title: Synthesis and antibacterial activity of catecholate-ciprofloxacin conjugates.
abstract: The development of an efficient route to obtain artificial siderophore-antibiotic conjugates active against Gram-negative bacteria is crucial. Herein, a practical access to triscatecholate enterobactin analogues linked to the ciprofloxacin along with their antibacterial evaluation are described. Two series of conjugates were obtained with and without a piperazine linker which is known to improve the pharmacokinetics profile of a drug. A monocatecholate-ciprofloxacin conjugate was also synthesized and evaluated. The antibacterial activities against Pseudomonas aeruginosa for some conjugates are related to the iron concentration in the culture medium and seem to depend on the bacterial iron uptake systems.
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France.
authors: Sylvain
authors: S
authors: Fardeau
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France.
authors: Alexandra
authors: A
authors: Dassonville-Klimpt
authors: Pharmamens, 9 avenue Théophile Gautier, 75016 Paris, France.
authors: Nicolas
authors: N
authors: Audic
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France; Pharmamens, 9 avenue Théophile Gautier, 75016 Paris, France.
authors: André
authors: A
authors: Sasaki
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France.
authors: Marine
authors: M
authors: Pillon
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France.
authors: Emmanuel
authors: E
authors: Baudrin
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France.
authors: Catherine
authors: C
authors: Mullié
authors: Laboratoire de Glycochimie, des Antimicrobiens, et des Agroressources, CNRS FRE 3517, UFR de Pharmacie, Université de Picardie Jules Verne, F-80037 Amiens, France. Electronic address: pascal.sonnet@u-picardie.fr.
authors: Pascal
authors: P
authors: Sonnet
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002396:Catechols / Q000737:chemistry*; D002939:Ciprofloxacin / Q000737:chemistry*; D004912:Erythrocytes / Q000166:cytology / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D007502:Iron Chelating Agents / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D011550:Pseudomonas aeruginosa / Q000187:drug effects*; D017262:Siderophores / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D002396:Catechols; D007502:Iron Chelating Agents; D017262:Siderophores; D002939:Ciprofloxacin
keywords: Antibacterial; Iron chelator–ciprofloxacin conjugate; Pseudomonas; Siderophore; Trojan horse strategy