A micellar prodrug of paclitaxel conjugated to cyclotriphosphazene

Yong Joo Jun; Jee Hyon Min; Da Eun Ji; Jin Hee Yoo; Ji Hyeon Kim; Hwa Jeong Lee; Byeongmoon Jeong; Youn Soo Sohn

doi:10.1016/j.bmcl.2008.10.077

A micellar prodrug of paclitaxel conjugated to cyclotriphosphazene

Yong Joo Jun, Jee Hyon Min, Da Eun Ji, Jin Hee Yoo, Ji Hyeon Kim, Hwa Jeong Lee, Byeongmoon Jeong, Youn Soo Sohn

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

15 Scopus citations

Abstract

A novel water soluble and biodegradable cyclotriphosphazene-paclitaxel conjugate was prepared by reacting 2′-succinyl paclitaxel with cyclotriphosphazenes bearing equimolar glycyl-l-lysine and methoxy poly(ethylene glycol) as side groups. The macromolecular conjugate was found to self-assemble in aqueous solution to form stable micelles with a mean hydrodynamic diameter of 24.7 nm and a low critical micelle concentration of 10 mg/L. The present conjugate exhibited lower than free paclitaxel but reasonably high in vitro cytotoxicity against selected human tumor cells due to their hydrolytic degradation in PBS solution.

Original language	English
Pages (from-to)	6410-6413
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	24
DOIs	https://doi.org/10.1016/j.bmcl.2008.10.077
State	Published - 15 Dec 2008

Keywords

Antitumor agent
Cyclotriphosphazene
Paclitaxel
Prodrug

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10.1016/j.bmcl.2008.10.077

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title = "A micellar prodrug of paclitaxel conjugated to cyclotriphosphazene",

abstract = "A novel water soluble and biodegradable cyclotriphosphazene-paclitaxel conjugate was prepared by reacting 2′-succinyl paclitaxel with cyclotriphosphazenes bearing equimolar glycyl-l-lysine and methoxy poly(ethylene glycol) as side groups. The macromolecular conjugate was found to self-assemble in aqueous solution to form stable micelles with a mean hydrodynamic diameter of 24.7 nm and a low critical micelle concentration of 10 mg/L. The present conjugate exhibited lower than free paclitaxel but reasonably high in vitro cytotoxicity against selected human tumor cells due to their hydrolytic degradation in PBS solution.",

keywords = "Antitumor agent, Cyclotriphosphazene, Paclitaxel, Prodrug",

author = "Jun, {Yong Joo} and Min, {Jee Hyon} and Ji, {Da Eun} and Yoo, {Jin Hee} and Kim, {Ji Hyeon} and Lee, {Hwa Jeong} and Byeongmoon Jeong and Sohn, {Youn Soo}",

note = "Funding Information: This work was supported by a Korea Research Foundation Grant (KRF-2004-005-C00090), by Seoul R & BD Program (10816), by the SRC program of the Korea Science and Engineering Foundation through the Center for Intelligent Nano-Bio Materials at Ewha Womans University (Grant R11-2005-008-01002-0).",

year = "2008",

month = dec,

day = "15",

doi = "10.1016/j.bmcl.2008.10.077",

language = "English",

volume = "18",

pages = "6410--6413",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd.",

number = "24",

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TY - JOUR

T1 - A micellar prodrug of paclitaxel conjugated to cyclotriphosphazene

AU - Jun, Yong Joo

AU - Min, Jee Hyon

AU - Ji, Da Eun

AU - Yoo, Jin Hee

AU - Kim, Ji Hyeon

AU - Lee, Hwa Jeong

AU - Jeong, Byeongmoon

AU - Sohn, Youn Soo

N1 - Funding Information: This work was supported by a Korea Research Foundation Grant (KRF-2004-005-C00090), by Seoul R & BD Program (10816), by the SRC program of the Korea Science and Engineering Foundation through the Center for Intelligent Nano-Bio Materials at Ewha Womans University (Grant R11-2005-008-01002-0).

PY - 2008/12/15

Y1 - 2008/12/15

N2 - A novel water soluble and biodegradable cyclotriphosphazene-paclitaxel conjugate was prepared by reacting 2′-succinyl paclitaxel with cyclotriphosphazenes bearing equimolar glycyl-l-lysine and methoxy poly(ethylene glycol) as side groups. The macromolecular conjugate was found to self-assemble in aqueous solution to form stable micelles with a mean hydrodynamic diameter of 24.7 nm and a low critical micelle concentration of 10 mg/L. The present conjugate exhibited lower than free paclitaxel but reasonably high in vitro cytotoxicity against selected human tumor cells due to their hydrolytic degradation in PBS solution.

AB - A novel water soluble and biodegradable cyclotriphosphazene-paclitaxel conjugate was prepared by reacting 2′-succinyl paclitaxel with cyclotriphosphazenes bearing equimolar glycyl-l-lysine and methoxy poly(ethylene glycol) as side groups. The macromolecular conjugate was found to self-assemble in aqueous solution to form stable micelles with a mean hydrodynamic diameter of 24.7 nm and a low critical micelle concentration of 10 mg/L. The present conjugate exhibited lower than free paclitaxel but reasonably high in vitro cytotoxicity against selected human tumor cells due to their hydrolytic degradation in PBS solution.

KW - Antitumor agent

KW - Cyclotriphosphazene

KW - Paclitaxel

KW - Prodrug

UR - http://www.scopus.com/inward/record.url?scp=56249084206&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2008.10.077

DO - 10.1016/j.bmcl.2008.10.077

M3 - Article

C2 - 18990574

AN - SCOPUS:56249084206

SN - 0960-894X

VL - 18

SP - 6410

EP - 6413

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 24

ER -

A micellar prodrug of paclitaxel conjugated to cyclotriphosphazene

Abstract

Keywords

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