Citation: Yan Meng, Peng Wenchang, Wang Hui, Zhang Danwei, Li Zhanting. Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics[J]. Chinese Journal of Organic Chemistry, ;2019, 39(9): 2567-2573. doi: 10.6023/cjoc201903071 shu

Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics

Department of Chemistry, Fudan University, Shanghai 200438

Corresponding author: Li Zhanting, ztli@fudan.edu.cn
Received Date: 29 March 2019
Revised Date: 19 April 2019
Available Online: 26 September 2019
Fund Project: the National Natural Science Foundation of China 21890732the National Natural Science Foundation of China 21529201Project supported by the National Natural Science Foundation of China (Nos. 21432004, 21529201, 21890732)the National Natural Science Foundation of China 21432004

Figures(4)

Camptothecin derivatives exist mainly as inactive open ring carboxylates in physiological media. Tumor microenvironment is generally weakly acidic, whereas supramolecular organic frameworks can adsorb and deliver anionic antitumor drugs into tumor cells. In principle, supramolecular organic frameworks (SOFs) can adsorb and deliver camptothecin open ring carboxylates to tumor microenvironment and the delivered carboxylates can undergo lactonization to afford active molecules due to the weak acid character of the tumor microenvironment, which may lead to efficient utilization of the carboxylates as predrugs. To explore this potential, dialysis experiments for the open ring carboxylates of camptothecin, SN-38 and 10-hydroxycamptothecin in the presence of two SOFs were conducted, which revealed important adsorption and retaining capacity of the SOFs for the carboxylates. Absorption spectroscopy was also utilized to evaluate the lactonization kinetics of the three carboxylates in weakly acidic saline solution. The result reveals that at pH=6.5, the half lives of the conversion are 120, 22 and 31 h, respectively, which are considerably shorter than the time gap for repeated administrations of clinically used irinotican (14 d) or topotecan (21 d), which provides the experimental basis for further study.
- camptothecin,
- SN-38,
- 10-hydroxycamptothecin,
- open ring carboxylate,
- supramolecular organic frameworks,
- loading,
- lactonization kinetics
1. [1]
2. [2]
  (a) Martino, E.; Della Volpe, S.; Terribile, E.; Benetti, E.; Sakaj, M.; Centamore, A.; Sala, A.; Collina, S. Bioorg. Med. Chem. Lett. 2017, 27, 701.
  (b) Zunino, F.; Pratesi, G. Exp. Opin. Invest. Drugs 2004, 13, 269.
3. [3]
  Pommier, Y. Nat. Rev. Cancer 2006, 6, 789. doi: 10.1038/nrc1977
4. [4]
  (a) Underberg, W. J.; Goossen, R. M.; Smith, B. R.; Beijnen, J. H. J. Pharm. Biomed. Anal. 1990, 8, 681.
  (b) van Warmerdam, L. J.; Verweij, J.; Schellens, J. H.; Rosing, H.; Davies, B. E.; de Boer-Dennert, M.; Maes, R. A.; Beijnen, J. H. Cancer Chemother. Pharmacol. 1995, 35, 237.
  (c) Rivory, L. P. Clin. Exp. Pharmacol. Physiol. 1996, 23, 1000.
  (d) Supko, J. G.; Malspeis, L. J. Liq. Chromatogr. 1991, 14, 1779.
  (e) Gabr, A.; Kuin, A.; Aalders, M.; El-Gawly, H.; Smets, L. A. Cancer Res. 1997, 57, 4811.
5. [5]
  (a) Rowinsky, E. K.; Grochow, L. B.; Hendricks, C. B.; Ettinger, D. S.; Forastiere, A. A.; Hurowitz, L. A.; McGuire, W. P.; Sartorius, S. E.; Lubejko, B. G.; Kaufmann, S. H. J. Clin. Oncol. 1992, 10, 647.
  (b) Robert, J.; Rivory, L. Drugs Today 1998, 34, 777.
6. [6]
  (a) Thomas, C. J.; Rahier, N. J.; Hecht, S. M. Bioorg. Med. Chem. 2004, 12, 1585.
  (b) Oberlies, N. H.; Kroll, D. J. J. Nat. Prod. 2004, 67, 129.
  (c) Yuan, Y.; Dong, W.; Gao, X.; Xie, X.; Curran, D. P.; Zhang, Z. Chin. J. Chem. 2018, 36, 1035.
  (d) Driver, R. W.; Yang, L.-X. Mini-Rev. Med. Chem. 2005, 5, 425.
  (e) Curran, D. P.; Josien, H.; Bom, D.; Gabarda, A. E.; Du, W. Ann. N. Y. Acad. Sci. 2000, 922, 112.
7. [7]
  (a) Zhang, S. J. Drug Delivery Ther. 2017, 7, 76.
  (b) Palakurthi, S. Exp. Opin. Drug Delivery 2015, 12, 1911.
  (c) Botella, P.; Rivero-Buceta, E. J. Controlled Release 2017, 247, 28.
  (d) Ni, S. J. Drug Delivery Ther. 2017, 7, 73.
  (e) Bala, V.; Rao, S.; Boyd, B. J.; Prestidge, C. A. J. Controlled Release 2013, 172, 48.
  (f) Venditto, V. J.; Simanek, E. E. Mol. Pharmaceutics 2010, 7, 307.
8. [8]
  (a) Ri, M.; Suzuki, K.; Iida, S.; Hatake, K.; Chou, T.; Taniwaki, M.; Watanabe, N.; Tsukamoto, T. Intern. Med. 2018, 57, 939.
  (b) Hamaguchi, T.; Tsuji, A.; Yamaguchi, K.; Takeda, K.; Uetake, H.; Esaki, T.; Amagai, K.; Sakai, D.; Baba, H.; Kimura, M.; Matsumura, Y.; Tsukamoto, T. Cancer Chemother. Pharmacol. 2018, 82, 1021.
9. [9]
  Tran, S.; DeGiovanni, P.-J.; Piel, B.; Rai, P. Clin. Trans. Med. 2017, 6, 44. doi: 10.1186/s40169-017-0175-0
10. [10]
11. [11]
12. [12]
  (a) Tian, J.; Zhou, T.-Y.; Zhang, S.-C.; Aloni, S.; Altoe, M. V.; Xie, S.-H.; Wang, H.; Zhang, D.-W.; Zhao, X.; Liu, Y.; Li, Z.-T. Nat. Commun. 2014, 5, 5574.
  (b) Wu, Y.-P.; Yang, B.; Tian, J.; Yu, S.-B.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Chem. Commun. 2017, 53, 13367.
13. [13]
14. [14]
15. [15]
  (a) Tian, J.; Xu, Z.-Y.; Zhang, D.-W.; Wang, H.; Xie, S.-H.; Xu, D.-W.; Ren, Y.-H.; Wang, H.; Liu, Y.; Li, Z.-T. Nat. Commun. 2016, 7, 11580.
  (b) Yu, S.-B.; Qi, Q.; Yang, B.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Small 2018, 14, 1801037.
16. [16]
  (a) Liu, J.; Huang, Y.; Kumar, A. K.; Tan, A.; Jin, S.; Mozhi, A.; Liang, X.-J. Biotechnol. Adv. 2014, 32, 693.
  (b) Gillies, E. R.; Goodwin, A. P.; Fréchet, J. M. Bioconjugate Chem. 2004, 15, 1254.
  (c) Lu, Y.; Aimetti, A. A.; Langer, R.; Gu, Z. Nat. Rev. Mater. 2016, 2, 16075.
17. [17]
  (a) Zhu, J.; Jin, Z.-M. Pharm. Chem. J. 2017, 51, 491.
  (b) Chang, S.; Xie, L.; Ding H.; Nie, Y.; Wu, Y.; He, B.; Gu, Z. Pharm. Nanotechnol. 2013, 1, 115.
  (c) Zhang, J. A.; Xuan, T.; Parmar, M.; Ma, L.; Ugwu, S.; Ali, S.; Ahmad, I. Int. J. Pharm. 2004, 270, 93.
  (d) Beretta, G. L.; Zunino, F. Biochem. Pharmacol. 2007, 74, 1437.
  (e) Oguma, T. J. Chromatogr. B 2001, 764, 49.
  (f) Herben, V. M. M.; Ten, B.; Huinink, W. W.; Beijnen, J. H. Clin. Pharmacokinet. 1996, 31, 85.
18. [18]
  Yan, M.; Liu, X.-B.; Gao, Z.-Z.; Wu, Y.-P.; Hou, J-L.; Wang, H.; Zhang, D.-W.; Liu, Y.; Li, Z.-T. Org. Chem. Front. 2019, 6, 1698. doi: 10.1039/C9QO00382G
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