Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.

Article Details

Citation

Luckner P, Brandsch M

Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.

Eur J Pharm Biopharm. 2005 Jan;59(1):17-24.

PubMed ID
15567297 [ View in PubMed
]
Abstract

The activity of the renal peptide transporters PEPT2 and PEPT1 determines-among other factors such as metabolic stability in liver and plasma-the circulatory half-life of penicillins and cephalosporins during therapy. This study was initiated to examine systematically the interaction of beta-lactam antibiotics with PEPT2. Interaction of 31 cephalosporins and penicillins with the carrier protein was characterized by measuring their ability to inhibit the uptake of [(14)C]Gly-Sar into renal SKPT cells. Cefadroxil, cefaclor, cyclacillin, cephradine, cephalexin and moxalactam were recognized by PEPT2 with very high affinity comparable to that of natural dipeptides (K(i)=3-100microM). Ceftibuten, dicloxacillin, amoxicillin, metampicillin, cloxacillin, ampicillin, cefixime, cefamandole, oxacillin and cefmetazole interacted with PEPT2 with medium affinity (K(i)=0.1-5mM). For the other beta-lactam antibiotics studied interaction was very low or not measurable (K(i)>5mM). The affinity constants of beta-lactam antibiotics at rPEPT2 and hPEPT1 are significantly correlated, but the rank orders are not identical. Decisive differences between PEPT1 and PEPT2 recognition of the N-terminal part of the compounds became evident. Moreover, this large data set of affinity constants of beta-lactam antibiotics will be useful for structure-transport (binding) analyses of PEPT2.

DrugBank Data that Cites this Article

Drug Targets
DrugTargetKindOrganismPharmacological ActionActions
AmpicillinSolute carrier family 15 member 1ProteinHumans
Unknown
Not AvailableDetails
BenzylpenicillinSolute carrier family 15 member 1ProteinHumans
Unknown
Substrate
Inhibitor
Details
CefotaximeSolute carrier family 15 member 1ProteinHumans
Unknown
Not AvailableDetails
CeftriaxoneSolute carrier family 15 member 1ProteinHumans
Unknown
Not AvailableDetails
OxacillinSolute carrier family 15 member 1ProteinHumans
Unknown
Not AvailableDetails
Drug Transporters
DrugTransporterKindOrganismPharmacological ActionActions
AmoxicillinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
AmoxicillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
AmpicillinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
AmpicillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
AzidocillinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
AzidocillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
BenzylpenicillinSolute carrier family 15 member 1ProteinHumans
Unknown
Substrate
Inhibitor
Details
BenzylpenicillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefaclorSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CefaclorSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefadroxilSolute carrier family 15 member 1ProteinHumans
Unknown
Substrate
Inhibitor
Details
CefadroxilSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefalotinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CefalotinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefepimeSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CefepimeSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefiximeSolute carrier family 15 member 1ProteinHumans
Unknown
Substrate
Inhibitor
Details
CefiximeSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefmetazoleSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CefmetazoleSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefotaximeSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CefotaximeSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CeftibutenSolute carrier family 15 member 1ProteinHumans
Unknown
Substrate
Inhibitor
Details
CeftibutenSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CeftriaxoneSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CeftriaxoneSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CefuroximeSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CefuroximeSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CephalexinSolute carrier family 15 member 1ProteinHumans
Unknown
Substrate
Inhibitor
Details
CephalexinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
CloxacillinSolute carrier family 15 member 1ProteinHumans
No
Inhibitor
Details
CloxacillinSolute carrier family 15 member 2ProteinHumans
No
Inhibitor
Details
CyclacillinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
CyclacillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
DicloxacillinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
DicloxacillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
OxacillinSolute carrier family 15 member 1ProteinHumans
Unknown
Inhibitor
Details
OxacillinSolute carrier family 15 member 2ProteinHumans
Unknown
Inhibitor
Details
Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
AmoxicillinSolute carrier family 15 member 1Ki (nM)>10000000N/AN/ADetails
AmpicillinSolute carrier family 15 member 1Ki (nM)14500000N/AN/ADetails
BenzylpenicillinSolute carrier family 15 member 1Ki (nM)>30000000N/AN/ADetails
CefaclorSolute carrier family 15 member 1Ki (nM)>10000000N/AN/ADetails
CefadroxilSolute carrier family 15 member 1Ki (nM)7200000N/AN/ADetails
CefalotinSolute carrier family 15 member 1Ki (nM)>10000000N/AN/ADetails
CefepimeSolute carrier family 15 member 1Ki (nM)>30000000N/AN/ADetails
CefiximeSolute carrier family 15 member 1Ki (nM)12000000N/AN/ADetails
CefmetazoleSolute carrier family 15 member 1Ki (nM)28000000N/AN/ADetails
CefotaximeSolute carrier family 15 member 1Ki (nM)>30000000N/AN/ADetails
CefradineSolute carrier family 15 member 1Ki (nM)9800N/AN/ADetails
CeftibutenSolute carrier family 15 member 1Ki (nM)340000N/AN/ADetails
CeftriaxoneSolute carrier family 15 member 1Ki (nM)>30000000N/AN/ADetails
CefuroximeSolute carrier family 15 member 1Ki (nM)>5000000N/AN/ADetails
CefuroximeSolute carrier family 15 member 1Ki (nM)26000000N/AN/ADetails
CephalexinSolute carrier family 15 member 1Ki (nM)14400000N/AN/ADetails
CloxacillinSolute carrier family 15 member 1Ki (nM)3000000N/AN/ADetails
CyclacillinSolute carrier family 15 member 1Ki (nM)500000N/AN/ADetails
DicloxacillinSolute carrier family 15 member 1Ki (nM)7200000N/AN/ADetails
OxacillinSolute carrier family 15 member 1Ki (nM)12000000N/AN/ADetails