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Antibacterial Derivatives of Ciprofloxacin to Inhibit Growth of Necrotizing Fasciitis Associated Penicillin Resistant Escherichia coli.

Bartzatt R, Cirillo SL, Cirillo JD - J Pharm (Cairo) (2013)

Bottom Line: These values of Log P and polar surface area improved tissue penetration, as indicated by the determination of dermal permeability coefficient (K p ) and subsequently into the superficial fascial layer.All drugs induced greater than 60% bacterial cell death at concentrations less than 1.0 micrograms/milliliter.The ester derivatives of ciprofloxacin showed strong antibacterial activity toward penicillin resistant E. coli.

View Article: PubMed Central - PubMed

Affiliation: University of Nebraska, College of Arts & Sciences, Durham Science Center, Department of Chemistry, Omaha, NE 68182, USA.

ABSTRACT
Escherichia coli (E. coli) is associated with necrotizing fasciitis (type I) and can induce enough damage to tissue causing hypoxia. Three ester derivatives of the broad-spectrum antibiotic ciprofloxacin were placed into bacteria culture simultaneously with the parent ciprofloxacin (drug 1) to ascertain the level of antibacterial activity. The n-propyl (drug 2), n-pentyl (drug 3), and n-octyl (drug 4) esters of ciprofloxacin were synthesized under mixed phase conditions and by microwave excitation. The formation of ester derivatives of ciprofloxacin modified important molecular properties such as Log P and polar surface area which improves tissue penetration, yet preserved strong antibacterial activity. The Log P values for drugs 1, 2, 3, and 4 became -0.701, 0.437, 1.50, and 3.02, respectively. The polar surface areas for drugs 1, 2, 3, and 4 were determined to be 74.6 Angstroms(2), 63.6 Angstroms(2), 63.6 Angstroms(2), and 63.6 Angstroms(2), respectively. These values of Log P and polar surface area improved tissue penetration, as indicated by the determination of dermal permeability coefficient (K p ) and subsequently into the superficial fascial layer. All drugs induced greater than 60% bacterial cell death at concentrations less than 1.0 micrograms/milliliter. The ester derivatives of ciprofloxacin showed strong antibacterial activity toward penicillin resistant E. coli.

No MeSH data available.


Related in: MedlinePlus

Comparative molecular structures of ciprofloxacin and ester derivatives. Drug 2 is the n-propyl derivative followed by drug 3 (n-pentyl derivative) and drug 4 (n-octyl derivative). The formation of an ester group (–C(O)OR) to replace the original carboxyl group (–C(O)OH) and the type of ester moiety imparts substantial changes in molecular properties. The alteration in molecular properties involves descriptors such as Log P, polar surface area, molecular weight, and molecular volume. Beneficial changes will enhance drug likeness of the medicament.
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Related In: Results  -  Collection


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fig1: Comparative molecular structures of ciprofloxacin and ester derivatives. Drug 2 is the n-propyl derivative followed by drug 3 (n-pentyl derivative) and drug 4 (n-octyl derivative). The formation of an ester group (–C(O)OR) to replace the original carboxyl group (–C(O)OH) and the type of ester moiety imparts substantial changes in molecular properties. The alteration in molecular properties involves descriptors such as Log P, polar surface area, molecular weight, and molecular volume. Beneficial changes will enhance drug likeness of the medicament.

Mentions: Ciprofloxacin is clearly a versatile and potent antibacterial agent that was utilized in this study along with three aliphatic ester derivatives of ciprofloxacin. The molecular structures of parent ciprofloxacin (drug 1), n-propyl ester (drug 2), n-pentyl ester (drug 3), and n-octyl ester (drug 4) are presented in Figure 1 for comparison. Note that the original carboxyl group (–C(O)OH) of the parent ciprofloxacin is replaced by ester functional groups (–C(O)OR) in subsequent derivatives drug 2, drug 3, and drug 4. All other structural features of ciprofloxacin are preserved in derivatives.


Antibacterial Derivatives of Ciprofloxacin to Inhibit Growth of Necrotizing Fasciitis Associated Penicillin Resistant Escherichia coli.

Bartzatt R, Cirillo SL, Cirillo JD - J Pharm (Cairo) (2013)

Comparative molecular structures of ciprofloxacin and ester derivatives. Drug 2 is the n-propyl derivative followed by drug 3 (n-pentyl derivative) and drug 4 (n-octyl derivative). The formation of an ester group (–C(O)OR) to replace the original carboxyl group (–C(O)OH) and the type of ester moiety imparts substantial changes in molecular properties. The alteration in molecular properties involves descriptors such as Log P, polar surface area, molecular weight, and molecular volume. Beneficial changes will enhance drug likeness of the medicament.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4590791&req=5

fig1: Comparative molecular structures of ciprofloxacin and ester derivatives. Drug 2 is the n-propyl derivative followed by drug 3 (n-pentyl derivative) and drug 4 (n-octyl derivative). The formation of an ester group (–C(O)OR) to replace the original carboxyl group (–C(O)OH) and the type of ester moiety imparts substantial changes in molecular properties. The alteration in molecular properties involves descriptors such as Log P, polar surface area, molecular weight, and molecular volume. Beneficial changes will enhance drug likeness of the medicament.
Mentions: Ciprofloxacin is clearly a versatile and potent antibacterial agent that was utilized in this study along with three aliphatic ester derivatives of ciprofloxacin. The molecular structures of parent ciprofloxacin (drug 1), n-propyl ester (drug 2), n-pentyl ester (drug 3), and n-octyl ester (drug 4) are presented in Figure 1 for comparison. Note that the original carboxyl group (–C(O)OH) of the parent ciprofloxacin is replaced by ester functional groups (–C(O)OR) in subsequent derivatives drug 2, drug 3, and drug 4. All other structural features of ciprofloxacin are preserved in derivatives.

Bottom Line: These values of Log P and polar surface area improved tissue penetration, as indicated by the determination of dermal permeability coefficient (K p ) and subsequently into the superficial fascial layer.All drugs induced greater than 60% bacterial cell death at concentrations less than 1.0 micrograms/milliliter.The ester derivatives of ciprofloxacin showed strong antibacterial activity toward penicillin resistant E. coli.

View Article: PubMed Central - PubMed

Affiliation: University of Nebraska, College of Arts & Sciences, Durham Science Center, Department of Chemistry, Omaha, NE 68182, USA.

ABSTRACT
Escherichia coli (E. coli) is associated with necrotizing fasciitis (type I) and can induce enough damage to tissue causing hypoxia. Three ester derivatives of the broad-spectrum antibiotic ciprofloxacin were placed into bacteria culture simultaneously with the parent ciprofloxacin (drug 1) to ascertain the level of antibacterial activity. The n-propyl (drug 2), n-pentyl (drug 3), and n-octyl (drug 4) esters of ciprofloxacin were synthesized under mixed phase conditions and by microwave excitation. The formation of ester derivatives of ciprofloxacin modified important molecular properties such as Log P and polar surface area which improves tissue penetration, yet preserved strong antibacterial activity. The Log P values for drugs 1, 2, 3, and 4 became -0.701, 0.437, 1.50, and 3.02, respectively. The polar surface areas for drugs 1, 2, 3, and 4 were determined to be 74.6 Angstroms(2), 63.6 Angstroms(2), 63.6 Angstroms(2), and 63.6 Angstroms(2), respectively. These values of Log P and polar surface area improved tissue penetration, as indicated by the determination of dermal permeability coefficient (K p ) and subsequently into the superficial fascial layer. All drugs induced greater than 60% bacterial cell death at concentrations less than 1.0 micrograms/milliliter. The ester derivatives of ciprofloxacin showed strong antibacterial activity toward penicillin resistant E. coli.

No MeSH data available.


Related in: MedlinePlus