between their chemical structure and transdermal penetration activity are mentioned.<br /> (Copyright (c) 2009 Elsevier Ltd. All rights reserved.)
- Subjects :
- Administration, Cutaneous
Animals
Lipids chemistry
Models, Molecular
Molecular Conformation
Permeability drug effects
Skin drug effects
Skin metabolism
Swine
Theophylline pharmacokinetics
Aminocaproic Acid chemistry
Aminocaproic Acid pharmacology
Drug Carriers chemistry
Drug Carriers pharmacology
Skin Absorption drug effects
Theophylline administration & dosage
Subjects
Details
- Language :
- English
- ISSN :
- 1464-3391
- Volume :
- 18
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Bioorganic & medicinal chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 19954983
- Full Text :
- https://doi.org/10.1016/j.bmc.2009.11.020