중합성 Bolaamphiphile 분자의 합성과 특성에 관한 연구

진지영; 고석범; 정명희; 최경희; 이연식

Journal of the Korean Industrial and Engineering Chemistry, Vol.8, No.1, 59-66, February, 1997

Export Citation

중합성 Bolaamphiphile 분자의 합성과 특성에 관한 연구

A Study on the Synthesis and Characterization of Polymerizable Bolaamphiphiles

진지영, 고석범, 정명희, 최경희, 이연식

초록

Di(10-hemisuccinyloxy)decyl muconate(DDM)와 di(6-hemisuccinyloxy)hexyl muconate(DHM)가 합성되었으며, 수용액에 분산되어 각각 97℃과 79℃에서 상전이를 나타내었다. 이들은 자체적으로, 또는 콜레스테롤이나 dioleoylphosphatidylethanolamine (DOPE)을 혼합하여도 리포좀을 형성하지 않았지만, phosphatidylcholine(PC)과 혼합되면 리포좀을 형성하였다. 리포좀막에서 DHM이 254nm의 자외선에 노출될 때 1,2-중합반응이 쉽게 진행되었다. DOPE/dioleoylphosphatidylcholine(DOPC)/DHM(3/3/1)으로 구성된 리포좀은 중성 pH에서는 안정하지만 약산성 pH에서는 불안정하여 pH 4.8과 5.8의 phosphate-buffered saline(PBS, 37℃)에서 30분과 50분 이내에 각각 봉입된 calcein의 방출이 완료되었다. calcein의 방출은 pH가 감소됨에 따라서 증가하며 pH 5.5와 5.0 근처에서는 각각 봉입 calcein의 50%와 100%가 방출되었다.

Di(10-hemisuccinyloxy)decyl muconate(DDM) and di(6-hemisuccinyloxy)hexyl muconate(DHM) were synthesized, and showed a phase transition in an aqueous solution at 97 and 79℃, respectively. They did not form liposomes by themselves or even in the presence of cholesterol or dioleoylphosphatidylethanolamine(DOPE), but did form liposomes when they were mixed with phosphatidylcholine(PC). DHM molecules in liposome membranes were readily polymerized via 1,2-polymerization process on exposure to 254nm. Liposomes composed of DOPE/dioleoylphosphatidylcholine(DOPC)/DHM(3/3/1) were stable at neutral pH, but leaky at weakly acidic pH. The leakage of entrapped calcein from liposomes in phosphate-buffered saline (PBS, 37℃) of pH 4.8 and 5.8 was complete within 30 and 50 min, respectively. The release of toke entrapped calcein was increased with decreasing pH such that 50% and 100% of the calcein were released at pH near 5.5 and 5.0, respectively.

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[2] Ringsdorf H, Schlarb B, Venzmer J, Angew. Chem.-Int. Edit., 27, 113 (1988)

[3] Lee YS, Yang JZ, Sisson TM, Frankel DA, Gleeson JT, Aksay E, Keller SL, Gruner SM, Obrien DF, J. Am. Chem. Soc., 117(20), 5573 (1995)

[4] Lamparski H, Liman V, Frankel D, Barry JA, Ramaswami V, Brown MF, O'Brien DF, Biochemistry, 31, 685 (1992)

[5] Gregordiadis G, Tibtech December, 13, 527 (1995)

[6] Allen TM, Chonn A, Febs Lett., 223, 42 (1987)

[7] Klibano AL, Myuyama K, Torchilin VP, Huang L, Febs Lett., 268, 235 (1990)

[8] Blume G, Cevc G, Biochim. Biophys. Acta, 1029, 91 (1990)

[9] Yatvin MB, Weinstein JN, Dennis WH, Blumethal R, Science, 202, 1290 (1978)

[10] Yatvin M, Kreutz W, Horwitz B, Shinitzky M, Science, 210, 1253 (1980)

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[12] Duzgunes N, Straubinger RM, Baldwin PA, Friends DS, Papahadjopoulos D, Biochemistry, 32, 1069 (1985)

[13] Yamauchi K, Moriya A, Kinoshita M, Biochim. Biophys. Acta, 1003, 151 (1989)

[14] Kushwaha SC, Kates M, Sprott GD, Smith ICP, Science, 211, 1163 (1981)

[15] Fuhrhop JH, David HH, Mathieu J, Liman U, Winter HJ, Boekema E, J. Am. Chem. Soc., 108, 1785 (1986)

[16] Hebert N, Beck A, Lennox RB, Just G, J. Org. Chem., 57, 177 (1992)

[17] Yamauchi K, Yamamoto I, Kinoshita M, J. Chem. Soc.-Chem. Commun., 445 (1988)

[18] Bader H, Ringsdorf H, Faraday Discuss. Chem. Soc., 81, 329 (1986)

[19] Fuhrhop JH, Fritsch D, Accounts Chem. Res., 19, 130 (1986)

[20] Bader H, Ringsdorf H, J. Polym. Sci. A: Polym. Chem., 20, 1623 (1982)

[21] Okahata Y, Kunitake T, J. Am. Chem. Soc., 101, 5231 (1979)

[22] Mass RA, Fujita T, Okumura Y, Langmuir, 7, 2415 (1991)

[23] Jeong MH, Lee YS, Jin JY, Ko SB, Bull. Korean Chem. Soc., 17, 875 (1996)

[24] Pick U, Arch. Biochem. Biophys., 212, 186 (1981)

[25] Menger FM, Chen XY, Brocchini S, Hopkins HP, Hamilton D, J. Am. Chem. Soc., 115, 6600 (1993)

[26] Lamparski H, Lee YS, Sells TD, O'Brien DF, J. Am. Chem. Soc., 115, 8096 (1993)

[27] Silvius JR, Gagne J, Biochemistry, 23, 3232 (1984)

[28] Marsh D, "Handbook of Liquids Bilayer," CRC Press, Inc. (1990)

[29] Ho RJY, Rouse B, Huang L, Biochemistry, 25, 5500 (1986)

[30] Laschewsky A, Ringsdorf H, Schmidt G, Thin Solid Films, 134, 153 (1985)

[31] Collins D, Lintzinger DC, Huang L, Biochim. Biophys. Acta, 1025, 234 (1990)

[32] Tari AM, Fuller N, Boni LT, Collines D, Rand P, Huang L, Biochim. Biophys. Acta, 1192, 253 (1994)