물/1,2-Dichloroethane 계면에서 Cefotiam 약물 이온의 전이 반응 연구 및 약물 센서에 응용

리우샤오원; 신타제시카; 이혜진; XiaoYun Liu; Shinta Jeshycka; Hye Jin Lee

Applied Chemistry for Engineering, Vol.29, No.5, 581-588, October, 2018

DOI10.14478/ace.2018.1061 Export Citation

물/1,2-Dichloroethane 계면에서 Cefotiam 약물 이온의 전이 반응 연구 및 약물 센서에 응용

Electrochemical Study on Transfer Reaction of Ionizable Cefotiam across a Water/1,2-dichloroethane Interface and Drug Sensing Applications

리우샤오원, 신타제시카, 이혜진^†

경북대학교 자연과학대학 화학과

XiaoYun Liu, Shinta Jeshycka, and Hye Jin Lee^†

Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, 80 Daehakro, Buk-gu, Daegu-city 41566, Republic of Korea

E-mail:

초록

본 논문은 편극화된 물/1,2-dichloroethane (1,2-DCE) 계면에서 세포티암(cefotiam, CTM) 항생제 약물의 전이 반응을 전기화학적 방법으로 조사하였다. CTM 약물은 물의 pH에 따라 서로 다른 전하를 가지고 이온화되며 각 pH에서 이들 이온의 전이 반응을 연구함으로써 처음으로 CTM 약물이 좀 더 우세하게 물 또는 유기층에 분배되는 정도를 나타내는 상 분배 도표를 세웠다. 이를 바탕으로 CTM 약물의 형식 전이 전위값 및 형식 Gibbs 전이 에너지 값을 포함한 열역학적 정보와 함께 분배 계수를 포함한 중요한 약물동태학 정보를 얻었다. 특히 pH 3.0 수용액에서 양전하를 띠는 CTM 이온의 전이 반응을 순환전압전류법으로 조사한 결과 CTM 농도에 따라 측정한 전류 값이 비례하여 증가한다는 점을 확인하였다. 이를 바탕으로 CTM 이온을 정량 분석 가능한 센서를 개발하였다. 휴대성과 이동성을 보완하기 위해 polyethylene terephthalate 필름에 마이크로홀을 만들어 지지체로 사용하고, 1,2-DCE 유기용매를 polyvinylchloride-2-nitrophenyloctylether (PVC-NPOE) 유기성 젤로 대체하여 도포하는 방식으로 센서를 제작하였다. 상기 센서를 이용하여 CTM 약물을 1 μM에서 10 μM까지 정량 분석할 수 있었다.

In this article, electrochemical investigation of the transfer reaction of ionizable cefotiam (CTM), an antibiotic molecule across a polarized water/1,2-dichloroethane (water/1,2-DCE) interface was studied. Ion partition diagram providing the preferred charged form of CTM in either water or 1,2-DCE phase was established via the voltammetric evaluation of the transfer process of differently charged CTM species depending upon the pH variation of aqueous solutions. Thermodynamic information including the formal transfer potential and formal Gibbs transfer energy values in addition to important pharmacokinetics including partition coefficients of ionizable CTM were also evaluated. In particular, the current associated with the transfer of CTM present at pH 3.0 aqueous solution proportionally increased with respect to the CTM concentration which was further used for developing CTM sensitive ion sensor. In order to improve the portability and convenient usage, a single microhole interface fabricated in a supportive polyethylene terephthalate film was used of which hole was filled with a polyvinylchloride- 2-nitrophenyloctylether (PVC-NPOE) gel replacing 1,2-DCE, a toxic organic solvent. A dynamic range of 1-10 μM CTM was obtained.

Keywords:cefotiam (CTM);ITIES;formal transfer potential;partition coefficient;ionic partition diagram

[References]

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[Referenced By]

[1] Tsuchiya K, Kida M, Kondo M, Ono H, Takeuchi M, Nishi T, Antimicrob. Agents Chemother., 14, 551 (1978)

[2] Iwahi T, Tsuchiya K, Antimicrob. Agents Chemother., 18, 257 (1980)

[3] Nakao M, Nishi T, Tsuchiya K, Antimicrob. Agents Chemother., 19, 901 (1981)

[4] Watt B, Brown FV, J. Antimicrob. Chemoter., 10, 391 (1982)

[5] Fuchs PC, Barry AL, Jones RN, Thornsberry C, J. Clin. Microbiol., 22, 1045 (1985)

[6] Brogard JM, Jehl F, Willemin B, Lamalle AM, Blickle JF, Monteil H, Clin. Pharmacokinet., 17, 163 (1989)

[7] Pehourcq FDMP, Radouane A, Labat L, Bannwarth B, Pharm. Res., 12, 1535 (1995)

[8] Tawara S, Matsumoto S, Matsumoto Y, Kamimura T, Goto S, J. Antibiot., 45, 1346 (1992)

[9] Nasal A, Siluk D, Kaliszan R, Curr. Med. Chem., 10, 381 (2003)

[10] Dellis D, Giaginis C, Tsantili-Kakoulidou A, J. Pharm. Biomed. Anal., 44, 57 (2007)

[11] Fox CB, Horton RA, Harris JM, Anal. Chem., 78, 4918 (2006)

[12] Bouchard G, Carrupt PA, Testa B, Gobry V, Girault HH, Chem. Eur. J., 8, 3478 (2002)

[13] Reymond F, Chopineaux-Courtois V, Steyaert G, Bouchard G, Carrupt PA, Testa B, Girault HH, J. Electroanal. Chem., 462(2), 235 (1999)

[14] Bouchard G, Pagliara A, van Balen GP, Carrupt PA, Testa B, Gobry V, Girault HH, Caron G, Ermondi G, Fruttero R, HeIv. Chim. Acta, 84, 375 (2001)

[15] Chopineaux-Courtois V, Reymond F, Bouchard G, Carrupt PA, Testa B, Girault HH, J. Am. Chem. Soc., 121(8), 1743 (1999)

[16] Nia RP, Su B, Mendez MA, Barbe JM, Samec Z, Girault HH, J. Electroanal. Chem., 656(1-2), 147 (2011)

[17] Bouchard G, Pagliara A, Carrupt PA, Testa B, Gobry V, Girault HH, Pharm. Res., 19, 1150 (2002)

[18] Zhang M, Sun P, Chen Y, Li F, Gao Z, Shao Y, Chin. Sci. Bull., 48, 1234 (2003)

[19] Zhang M, Sun P, Chen Y, Li F, Gao Z, Shao Y, Anal. Chem., 75, 4341 (2003)

[20] Reymond F, Steyaert G, Carrupt PA, Testa B, Girault HH, Helv. Chim. Acta, 79, 101 (1996)

[21] Reymond F, Steyaert G, Carrupt PA, Morin D, Tillement JP, Girault HH, Testa B, Pharm. Res., 16, 616 (1999)

[22] Reymond F, Steyaert G, Carrupt PA, Testa B, Girault H, J. Am. Ceram. Soc., 118, 11957 (1996)

[23] Velazquez-Manzanares M, Amador-Hernandez J, Cisneros-Cisneros C, Heredia-Lezama KA, J. Electrochem. Soc., 155, 218 (2008)

[24] Hatay I, Su B, Li F, Mendez MA, Khoury T, Gros CP, Barbe JM, Ersoz M, Samec Z, Girault HH, J. Am. Chem. Soc., 131(37), 13453 (2009)

[25] Deryabina MA, Hansen SH, Jensen H, Anal. Chem., 80, 203 (2008)

[26] Samec Z, Marecek V, Koryta J, Khalil MW, J. Electroanal. Chem., 83, 393 (1977)

[27] Liu S, Li Q, Shao Y, Chem. Soc. Rev., 40, 2236 (2011)

[28] Faisal SN, Pereira CM, Rho S, Lee HJ, Phys. Chem. Chem. Phys., 12, 15184 (2010)

[29] Yoshimura Y, Hamaguchi N, Yashiki T, Int. J. Pharm., 23, 117 (1985)

[30] Rouan MC, Abadie F, Leclerc A, Juge F, J. Chromatogr., 275, 133 (1983)

[31] Elving PJ, Markowitz JM, Rosenthal I, Anal. Chem., 28, 1179 (1956)

[32] Reymond F, Carrupt PA, Testa B, Girault HH, Chem. Eur. J., 5, 39 (1999)

[33] Homolka D, Holub K, Marecek V, J. Electroanal. Chem., 138, 29 (1982)

[34] Peljo P, Girault HH, Encyclopedia of Analytical Chemistry, 1-11, John Wiley & Sons (2012).

[35] Ortuno JA, Serna C, Molina A, Gil A, Anal. Chem., 78, 8129 (2006)

[36] Stockmann TJ, Montgomery AM, Ding Z, Can. J. Chem., 90, 836 (2012)

[37] Gobry V, Ulmeanu S, Reymond F, Bouchard G, Carrupt PA, Testa B, Girault HH, J. Am. Chem. Soc., 123(43), 10684 (2001)

[38] Shao Y, Osborne MD, Girault HH, J. Electroanal. Chem., 318, 101 (1991)

[39] Liu B, Mirkin MV, Electroanalysis, 12, 1433 (2000)

[40] Strutwolf J, Scanlon MD, Arrigan DWM, J. Electroanal. Chem., 641(1-2), 7 (2010)

[41] Marecek V, Samec Z, Anal. Lett., 14, 1241 (1981)