-
Something wrong with this record ?
Esters of terpene alcohols as highly potent, reversible, and low toxic skin penetration enhancers
M. Kopečná, M. Macháček, A. Nováčková, G. Paraskevopoulos, J. Roh, K. Vávrová,
Language English Country Great Britain
Document type Journal Article, Research Support, Non-U.S. Gov't
NLK
Directory of Open Access Journals
from 2011
Free Medical Journals
from 2011
Nature Open Access
from 2011-12-01
PubMed Central
from 2011
Europe PubMed Central
from 2011
ProQuest Central
from 2011-01-01
Open Access Digital Library
from 2011-01-01
Open Access Digital Library
from 2011-01-01
Health & Medicine (ProQuest)
from 2011-01-01
ROAD: Directory of Open Access Scholarly Resources
from 2011
Springer Nature OA/Free Journals
from 2011-12-01
- MeSH
- Alcohols chemistry pharmacology MeSH
- Administration, Cutaneous MeSH
- 3T3 Cells MeSH
- Cidofovir administration & dosage chemistry pharmacokinetics MeSH
- Epidermis drug effects metabolism MeSH
- Esters chemistry pharmacology MeSH
- Chemistry, Pharmaceutical MeSH
- Pharmaceutic Aids chemistry pharmacology MeSH
- Hydrocortisone administration & dosage chemistry pharmacokinetics MeSH
- Keratinocytes MeSH
- Humans MeSH
- Lipid Metabolism drug effects MeSH
- Monoterpenes chemistry MeSH
- Mice MeSH
- Permeability drug effects MeSH
- Water Loss, Insensible drug effects MeSH
- Drug Compounding methods MeSH
- Terpenes chemistry pharmacology MeSH
- Toxicity Tests, Acute MeSH
- Theophylline administration & dosage chemistry pharmacokinetics MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
Skin penetration/permeation enhancers are compounds that improve (trans)dermal drug delivery. We designed hybrid terpene-amino acid enhancers by conjugating natural terpenes (citronellol, geraniol, nerol, farnesol, linalool, perillyl alcohol, menthol, borneol, carveol) or cinnamyl alcohol with 6-(dimethylamino)hexanoic acid through a biodegradable ester linker. The compounds were screened for their ability to increase the delivery of theophylline and hydrocortisone through and into human skin ex vivo. The citronellyl, bornyl and cinnamyl esters showed exceptional permeation-enhancing properties (enhancement ratios up to 82) while having low cellular toxicities. The barrier function of enhancer-treated skin (assessed by transepidermal water loss and electrical impedance) recovered within 24 h. Infrared spectroscopy suggested that these esters fluidized the stratum corneum lipids. Furthermore, the citronellyl ester increased the epidermal concentration of topically applied cidofovir, which is a potent antiviral and anticancer drug, by 15-fold. In conclusion, citronellyl 6-(dimethylamino)hexanoate is an outstanding enhancer with an advantageous combination of properties, which may improve the delivery of drugs that have a limited ability to cross biological barriers.
References provided by Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc20028793
- 003
- CZ-PrNML
- 005
- 20210322090755.0
- 007
- ta
- 008
- 210105s2019 xxk f 000 0|eng||
- 009
- AR
- 024 7_
- $a 10.1038/s41598-019-51226-5 $2 doi
- 035 __
- $a (PubMed)31601936
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a xxk
- 100 1_
- $a Kopečná, Monika $u Skin Barrier Research Group, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
- 245 10
- $a Esters of terpene alcohols as highly potent, reversible, and low toxic skin penetration enhancers / $c M. Kopečná, M. Macháček, A. Nováčková, G. Paraskevopoulos, J. Roh, K. Vávrová,
- 520 9_
- $a Skin penetration/permeation enhancers are compounds that improve (trans)dermal drug delivery. We designed hybrid terpene-amino acid enhancers by conjugating natural terpenes (citronellol, geraniol, nerol, farnesol, linalool, perillyl alcohol, menthol, borneol, carveol) or cinnamyl alcohol with 6-(dimethylamino)hexanoic acid through a biodegradable ester linker. The compounds were screened for their ability to increase the delivery of theophylline and hydrocortisone through and into human skin ex vivo. The citronellyl, bornyl and cinnamyl esters showed exceptional permeation-enhancing properties (enhancement ratios up to 82) while having low cellular toxicities. The barrier function of enhancer-treated skin (assessed by transepidermal water loss and electrical impedance) recovered within 24 h. Infrared spectroscopy suggested that these esters fluidized the stratum corneum lipids. Furthermore, the citronellyl ester increased the epidermal concentration of topically applied cidofovir, which is a potent antiviral and anticancer drug, by 15-fold. In conclusion, citronellyl 6-(dimethylamino)hexanoate is an outstanding enhancer with an advantageous combination of properties, which may improve the delivery of drugs that have a limited ability to cross biological barriers.
- 650 _2
- $a buňky 3T3 $7 D016475
- 650 _2
- $a aplikace kožní $7 D000279
- 650 _2
- $a alkoholy $x chemie $x farmakologie $7 D000438
- 650 _2
- $a zvířata $7 D000818
- 650 _2
- $a farmaceutická chemie $7 D002626
- 650 _2
- $a cidofovir $x aplikace a dávkování $x chemie $x farmakokinetika $7 D000077404
- 650 _2
- $a příprava léků $x metody $7 D004339
- 650 _2
- $a epidermis $x účinky léků $x metabolismus $7 D004817
- 650 _2
- $a estery $x chemie $x farmakologie $7 D004952
- 650 _2
- $a lidé $7 D006801
- 650 _2
- $a hydrokortison $x aplikace a dávkování $x chemie $x farmakokinetika $7 D006854
- 650 _2
- $a keratinocyty $7 D015603
- 650 _2
- $a metabolismus lipidů $x účinky léků $7 D050356
- 650 _2
- $a myši $7 D051379
- 650 _2
- $a monoterpeny $x chemie $7 D039821
- 650 _2
- $a permeabilita $x účinky léků $7 D010539
- 650 _2
- $a farmaceutické pomocné látky $x chemie $x farmakologie $7 D010592
- 650 _2
- $a vztahy mezi strukturou a aktivitou $7 D013329
- 650 _2
- $a terpeny $x chemie $x farmakologie $7 D013729
- 650 _2
- $a theofylin $x aplikace a dávkování $x chemie $x farmakokinetika $7 D013806
- 650 _2
- $a testy akutní toxicity $7 D023382
- 650 _2
- $a perspiratio insensibilis $x účinky léků $7 D014870
- 655 _2
- $a časopisecké články $7 D016428
- 655 _2
- $a práce podpořená grantem $7 D013485
- 700 1_
- $a Macháček, Miloslav $u Department of Biochemical Sciences, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
- 700 1_
- $a Nováčková, Anna $u Skin Barrier Research Group, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
- 700 1_
- $a Paraskevopoulos, Georgios, $u Skin Barrier Research Group, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic. $d 1981- $7 uk20201094683
- 700 1_
- $a Roh, Jaroslav $u Department of Organic and Bioorganic Chemistry, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic.
- 700 1_
- $a Vávrová, Kateřina $u Skin Barrier Research Group, Charles University, Faculty of Pharmacy in Hradec Králové, Akademika Heyrovského 1203, 50005, Hradec Králové, Czech Republic. katerina.vavrova@faf.cuni.cz.
- 773 0_
- $w MED00182195 $t Scientific reports $x 2045-2322 $g Roč. 9, č. 1 (2019), s. 14617
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/31601936 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y a $z 0
- 990 __
- $a 20210105 $b ABA008
- 991 __
- $a 20210322090710 $b ABA008
- 999 __
- $a ok $b bmc $g 1609128 $s 1119973
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2019 $b 9 $c 1 $d 14617 $e 20191010 $i 2045-2322 $m Scientific reports $n Sci Rep $x MED00182195
- LZP __
- $a Pubmed-20210105
