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Investigation of Fatty Acid Ketohydrazone Modified Liposome's Properties as a Drug Carrier.

Hayashi K, Kiriishi M, Suga K, Okamoto Y, Umakoshi H - J Drug Deliv (2015)

Bottom Line: The interface of the P-KH modified liposome at acidic pH was found to become more hydrophobic and less fluidic as compared with that at neutral pH; that is, P-KH modified liposome became more rigid structure.Therefore, it seems that the P-KH modified liposome could protect encapsulated drugs from the enzymes in the lysosome.This study shows the novel approach about design of pH-responsive liposomes based on the membrane properties.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan.

ABSTRACT
pH-responsive liposomes were prepared by modifying the liposome with acid-cleaving amphiphiles. Palmitic ketohydrazone (P-KH) or stearic ketohydrazone (S-KH), composed of hydrophilic sugar headgroup and hydrophobic acyl chain, was used as a modifier of the DMPC liposome. Because the ketohydrazone group of P-KH or S-KH was cleaved at low pH conditions (

No MeSH data available.


Related in: MedlinePlus

Scheme of fatty acid ketohydrazone synthesis.
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fig1: Scheme of fatty acid ketohydrazone synthesis.

Mentions: Palmitic ketohydrazone (P-KH) and stearic ketohydrazone (S-KH) were synthesized by C-glycoside ketone and fatty acid hydrazide as shown in Figure 1 [17]. In order to synthesize C-glycoside ketone, 10 mmol of d-glucose, 10 mmol of sodium carbonate, and 12 mmol of 2,4-pentanedione were dissolved in 5 mL water. This solution was stirred for 4 hours at 90°C. Reacted solution was washed twice by ethyl acetate to remove the remaining 2,4-pentanedione from the reacted solution. After the aqueous phase was gently collected, C-glycoside ketone was lyophilized. 1.4 mmol of C-glycoside ketone and 2.1 mmol of fatty acid hydrazide were dissolved in 20 mL of methanol/ethanol (v/v = 1 : 1) and were stirred for 4 hours at 50°C. After removing the solvent by rotary evaporator, the excessive fatty acid hydrazide was removed by liquid-liquid extraction using water and 4-methyl-2-pentanone. Aqueous phase was gently collected, and the water was removed by freeze-drying completely. Obtained P-KH and S-KH were evaluated by mass spectroscopy, high pressure liquid chromatography, and FTIR to confirm the formation of hydrazone bond.


Investigation of Fatty Acid Ketohydrazone Modified Liposome's Properties as a Drug Carrier.

Hayashi K, Kiriishi M, Suga K, Okamoto Y, Umakoshi H - J Drug Deliv (2015)

Scheme of fatty acid ketohydrazone synthesis.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4663332&req=5

fig1: Scheme of fatty acid ketohydrazone synthesis.
Mentions: Palmitic ketohydrazone (P-KH) and stearic ketohydrazone (S-KH) were synthesized by C-glycoside ketone and fatty acid hydrazide as shown in Figure 1 [17]. In order to synthesize C-glycoside ketone, 10 mmol of d-glucose, 10 mmol of sodium carbonate, and 12 mmol of 2,4-pentanedione were dissolved in 5 mL water. This solution was stirred for 4 hours at 90°C. Reacted solution was washed twice by ethyl acetate to remove the remaining 2,4-pentanedione from the reacted solution. After the aqueous phase was gently collected, C-glycoside ketone was lyophilized. 1.4 mmol of C-glycoside ketone and 2.1 mmol of fatty acid hydrazide were dissolved in 20 mL of methanol/ethanol (v/v = 1 : 1) and were stirred for 4 hours at 50°C. After removing the solvent by rotary evaporator, the excessive fatty acid hydrazide was removed by liquid-liquid extraction using water and 4-methyl-2-pentanone. Aqueous phase was gently collected, and the water was removed by freeze-drying completely. Obtained P-KH and S-KH were evaluated by mass spectroscopy, high pressure liquid chromatography, and FTIR to confirm the formation of hydrazone bond.

Bottom Line: The interface of the P-KH modified liposome at acidic pH was found to become more hydrophobic and less fluidic as compared with that at neutral pH; that is, P-KH modified liposome became more rigid structure.Therefore, it seems that the P-KH modified liposome could protect encapsulated drugs from the enzymes in the lysosome.This study shows the novel approach about design of pH-responsive liposomes based on the membrane properties.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemical Engineering, National Institute of Technology, Nara College, 22 Yata-cho, Yamatokoriyama, Nara 639-1080, Japan.

ABSTRACT
pH-responsive liposomes were prepared by modifying the liposome with acid-cleaving amphiphiles. Palmitic ketohydrazone (P-KH) or stearic ketohydrazone (S-KH), composed of hydrophilic sugar headgroup and hydrophobic acyl chain, was used as a modifier of the DMPC liposome. Because the ketohydrazone group of P-KH or S-KH was cleaved at low pH conditions (

No MeSH data available.


Related in: MedlinePlus