Quinolone antibacterial agents linked to osteotropic bisphosphonate moieties

Thomas Pieper; Bernhard Keppler

doi:10.1080/10426500108040581

Quinolone antibacterial agents linked to osteotropic bisphosphonate moieties

Thomas Pieper
, Bernhard Keppler

Department of Inorganic Chemistry

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.

Original language	English
Pages (from-to)	5-14
Number of pages	10
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	170
Issue number	1
DOIs	https://doi.org/10.1080/10426500108040581
Publication status	Published - 2001

Austrian Fields of Science 2012

1040 Chemistry

Access to Document

10.1080/10426500108040581

Cite this

@article{bf27f2a6fb8340adb7fa9c62744d2187,

title = "Quinolone antibacterial agents linked to osteotropic bisphosphonate moieties",

abstract = "Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.",

author = "Thomas Pieper and Bernhard Keppler",

note = "Zeitschrift: Phosphorus, Sulfur and Silicon and Related Elements Affiliations: Institute of Inorganic Chemistry, University of Vienna, Waehringerstr. 42, A-1090 Vienna, Austria Adressen: Keppler, B.K.; Institute of Inorganic Chemistry; University of Vienna; Waehringerstr. 42 A-1090 Vienna, Austria Source-File: ChemieErgScopus.csv Import aus Scopus: 2-s2.0-0035541915 Importdatum: 09.01.2007 14:13:07 12.02.2008: Datenanforderung 2112 (Import Sachbearbeiter) 09.02.2010: Datenanforderung UNIVIS-DATEN-DAT.RA-2 (Import Sachbearbeiter)",

year = "2001",

doi = "10.1080/10426500108040581",

language = "English",

volume = "170",

pages = "5--14",

journal = "Phosphorus, Sulfur and Silicon and the Related Elements",

issn = "1042-6507",

publisher = "TAYLOR \& FRANCIS LTD",

number = "1",

}

TY - JOUR

T1 - Quinolone antibacterial agents linked to osteotropic bisphosphonate moieties

AU - Pieper, Thomas

AU - Keppler, Bernhard

N1 - Zeitschrift: Phosphorus, Sulfur and Silicon and Related Elements Affiliations: Institute of Inorganic Chemistry, University of Vienna, Waehringerstr. 42, A-1090 Vienna, Austria Adressen: Keppler, B.K.; Institute of Inorganic Chemistry; University of Vienna; Waehringerstr. 42 A-1090 Vienna, Austria Source-File: ChemieErgScopus.csv Import aus Scopus: 2-s2.0-0035541915 Importdatum: 09.01.2007 14:13:07 12.02.2008: Datenanforderung 2112 (Import Sachbearbeiter) 09.02.2010: Datenanforderung UNIVIS-DATEN-DAT.RA-2 (Import Sachbearbeiter)

PY - 2001

Y1 - 2001

N2 - Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.

AB - Bisphosphonates are widely used in diagnosis and therapy of different bone diseases. Due to their potential to accumulate in the inorganic bone matrix hydroxylapatite they are useful agents in osteotic vectorization of different types of drugs. We linked bisphosphonate moieties to antibacterial quinolones like norfloxacin to enable a selective targeting of these agents to bone tissue. The quinolones (1,4-dihydro-4-oxo-quinoline-3-carboxylic acids) were modified at position 1 and 7 using alkylbisphosphonates with ethene-, amino- and carboxylic-groups. After coupling with the quinolones, the alkylbisphosphonic esters could smoothly be hydrolyzed via the corresponding silyl esters to obtain the free bisphosphonic acids.

U2 - 10.1080/10426500108040581

DO - 10.1080/10426500108040581

M3 - Article

SN - 1042-6507

VL - 170

SP - 5

EP - 14

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

IS - 1

ER -

Quinolone antibacterial agents linked to osteotropic bisphosphonate moieties

Abstract

Austrian Fields of Science 2012

Access to Document

Fingerprint

Cite this