Synthesis and physicochemical properties of new tripodal amphiphiles bearing fatty acids as a hydrophobic group

Prakash G. Avaji; Vithal B. Jadhav; Jin Xin Cui; Yong Joo Jun; Hwa Jeong Lee; Youn Soo Sohn

doi:10.1016/j.bmcl.2013.01.052

Synthesis and physicochemical properties of new tripodal amphiphiles bearing fatty acids as a hydrophobic group

Prakash G. Avaji, Vithal B. Jadhav, Jin Xin Cui, Yong Joo Jun, Hwa Jeong Lee, Youn Soo Sohn

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Saturated fatty acids (FA) were grafted using tyrosine as a spacer group to the cyclotriphosphazene ring along with equimolar hydrophilic methoxy poly(ethylene glycol) (MPEG) in cis-nongeminal way. Seven new cyclotriphosphazene amphiphiles were prepared from combinations of hydrophilic MPEGs with different molecular weights of 350, 550, 750 and 1000 and four different fatty acids of different hydrophobicity including lauric, myristic, palmitic and stearic acids. These steric amphiphiles bearing fatty acids as a hydrophobic group were found to form more stable micelles with very low critical micelle concentrations (CMC) (2.95-7.80 mg/L) compared with oligopeptide analogues, and their highly hydrophobic core environment is unique and potentially useful for various biomedical applications.

Original language	English
Pages (from-to)	1763-1767
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2013.01.052
State	Published - 15 Mar 2013

Bibliographical note

Funding Information:
This study was supported by a Grant of the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea ( A110562 ), by National Research Foundation of Korea (NRF) Grant funded by the Korean Government (MEST) ( 2012-0005453 ), and by the RP-Grant 2012 and Ewha Global Top 5 Grant 2012 of Ewha Womans University.

Keywords

Cyclotriphosphazene
Drug delivery
Fatty acid
Micelle
Tripodal amphiphile

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10.1016/j.bmcl.2013.01.052

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abstract = "Saturated fatty acids (FA) were grafted using tyrosine as a spacer group to the cyclotriphosphazene ring along with equimolar hydrophilic methoxy poly(ethylene glycol) (MPEG) in cis-nongeminal way. Seven new cyclotriphosphazene amphiphiles were prepared from combinations of hydrophilic MPEGs with different molecular weights of 350, 550, 750 and 1000 and four different fatty acids of different hydrophobicity including lauric, myristic, palmitic and stearic acids. These steric amphiphiles bearing fatty acids as a hydrophobic group were found to form more stable micelles with very low critical micelle concentrations (CMC) (2.95-7.80 mg/L) compared with oligopeptide analogues, and their highly hydrophobic core environment is unique and potentially useful for various biomedical applications.",

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author = "Avaji, {Prakash G.} and Jadhav, {Vithal B.} and Cui, {Jin Xin} and Jun, {Yong Joo} and Lee, {Hwa Jeong} and Sohn, {Youn Soo}",

note = "Funding Information: This study was supported by a Grant of the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea ( A110562 ), by National Research Foundation of Korea (NRF) Grant funded by the Korean Government (MEST) ( 2012-0005453 ), and by the RP-Grant 2012 and Ewha Global Top 5 Grant 2012 of Ewha Womans University. ",

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doi = "10.1016/j.bmcl.2013.01.052",

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AU - Jadhav, Vithal B.

AU - Cui, Jin Xin

AU - Jun, Yong Joo

AU - Lee, Hwa Jeong

AU - Sohn, Youn Soo

N1 - Funding Information: This study was supported by a Grant of the Korea Health Technology R&D Project, Ministry of Health & Welfare, Republic of Korea ( A110562 ), by National Research Foundation of Korea (NRF) Grant funded by the Korean Government (MEST) ( 2012-0005453 ), and by the RP-Grant 2012 and Ewha Global Top 5 Grant 2012 of Ewha Womans University.

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N2 - Saturated fatty acids (FA) were grafted using tyrosine as a spacer group to the cyclotriphosphazene ring along with equimolar hydrophilic methoxy poly(ethylene glycol) (MPEG) in cis-nongeminal way. Seven new cyclotriphosphazene amphiphiles were prepared from combinations of hydrophilic MPEGs with different molecular weights of 350, 550, 750 and 1000 and four different fatty acids of different hydrophobicity including lauric, myristic, palmitic and stearic acids. These steric amphiphiles bearing fatty acids as a hydrophobic group were found to form more stable micelles with very low critical micelle concentrations (CMC) (2.95-7.80 mg/L) compared with oligopeptide analogues, and their highly hydrophobic core environment is unique and potentially useful for various biomedical applications.

AB - Saturated fatty acids (FA) were grafted using tyrosine as a spacer group to the cyclotriphosphazene ring along with equimolar hydrophilic methoxy poly(ethylene glycol) (MPEG) in cis-nongeminal way. Seven new cyclotriphosphazene amphiphiles were prepared from combinations of hydrophilic MPEGs with different molecular weights of 350, 550, 750 and 1000 and four different fatty acids of different hydrophobicity including lauric, myristic, palmitic and stearic acids. These steric amphiphiles bearing fatty acids as a hydrophobic group were found to form more stable micelles with very low critical micelle concentrations (CMC) (2.95-7.80 mg/L) compared with oligopeptide analogues, and their highly hydrophobic core environment is unique and potentially useful for various biomedical applications.

KW - Cyclotriphosphazene

KW - Drug delivery

KW - Fatty acid

KW - Micelle

KW - Tripodal amphiphile

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ER -

Synthesis and physicochemical properties of new tripodal amphiphiles bearing fatty acids as a hydrophobic group

Abstract

Bibliographical note

Keywords

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