Synthesis of a dihydrotestosterone-ciprofloxacin conjugate: Relationship between descriptors logP, π, R <inf>m</inf>, and v <inf>m</inf> and its antibacterial activity in S. aureus and E. coli

Lauro Figueroa-Valverde, Francisco Díaz-Cedillo, Abelardo Camacho-Luis, Maria López Ramos, Elodia Garcia Cervera

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

In this work a dihydrotestosterone-ciprofloxacin conjugate was synthesized. The route involved preparation of a ciprofloxacin-ethylenediamine derivative by the reaction of ciprofloxacin with ethylenediamine using a carbodiimide or boric acid as catalysts. Additionally, the ciprofloxacin derivative was bound to dihydrotestosterone hemisuccinate to form the dihydrotestosterone-ciprofloxacin conjugate in the presence of a carbodiimide. The antibacterial activity of dihydrotestosterone-ciprofloxacin, as well as ciprofloxacin-ethylenediamine and ciprofloxacin, was evaluated in vitro on S. aureus and E. coli using the dilution method and the minimum inhibitory concentration. To delineate the structural chemical requirements of the compounds ciprofloxacin, ciprofloxacin-ethylenediamine and dihydrotestosterone-ciprofloxacin conjugate as antibacterial agents on S. aureus and E. coli, other parameters such as the descriptors logP, π, R m, and V m were calculated. The results showed that bacterial growth of the microorganisms studied was inhibited by ciprofloxacin, ciprofloxacin-ethylenediamine and dihydrotestosterone- ciprofloxacin in a dose-dependent manner. These data suggest that functional groups involved in the structure of the studied compounds are specific for their antibacterial activity. © 2010 Springer-Verlag.
Original languageAmerican English
Pages (from-to)373-380
Number of pages334
JournalMonatshefte fur Chemie
DOIs
StatePublished - 1 Mar 2010
Externally publishedYes

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Dihydrotestosterone
Ciprofloxacin
Escherichia coli
ethylenediamine
Carbodiimides
Derivatives
Microbial Sensitivity Tests
Microorganisms
Functional groups
Dilution

Cite this

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title = "Synthesis of a dihydrotestosterone-ciprofloxacin conjugate: Relationship between descriptors logP, π, R m, and v m and its antibacterial activity in S. aureus and E. coli",
abstract = "In this work a dihydrotestosterone-ciprofloxacin conjugate was synthesized. The route involved preparation of a ciprofloxacin-ethylenediamine derivative by the reaction of ciprofloxacin with ethylenediamine using a carbodiimide or boric acid as catalysts. Additionally, the ciprofloxacin derivative was bound to dihydrotestosterone hemisuccinate to form the dihydrotestosterone-ciprofloxacin conjugate in the presence of a carbodiimide. The antibacterial activity of dihydrotestosterone-ciprofloxacin, as well as ciprofloxacin-ethylenediamine and ciprofloxacin, was evaluated in vitro on S. aureus and E. coli using the dilution method and the minimum inhibitory concentration. To delineate the structural chemical requirements of the compounds ciprofloxacin, ciprofloxacin-ethylenediamine and dihydrotestosterone-ciprofloxacin conjugate as antibacterial agents on S. aureus and E. coli, other parameters such as the descriptors logP, π, R m, and V m were calculated. The results showed that bacterial growth of the microorganisms studied was inhibited by ciprofloxacin, ciprofloxacin-ethylenediamine and dihydrotestosterone- ciprofloxacin in a dose-dependent manner. These data suggest that functional groups involved in the structure of the studied compounds are specific for their antibacterial activity. {\circledC} 2010 Springer-Verlag.",
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Synthesis of a dihydrotestosterone-ciprofloxacin conjugate: Relationship between descriptors logP, π, R <inf>m</inf>, and v <inf>m</inf> and its antibacterial activity in S. aureus and E. coli. / Figueroa-Valverde, Lauro; Díaz-Cedillo, Francisco; Camacho-Luis, Abelardo; López Ramos, Maria; Garcia Cervera, Elodia.

In: Monatshefte fur Chemie, 01.03.2010, p. 373-380.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of a dihydrotestosterone-ciprofloxacin conjugate: Relationship between descriptors logP, π, R m, and v m and its antibacterial activity in S. aureus and E. coli

AU - Figueroa-Valverde, Lauro

AU - Díaz-Cedillo, Francisco

AU - Camacho-Luis, Abelardo

AU - López Ramos, Maria

AU - Garcia Cervera, Elodia

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Y1 - 2010/3/1

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