Types of interaction of amphiphilic drugs with phospholipid vesicles.
Identifieur interne : 003185 ( Main/Exploration ); précédent : 003184; suivant : 003186Types of interaction of amphiphilic drugs with phospholipid vesicles.
Auteurs : U M Joshi ; P R Kodavanti ; B. Coudert ; T M Dwyer ; H M MehendaleSource :
- The Journal of pharmacology and experimental therapeutics [ 0022-3565 ] ; 1988.
Descripteurs français
- KwdFr :
- 1,6-Diphényl-hexa-1,3,5-triène, Amiodarone (effets indésirables), Amiodarone (métabolisme), Anilino-naphtalènesulfonates, Chloramphénicol (effets indésirables), Chloramphénicol (métabolisme), Chloroquine (effets indésirables), Chloroquine (métabolisme), Chlorpromazine (effets indésirables), Chlorpromazine (métabolisme), Imipramine (effets indésirables), Imipramine (métabolisme), Lipides membranaires (métabolisme), Lipidoses (), Maladies pulmonaires (), Phospholipides (métabolisme), Prométhazine (effets indésirables), Prométhazine (métabolisme), Propranolol (effets indésirables), Propranolol (métabolisme), Sites de fixation, Tensioactifs (effets indésirables), Tensioactifs (métabolisme), Trimipramine (effets indésirables), Trimipramine (métabolisme).
- MESH :
- effets indésirables : Amiodarone, Chloramphénicol, Chloroquine, Chlorpromazine, Imipramine, Prométhazine, Propranolol, Tensioactifs, Trimipramine.
- métabolisme : Amiodarone, Chloramphénicol, Chloroquine, Chlorpromazine, Imipramine, Lipides membranaires, Phospholipides, Prométhazine, Propranolol, Tensioactifs, Trimipramine.
- 1,6-Diphényl-hexa-1,3,5-triène, Anilino-naphtalènesulfonates, Lipidoses, Maladies pulmonaires, Sites de fixation.
English descriptors
- KwdEn :
- Amiodarone (adverse effects), Amiodarone (metabolism), Anilino Naphthalenesulfonates, Binding Sites, Chloramphenicol (adverse effects), Chloramphenicol (metabolism), Chloroquine (adverse effects), Chloroquine (metabolism), Chlorpromazine (adverse effects), Chlorpromazine (metabolism), Diphenylhexatriene, Imipramine (adverse effects), Imipramine (metabolism), Lipidoses (chemically induced), Lung Diseases (chemically induced), Membrane Lipids (metabolism), Phospholipids (metabolism), Promethazine (adverse effects), Promethazine (metabolism), Propranolol (adverse effects), Propranolol (metabolism), Surface-Active Agents (adverse effects), Surface-Active Agents (metabolism), Trimipramine (adverse effects), Trimipramine (metabolism).
- MESH :
- chemical , adverse effects : Amiodarone, Chloramphenicol, Chloroquine, Chlorpromazine, Imipramine, Promethazine, Propranolol, Surface-Active Agents, Trimipramine.
- chemical , metabolism : Amiodarone, Chloramphenicol, Chloroquine, Chlorpromazine, Imipramine, Membrane Lipids, Phospholipids, Promethazine, Propranolol, Surface-Active Agents, Trimipramine.
- chemical : Anilino Naphthalenesulfonates, Diphenylhexatriene.
- chemically induced : Lipidoses, Lung Diseases.
- Binding Sites.
Abstract
Binding characteristics of nine amphiphilic drugs, which induce pulmonary phospholipidosis, to L-alpha-dipalmitoyl phosphatidylcholine (DPPC) vesicles were studied using fluorescence probes, 1,6-diphenyl-1,3,5-hexatriene and 1-anilino-8-naphthalene sulfonate (ANS) for hydrophobic and hydrophilic interactions, respectively. Drug binding to DPPC was quantitated using Scatchard analysis. The tested drugs bound to DPPC with different capacities. The order of binding capacity to hydrophobic site of DPPC using 1,6-diphenyl-1,3,5-hexatriene as fluorescence probe was promethazine greater than amiodarone greater than chlorpromazine greater than chloramphenicol greater than imipramine greater than trimipramine greater than propranolol much greater than chloroquine and chlorphentermine. Two binding affinities were evident for amiodarone, chlorpromazine, imipramine, trimipramine and promethazine. The order of binding strength at high affinity site was amiodarone greater than trimipramine greater than chlorpromazine greater than promethazine greater than imipramine. The order of drug binding capacity using ANS as fluorescence probe was chlorphentermine greater than trimipramine greater than propranolol much greater than amiodarone, chloroquine and chloramphenicol. Each of these drugs displayed a single binding affinity. Imipramine and chlorpromazine at 1 mM and higher concentrations showed intense fluorescence with ANS (5-20 microM) in the absence of DPPC indicating an interaction of these drugs with ANS. Chloroquine did not bind to either sites on DPPC. The binding of these drugs and their interactions with hydrophobic or hydrophilic sites of DPPC were correlated with their capacity to induce pulmonary phospholipidosis. These results indicate that not all the drugs which bind to DPPC in vitro induce phospholipidosis in vivo.(ABSTRACT TRUNCATED AT 250 WORDS)
PubMed: 3392651
Affiliations:
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Le document en format XML
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Coudert</name></author><author><name sortKey="Dwyer, T M" sort="Dwyer, T M" uniqKey="Dwyer T" first="T M" last="Dwyer">T M Dwyer</name></author><author><name sortKey="Mehendale, H M" sort="Mehendale, H M" uniqKey="Mehendale H" first="H M" last="Mehendale">H M Mehendale</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1988">1988</date><idno type="RBID">pubmed:3392651</idno><idno type="pmid">3392651</idno><idno type="wicri:Area/PubMed/Corpus">000571</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000571</idno><idno type="wicri:Area/PubMed/Curation">000571</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000571</idno><idno type="wicri:Area/PubMed/Checkpoint">000543</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000543</idno><idno type="wicri:Area/Ncbi/Merge">001049</idno><idno type="wicri:Area/Ncbi/Curation">001049</idno><idno type="wicri:Area/Ncbi/Checkpoint">001049</idno><idno type="wicri:doubleKey">0022-3565:1988:Joshi U:types:of:interaction</idno><idno type="wicri:Area/Main/Merge">003255</idno><idno type="wicri:Area/Main/Curation">003185</idno><idno type="wicri:Area/Main/Exploration">003185</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Types of interaction of amphiphilic drugs with phospholipid vesicles.</title><author><name sortKey="Joshi, U M" sort="Joshi, U M" uniqKey="Joshi U" first="U M" last="Joshi">U M Joshi</name><affiliation><nlm:affiliation>Department of Pharmacology and Toxicology, University of Mississippi Medical Center, Jackson.</nlm:affiliation><wicri:noCountry code="subField">Jackson</wicri:noCountry></affiliation></author><author><name sortKey="Kodavanti, P R" sort="Kodavanti, P R" uniqKey="Kodavanti P" first="P R" last="Kodavanti">P R Kodavanti</name></author><author><name sortKey="Coudert, B" sort="Coudert, B" uniqKey="Coudert B" first="B" last="Coudert">B. Coudert</name></author><author><name sortKey="Dwyer, T M" sort="Dwyer, T M" uniqKey="Dwyer T" first="T M" last="Dwyer">T M Dwyer</name></author><author><name sortKey="Mehendale, H M" sort="Mehendale, H M" uniqKey="Mehendale H" first="H M" last="Mehendale">H M Mehendale</name></author></analytic><series><title level="j">The Journal of pharmacology and experimental therapeutics</title><idno type="ISSN">0022-3565</idno><imprint><date when="1988" type="published">1988</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amiodarone (adverse effects)</term><term>Amiodarone (metabolism)</term><term>Anilino Naphthalenesulfonates</term><term>Binding Sites</term><term>Chloramphenicol (adverse effects)</term><term>Chloramphenicol (metabolism)</term><term>Chloroquine (adverse effects)</term><term>Chloroquine (metabolism)</term><term>Chlorpromazine (adverse effects)</term><term>Chlorpromazine (metabolism)</term><term>Diphenylhexatriene</term><term>Imipramine (adverse effects)</term><term>Imipramine (metabolism)</term><term>Lipidoses (chemically induced)</term><term>Lung Diseases (chemically induced)</term><term>Membrane Lipids (metabolism)</term><term>Phospholipids (metabolism)</term><term>Promethazine (adverse effects)</term><term>Promethazine (metabolism)</term><term>Propranolol (adverse effects)</term><term>Propranolol (metabolism)</term><term>Surface-Active Agents (adverse effects)</term><term>Surface-Active Agents (metabolism)</term><term>Trimipramine (adverse effects)</term><term>Trimipramine (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>1,6-Diphényl-hexa-1,3,5-triène</term><term>Amiodarone (effets indésirables)</term><term>Amiodarone (métabolisme)</term><term>Anilino-naphtalènesulfonates</term><term>Chloramphénicol (effets indésirables)</term><term>Chloramphénicol (métabolisme)</term><term>Chloroquine (effets indésirables)</term><term>Chloroquine (métabolisme)</term><term>Chlorpromazine (effets indésirables)</term><term>Chlorpromazine (métabolisme)</term><term>Imipramine (effets indésirables)</term><term>Imipramine (métabolisme)</term><term>Lipides membranaires (métabolisme)</term><term>Lipidoses ()</term><term>Maladies pulmonaires ()</term><term>Phospholipides (métabolisme)</term><term>Prométhazine (effets indésirables)</term><term>Prométhazine (métabolisme)</term><term>Propranolol (effets indésirables)</term><term>Propranolol (métabolisme)</term><term>Sites de fixation</term><term>Tensioactifs (effets indésirables)</term><term>Tensioactifs (métabolisme)</term><term>Trimipramine (effets indésirables)</term><term>Trimipramine (métabolisme)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="adverse effects" xml:lang="en"><term>Amiodarone</term><term>Chloramphenicol</term><term>Chloroquine</term><term>Chlorpromazine</term><term>Imipramine</term><term>Promethazine</term><term>Propranolol</term><term>Surface-Active Agents</term><term>Trimipramine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Amiodarone</term><term>Chloramphenicol</term><term>Chloroquine</term><term>Chlorpromazine</term><term>Imipramine</term><term>Membrane Lipids</term><term>Phospholipids</term><term>Promethazine</term><term>Propranolol</term><term>Surface-Active Agents</term><term>Trimipramine</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Anilino Naphthalenesulfonates</term><term>Diphenylhexatriene</term></keywords><keywords scheme="MESH" qualifier="chemically induced" xml:lang="en"><term>Lipidoses</term><term>Lung Diseases</term></keywords><keywords scheme="MESH" qualifier="effets indésirables" xml:lang="fr"><term>Amiodarone</term><term>Chloramphénicol</term><term>Chloroquine</term><term>Chlorpromazine</term><term>Imipramine</term><term>Prométhazine</term><term>Propranolol</term><term>Tensioactifs</term><term>Trimipramine</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Amiodarone</term><term>Chloramphénicol</term><term>Chloroquine</term><term>Chlorpromazine</term><term>Imipramine</term><term>Lipides membranaires</term><term>Phospholipides</term><term>Prométhazine</term><term>Propranolol</term><term>Tensioactifs</term><term>Trimipramine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Binding Sites</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>1,6-Diphényl-hexa-1,3,5-triène</term><term>Anilino-naphtalènesulfonates</term><term>Lipidoses</term><term>Maladies pulmonaires</term><term>Sites de fixation</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Binding characteristics of nine amphiphilic drugs, which induce pulmonary phospholipidosis, to L-alpha-dipalmitoyl phosphatidylcholine (DPPC) vesicles were studied using fluorescence probes, 1,6-diphenyl-1,3,5-hexatriene and 1-anilino-8-naphthalene sulfonate (ANS) for hydrophobic and hydrophilic interactions, respectively. Drug binding to DPPC was quantitated using Scatchard analysis. The tested drugs bound to DPPC with different capacities. The order of binding capacity to hydrophobic site of DPPC using 1,6-diphenyl-1,3,5-hexatriene as fluorescence probe was promethazine greater than amiodarone greater than chlorpromazine greater than chloramphenicol greater than imipramine greater than trimipramine greater than propranolol much greater than chloroquine and chlorphentermine. Two binding affinities were evident for amiodarone, chlorpromazine, imipramine, trimipramine and promethazine. The order of binding strength at high affinity site was amiodarone greater than trimipramine greater than chlorpromazine greater than promethazine greater than imipramine. The order of drug binding capacity using ANS as fluorescence probe was chlorphentermine greater than trimipramine greater than propranolol much greater than amiodarone, chloroquine and chloramphenicol. Each of these drugs displayed a single binding affinity. Imipramine and chlorpromazine at 1 mM and higher concentrations showed intense fluorescence with ANS (5-20 microM) in the absence of DPPC indicating an interaction of these drugs with ANS. Chloroquine did not bind to either sites on DPPC. The binding of these drugs and their interactions with hydrophobic or hydrophilic sites of DPPC were correlated with their capacity to induce pulmonary phospholipidosis. These results indicate that not all the drugs which bind to DPPC in vitro induce phospholipidosis in vivo.(ABSTRACT TRUNCATED AT 250 WORDS)</div></front></TEI><affiliations><list></list><tree><noCountry><name sortKey="Coudert, B" sort="Coudert, B" uniqKey="Coudert B" first="B" last="Coudert">B. Coudert</name><name sortKey="Dwyer, T M" sort="Dwyer, T M" uniqKey="Dwyer T" first="T M" last="Dwyer">T M Dwyer</name><name sortKey="Joshi, U M" sort="Joshi, U M" uniqKey="Joshi U" first="U M" last="Joshi">U M Joshi</name><name sortKey="Kodavanti, P R" sort="Kodavanti, P R" uniqKey="Kodavanti P" first="P R" last="Kodavanti">P R Kodavanti</name><name sortKey="Mehendale, H M" sort="Mehendale, H M" uniqKey="Mehendale H" first="H M" last="Mehendale">H M Mehendale</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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