Inverse Electron-demand Diels-Alder 반응을 이용한 핵의학 영상 프로브의 합성 및 활용

Sajid Mushtaq; 전종호; Sajid Mushtaq; Jongho Jeon

Applied Chemistry for Engineering, Vol.28, No.2, 141-152, April, 2017

DOI10.14478/ace.2017.1021 Export Citation

Inverse Electron-demand Diels-Alder 반응을 이용한 핵의학 영상 프로브의 합성 및 활용

Synthesis of PET and SPECT Radiotracers Using Inverse Electron-demand Diels-Alder Reaction

Sajid Mushtaq^{1, 2}, 전종호^{1, 2, †}

¹한국원자력연구원 첨단방사선연구소
²과학기술연합대학원대학교 방사선동위원소응용 및 생명공학과

Sajid Mushtaq^{1, 2}, and Jongho Jeon^{1, 2, †}

¹Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup, Jeonbuk 56212, Republic of Korea
²Department of Radiation Biotechnology and Applied Radioisotope Science, University of Science and Technology, Daejeon, Korea

E-mail:

초록

1,2,4,5-테트라진 유도체를 이용한 inverse electron-demand Diels-Alder (IEDDA) 반응은 다양한 생체물질, 고분자, 나노물질 복합체의 효율적인 합성에 폭넓게 활용되고 있다. IEDDA는 유기용매에서뿐만 아니라 생리학적 조건 하에서도 매우 특이적이며 빠른 반응속도를 가지고 있는 것으로 알려져 있다. 이러한 특성으로 인해 본 반응은 다양한 생물학적 활성을 가지는 물질의 방사성동위원소 표지와 분자영상 및 질병 치료를 위한 방사성의약품 개발에도 활발히 응용되고 있다. 본 리뷰 논문은 IEDDA 반응을 방사화학 및 핵의학 분야에서 이용한 최근 연구 동향 및 연구 결과 그리고 향후 전망에 대해 소개하고자 한다.

Inverse electron-demand Diels-Alder reactions (IEDDA) between tetrazine derivatives and strained dienophiles have attracted a lot of attention for the efficient conjugation of biomolecules, polymers, and nanomaterials. Excellent specificity, exceptionally fast reaction rate, and biocompatibility are key features of IEDDA. Therefore, it has also been applied to the development of new labeling methods using several radioisotopes and development of radiotracers to carry out various nuclear imaging as well as therapeutic studies. The purpose of this review is to introduce the reader to the recent advances and applications of IEDDA in the fields of radiochemistry and nuclear medicine.

Keywords:Inverse electron-demand Diels-Alder reaction;Radiolabeling;Nuclear imaging;Diagnosis;Therapy

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[2] Devaraj NK, Weissleder R, Acc. Chem. Res., 44, 816 (2011)

[3] Seckute J, Devaraj NK, Curr. Opin. Chem. Biol., 17, 761 (2013)

[4] Blackman ML, Royzen M, Fox JM, J. Am. Chem. Soc., 130(41), 13518 (2008)

[5] Schoch J, Staudt M, Samanta A, Wiessler M, Jaschke A, Bioconjugate Chem., 23, 1382 (2012)

[6] Devaraj NK, Weissleder R, Hilderbrand SA, Bioconjugate Chem., 19, 2297 (2008)

[7] Chen W, Wang D, Dai C, Hamelberg D, Wang B, Chem. Commun., 48, 1736 (2012)

[8] Patterson DM, Nazarova LA, Xie B, Kamber DN, Prescher JA, J. Am. Chem. Soc., 134(45), 18638 (2012)

[9] Engelsma SB, Willems LI, van Paaschen CE, van Kasteren SI, van der Marel GA, Overkleeft HS, Filippov DV, Org. Lett., 16, 2744 (2014)

[10] Stairs S, Neves AA, Stockmann H, Wainman YA, Ireland-Zecchini H, Brindle KM, Leeper FJ, Chembiochem, 14, 1063 (2013)

[11] Han HS, Devaraj NK, Lee J, Hilderbrand SA, Weissleder R, Bawendi MG, J. Am. Chem. Soc., 132(23), 7838 (2010)

[12] Ametamey SM, Honer M, Schubiger PA, Chem. Rev., 108(5), 1501 (2008)

[13] Hjelstuen OK, Svadberg A, Olberg DE, Rosser M, Eur. J. Pharm. Biopharm., 78, 307 (2011)

[14] Vrabel M, Kolle P, Brunner KM, Gattner MJ, Lopez-Carrillo V, de Vivie-Riedle R, Carell T, Chem.-Eur. J., 19, 13309 (2013)

[15] Li Z, Cai H, Hassink M, Blackman ML, Brown RCD, Conti PS, Fox JM, Chem. Commun., 46, 8043 (2010)

[16] Selvaraj R, Liu S, Hassink M, Huang CW, Yap LP, Park R, Fox JM, Li Z, Conti PS, Bioorg. Med. Chem. Lett., 21, 5011 (2011)

[17] Liu S, Hassink M, Selvaraj R, Yap LP, Park R, Wang H, Chen X, Fox JM, Li Z, Conti PS, Mol. Imaging, 12, 121 (2013)

[18] Reiner T, Keliher EJ, Earley S, Marinelli B, Weissleder R, Angew. Chem.-Int. Edit., 50, 1922 (2011)

[19] Wu Z, Liu S, Hassink M, Nair I, Park R, Li L, Todorov I, Fox JM, Li Z, Shively E, Conti PS, J. Nucl. Med., 54, 244 (2013)

[20] Knight JC, Richter S, Wuest M, Way JD, Wuest F, Org. Biomol. Chem., 11, 3817 (2013)

[21] Denk C, Svatunek D, Filip T, Wanek T, Lumpi D, Frohlich J, Kuntner C, Mikula H, Angew. Chem.-Int. Edit., 53, 9655 (2014)

[22] Devaraj NK, Thurber GM, Keliher EJ, Marinelli B, Weissleder R, Proc. Natl. Acad. Sci. USA, 109, 4762 (2012)

[23] Herth MM, Andersen VL, Lehel S, Madsen J, Knudsen GM, Kristensen JL, Chem. Commun., 49, 3805 (2013)

[24] Zeglis BM, Mohindra P, Weissmann GI, Divilov V, Hilderbrand SA, Weissleder R, Lewis JS, AAPG Bull., 22, 2048 (2011)

[25] Zeglis BM, Sevak KK, Reiner T, Mohindra P, Carlin SD, Zanzonico P, Weissleder R, Lewis JS, J. Nucl. Med., 54, 1389 (2013)

[26] Evans HL, Nguyen QD, Carroll LS, Kaliszczak M, Twyman FJ, Spivey AC, Aboagye EO, Chem. Commun., 50, 9557 (2014)

[27] Nichols B, Qin Z, Yang J, Vera DR, Devaraj NK, Chem. Commun., 50, 5215 (2014)

[28] Genady AR, Tan J, El-Zaria ME, Zlitni A, Janzen N, Valliant JF, J. Organomet. Chem., 798, 278 (2015)

[29] Albu SA, Al-Karmi SA, Vito A, Dzandzi JPK, Zlitni A, Beckford-Vera D, Blacker M, Janzen N, Patel RM, Capretta A, Valliant JF, Bioconjugate Chem., 27, 207 (2016)

[30] Choi MH, Shim HE, Yun SJ, Kim HR, Mushtaq S, Lee CH, Park SH, Choi DS, Lee DE, Byun EB, Jang BS, Jeon J, Bioorg. Med. Chem., 24, 2589 (2016)

[31] Rossin R, Verkerk PR, van den Bosch SM, Vulders R, Verel I, Lub J, Robillard MS, Angew. Chem.-Int. Edit., 49, 3375 (2010)

[32] Rossin R, van Duijnhoven SMJ, Lappchen T, van den Bosch SM, Robillard MS, Mol. Pharm., 11, 3090 (2014)

[33] Yazdani A, Bilton H, Vito A, Genady AR, Rathmann SM, Ahmad Z, Janzen N, Czorny S, Zeglis BM, Francesconi LC, Valliant JF, J. Med. Chem., 59, 9381 (2016)