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Pubmed ID :25337819
Publication Date : //

Amino acid-linked porphyrin-nitroimidazole antibiotics targeting Porphyromonas gingivalis.


The periodontal pathogen Porphyromonas gingivalis requires porphyrin supplementation for growth. Previously, in order to inhibit P. gingivalis growth, we synthesised very effective 'Trojan horse' ester and amide-linked deuterporphyrin-nitroimidazole (DPIX-Nim) adducts that exploited this requirement to transport metronidazole-derived antibiotics with excellent antimicrobial selectivity and recognition by the HA2 porphyrin binding site. Herein, in the context of developing topical agents to target P. gingivalis, l-amino acids are incorporated into adducts as linkers to improve uptake. Ten 13- and 17-propionic amide regioisomers of l-amino acid-linked deuterporphyrin-nitroimidazole adducts were synthesised using a peptide coupling approach. DPIX-Lys regioisomers without attached nitroimidazole were also synthesised as comparison compounds. All the porphyrin adducts bound (Kd50 7 to 20 nM) to a recombinant HA2 receptor with similar binding affinity to haem, except the lysine-proline linked DPIX-Lys(Boc)Pro-Nim adducts (Kd50 300 nM) and the DPIX-Lys(Nim)-Nim adducts (Kd50 200 nM), both of which have large appended groups. DPIX-Lys(Boc)-Nim, DPIX-Lys(OH)-Nim, and DPIX-Pro-Nim adducts were shown to be very effective against P. gingivalis. DPIX-Lys(Boc)Pro-Nim adducts and DPIX-Lys(Nim)-Nim adducts showed weak activity. Importantly, DPIX-Lys(Boc)-Nim adducts were selective for P. gingivalis and, unlike metronidazole, did not kill a range of other anaerobic bacteria isolated from the human gastrointestinal tract.

Authors : Dingsdag Simon A , Yap Benjamin C-M , Hunter Neil , Crossley Maxwell J ,

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EIAAB36968 Amino acid transporter A1,MNat2,Mouse,Mus musculus,Nat2,N-system amino acid transporter 2,Slc38a1,Snat1,Sodium-coupled neutral amino acid transporter 1,Solute carrier family 38 member 1,System A amino
EIAAB46684 Homo sapiens,Human,Monocyte amino acid permease 2,MOP-2,SLC7A7,Solute carrier family 7 member 7,y(+)L-type amino acid transporter 1,Y+L amino acid transporter 1,Y+LAT1,y+LAT-1
EIAAB36973 Amino acid transporter A2,ATA2,Homo sapiens,Human,KIAA1382,Protein 40-9-1,SAT2,SLC38A2,SNAT2,Sodium-coupled neutral amino acid transporter 2,Solute carrier family 38 member 2,System A amino acid trans
EIAAB46686 Cationic amino acid transporter, y+ system,Homo sapiens,Human,KIAA0245,SLC7A6,Solute carrier family 7 member 6,y(+)L-type amino acid transporter 2,Y+L amino acid transporter 2,Y+LAT2,y+LAT-2
EIAAB36958 Lyaat1,LYAAT-1,Lysosomal amino acid transporter 1,Neutral amino acid_proton symporter,Pat1,Proton_amino acid transporter 1,Proton-coupled amino acid transporter 1,Rat,Rattus norvegicus,Slc36a1,Solute
EIAAB37135 Amino acid transporter ATB0+,Colonic system B0+ amino acid transporter CATB0+,Mouse,Mus musculus,Slc6a14,Sodium- and chloride-dependent neutral and basic amino acid transporter B(0+),Solute carrier fa
EIAAB36967 Amino acid transporter A1,Ata1,Glnt,Glutamine transporter,N-system amino acid transporter 2,Rat,rATA1,Rattus norvegicus,Sa2,Sat1,Slc38a1,Snat1,Sodium-coupled neutral amino acid transporter 1,Solute ca
EIAAB36970 Amino acid transporter A2,Ata2,Kiaa1382,Mouse,Mus musculus,Sat2,Slc38a2,Snat2,Sodium-coupled neutral amino acid transporter 2,Solute carrier family 38 member 2,System A amino acid transporter 2,System
EIAAB36974 Amino acid transporter A2,Ata2,Rat,Rattus norvegicus,Sa1,Sat2,Slc38a2,Snat2,Sodium-coupled neutral amino acid transporter 2,Solute carrier family 38 member 2,System A amino acid transporter 2,System A
EIAAB36969 Amino acid transporter A1,ATA1,Homo sapiens,Human,NAT2,N-system amino acid transporter 2,SAT1,SLC38A1,SNAT1,Sodium-coupled neutral amino acid transporter 1,Solute carrier family 38 member 1,System A a
EIAAB36972 Amino acid transporter A2,Bos taurus,Bovine,Protein 40-9-1,SLC38A2,SNAT2,Sodium-coupled neutral amino acid transporter 2,Solute carrier family 38 member 2,System A amino acid transporter 2,System A tr
orb90067 Human D-Amino Acid Oxidase protein DAAO Human Recombinant fused with 20 amino acid His tag at N-terminus produced in E.coli is a single, non-glycosylated, polypeptide chain containing 367 amino acids 2
EIAAB36978 Amino acid transporter A3,ATA3,Homo sapiens,Human,Na(+)-coupled neutral amino acid transporter 4,NAT3,SLC38A4,SNAT4,Sodium-coupled neutral amino acid transporter 4,Solute carrier family 38 member 4,Sy
EIAAB36986 Homo sapiens,Human,Na(+)-coupled neutral amino acid transporter 6,NAT1,NAT-1,N-system amino acid transporter 1,Probable sodium-coupled neutral amino acid transporter 6,SLC38A6,SNAT6,Solute carrier fam
EIAAB36971 Amino acid transporter A2,Chicken,Gallus gallus,RCJMB04_2k20,SLC38A2,SNAT2,Sodium-coupled neutral amino acid transporter 2,Solute carrier family 38 member 2,System A amino acid transporter 2,System A
EIAAB36976 mNAT,Mouse,Mus musculus,Na(+)-coupled neutral amino acid transporter 3,N-system amino acid transporter 1,Slc38a3,Sn1,Snat3,Sodium-coupled neutral amino acid transporter 3,Solute carrier family 38 memb
EIAAB36980 Amino acid transporter A3,Ata3,Mouse,Mus musculus,Na(+)-coupled neutral amino acid transporter 4,Nat3,Slc38a4,Snat4,Sodium-coupled neutral amino acid transporter 4,Solute carrier family 38 member 4,Sy


 

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