Citation: Xuchen Huang, Yanbin Huang. Solubilization of organic compounds by arginine-derived polymers[J]. Chinese Chemical Letters, ;2015, 26(6): 636-640. doi: 10.1016/j.cclet.2015.04.009 shu

Solubilization of organic compounds by arginine-derived polymers

Xuchen Huang ,
Yanbin Huang ^,

1.
Key Laboratory of Advanced Materials (MOE), Department of Chemical Engineering, Tsinghua University, Beijing 100084, China

Corresponding author: Yanbin Huang,
Received Date: 27 January 2015
Available Online: 1 April 2015
Fund Project: This study is supported by the Natural Science Foundation of China (No. 21434008). (No. 21434008)

Poor aqueous solubility of drugs is one of the major challenges in the pharmaceutical science. In this study, a guanidinium-containing polymer based on arginine was designed and synthesized, and was evaluated as a solubility enhancing additive for three model organic compounds (coumarin, pyrene and doxorubicin). At a guanidinium group concentration of 100 mmol/L, the polymer could significantly increase the solubility of pyrene and doxorubicin by 6-and 11-fold respectively, much more effective than arginine (2-and 3-fold, respectively). In contrast, its effect on the solubility of coumarin was less effective than arginine. The solubilizing effect may be explained by the enhanced interaction between the guanidinium group in the polymer and the aromatic compounds.
- Arginine,
- Cation-π interaction,
- Drug solubilization
1. [1]
  [1] L. Di, E.H. Kerns, G.T. Carter, Drug-like property concepts in pharmaceutical design, Curr. Pharm. Des. 15 (2009) 2184-2194.
2. [2]
  [2] T. Takagi, C. Ramachandran, M. Bermejo, et al., A provisional biopharmaceutical classification of the top 200 oral drug products in the United States, Great Britain, Spain, and Japan, Mol. Pharm. 3 (2006) 631-643.
3. [3]
  [3] Y.B. Huang, W.G. Dai, Fundamental aspects of solid dispersion technology for poorly soluble drugs, Acta Pharm. Sin. B 4 (2014) 18-25.
4. [4]
  [4] Y. Zhang, M.Y. Xu, T.K. Jiang, W.Z. Huang, J.Y. Wu, Low generational polyamidoamine dendrimers to enhance the solubility of folic acid: a "dendritic effect" investigation, Chin. Chem. Lett. 25 (2014) 815-818.
5. [5]
  [5] L. Wang, L.L. Li, H.L. Ma, H. Wang, Recent advances in biocompatible supramolecular assemblies for biomolecular detection and delivery, Chin. Chem. Lett. 24 (2013) 351-358.
6. [6]
  [6] H.R. Guzman, M. Tawa, Z. Zhang, et al., Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations, J. Pharm. Sci. 96 (2007) 2686-2702.
7. [7]
  [7] K.A. Schug, W. Lindner, Noncovalent binding between guanidinium and anionic groups: focus on biological-and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues, Chem. Rev. 105 (2005) 67-114.
8. [8]
  [8] N. Sakai, S. Matile, Anion-mediated transfer of polyarginine across liquid and bilayer membranes, J. Am. Chem. Soc. 125 (2003) 14348-14356.
9. [9]
  [9] T. Arakawa, Y. Kita, A.H. Koyama, Solubility enhancement of gluten and organic compounds by arginine, Int. J. Pharm. 355 (2008) 220-223.
10. [10]
  [10] A. Hirano, T. Kameda, T. Arakawa, K. Shiraki, Arginine-assisted solubilization system for drug substances: solubility experiment and simulation, J. Phys. Chem. B 114 (2010) 13455-13462.
11. [11]
  [11] D. Shukla, B.L. Trout, Interaction of arginine with proteins and the mechanism by which it inhibits aggregation, J. Phys. Chem. B 114 (2010) 13426-13438.
12. [12]
  [12] P.E. Mason, G.W. Neilson, J.E. Enderby, et al., The structure of aqueous guanidinium chloride solutions, J. Am. Chem. Soc. 126 (2004) 11462-11470.
13. [13]
  [13] J.G. Li, M. Garg, D. Shah, R. Rajagopalan, Solubilization of aromatic and hydrophobic moieties by arginine in aqueous solutions, J. Chem. Phys. 133 (2010) 054902.
14. [14]
  [14] K. Tsumoto, M. Umetsu, I. Kumagai, et al., Role of arginine in protein refolding, solubilization, and purification, Biotechnol. Prog. 20 (2004) 1301-1308.
15. [15]
  [15] B.M. Baynes, D.I.C. Wang, B.L. Trout, Role of arginine in the stabilization of proteins against aggregation, Biochemistry 44 (2005) 4919-4925.
16. [16]
  [16] U. Das, G. Hariprasad, A.S. Ethayathulla, et al., Inhibition of protein aggregation: supramolecular assemblies of arginine hold the key, PLoS One 11 (2007) e1176.
17. [17]
  [17] J. Arakawa, M. Uegaki, T. Ishimizu, Effects of L-arginine on solubilization and purification of plant membrane proteins, Protein Expr. Purif. 80 (2011) 91-96.
18. [18]
  [18] M.M. Varughese, J. Newman, Inhibitory effects of arginine on the aggregation of bovine insulin, J. Biophys. 2012 (2012) 434289.
19. [19]
  [19] D.X. Zhao, Z.X. Huang, Effect of arginine on stability of GST-ZNF191 (243-368), Chin. Chem. Lett. 18 (2007) 355-356.
20. [20]
  [20] A. Hirano, T. Arakawa, K. Shiraki, Arginine increases the solubility of coumarin: comparison with salting-in and salting-out additives, J. Biochem. 144 (2008) 363-369.
21. [21]
  [21] J.G. Cheng, X.M. Luo, X.H. Yan, et al., Research progress in cation-p interactions, Sci. China Ser. B: Chem. 51 (2008) 709-717.
22. [22]
  [22] Y. Kim, S. Binauld, M.H. Stenzel, Zwitterionic guanidine-based oligomers mimicking cell-penetrating peptides as a nontoxic alternative to cationic polymers to enhance the cellular uptake of micelles, Biomacromolecule 13 (2012) 3418-3426.
23. [23]
  [23] Z.L. Luo, G.Z. Zhang, Scaling for sedimentation and diffusion of poly(ethylene glycol) in water, J. Phys. Chem. B 113 (2009) 12462-12465.
24. [24]
  [24] L.C. Cartwright, Vanilla-like synthetics, solubility and volatility of propenyl guaethyl, bourbonal, vanillin, and coumarin, J. Agric. Food Chem. 1 (1953) 312-314.
25. [25]
  [25] D. Mackay, W.Y. Shiu, Aqueous solubility of polynuclear aromatic hydrocarbons, J. Chem. Eng. Data 22 (1977) 399-402.
1. [1]
  Shuai Qiu , Jia He , Xiao Hu , Hongxia Yan , Zhao Gao , Wei Tian . Cation-π enhanced triplet-to-singlet Förster resonance energy transfer for fluorescence afterglow. Chinese Chemical Letters, 2025, 36(4): 110057-. doi: 10.1016/j.cclet.2024.110057
2. [2]
  Linghui Zou , Meng Cheng , Kaili Hu , Jianfang Feng , Liangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129
3. [3]
  Fengjie Liu , Fansu Meng , Zhenjiang Yang , Huan Wang , Yuehong Ren , Yu Cai , Xingwang Zhang . Exosome-biomimetic nanocarriers for oral drug delivery. Chinese Chemical Letters, 2024, 35(9): 109335-. doi: 10.1016/j.cclet.2023.109335
4. [4]
  Zhibin Ren , Shan Li , Xiaoying Liu , Guanghao Lv , Lei Chen , Jingli Wang , Xingyi Li , Jiaqing Wang . Penetrating efficiency of supramolecular hydrogel eye drops: Electrostatic interaction surpasses ligand-receptor interaction. Chinese Chemical Letters, 2024, 35(11): 109629-. doi: 10.1016/j.cclet.2024.109629
5. [5]
  Cheng Wang , Ji Wang , Dong Liu , Zhi-Ling Zhang . Advances in virus-host interaction research based on microfluidic platforms. Chinese Chemical Letters, 2024, 35(12): 110302-. doi: 10.1016/j.cclet.2024.110302
6. [6]
  Yujie Li , Ya-Nan Wang , Yin-Gen Luo , Hongcai Yang , Jinrui Ren , Xiao Li . Advances in synthetic biology-based drug delivery systems for disease treatment. Chinese Chemical Letters, 2024, 35(11): 109576-. doi: 10.1016/j.cclet.2024.109576
7. [7]
  Shaoqing Du , Xinyong Liu , Xueping Hu , Peng Zhan . Targeting novel sites represents an effective strategy for combating drug resistance. Chinese Chemical Letters, 2025, 36(1): 110378-. doi: 10.1016/j.cclet.2024.110378
8. [8]
  Qijie Gong , Jian Song , Yihui Song , Kai Tang , Panpan Yang , Xiao Wang , Min Zhao , Liang Ouyang , Li Rao , Bin Yu , Peng Zhan , Saiyang Zhang , Xiaojin Zhang . New techniques and strategies in drug discovery (2020–2024 update). Chinese Chemical Letters, 2025, 36(3): 110456-. doi: 10.1016/j.cclet.2024.110456
9. [9]
  Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
10. [10]
  Yinghui Xia , Yixi Lin , Zhenming Xu . Cation potential guiding structural regulation of lithium halide superionic conductors. Chinese Journal of Structural Chemistry, 2025, 44(3): 100448-100448. doi: 10.1016/j.cjsc.2024.100448
11. [11]
  Jinli Chen , Shouquan Feng , Tianqi Yu , Yongjin Zou , Huan Wen , Shibin Yin . Modulating Metal-Support Interaction Between Pt3Ni and Unsaturated WOx to Selectively Regulate the ORR Performance. Chinese Journal of Structural Chemistry, 2023, 42(10): 100168-100168. doi: 10.1016/j.cjsc.2023.100168
12. [12]
  Ningyue Xu , Jun Wang , Lei Liu , Changyang Gong . Injectable hydrogel-based drug delivery systems for enhancing the efficacy of radiation therapy: A review of recent advances. Chinese Chemical Letters, 2024, 35(8): 109225-. doi: 10.1016/j.cclet.2023.109225
13. [13]
  Yihan Zhou , Duo Gao , Yaying Wang , Li Liang , Qingyu Zhang , Wenwen Han , Jie Wang , Chunliu Zhu , Xinxin Zhang , Yong Gan . Worm-like micelles facilitate the intestinal mucus diffusion and drug accumulation for enhancing colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108967-. doi: 10.1016/j.cclet.2023.108967
14. [14]
  Xin Zhang , Junyu Chen , Xiang Pei , Linxin Yang , Liang Wang , Luona Chen , Guangmei Yang , Xibo Pei , Qianbing Wan , Jian Wang . Drug-loading ZIF-8 for modification of microporous bone scaffold to promote vascularized bone regeneration. Chinese Chemical Letters, 2024, 35(6): 108889-. doi: 10.1016/j.cclet.2023.108889
15. [15]
  Liping Zhao , Xixi Guo , Zhimeng Zhang , Xi Lu , Qingxuan Zeng , Tianyun Fan , Xintong Zhang , Fenbei Chen , Mengyi Xu , Min Yuan , Zhenjun Li , Jiandong Jiang , Jing Pang , Xuefu You , Yanxiang Wang , Danqing Song . Novel berberine derivatives as adjuvants in the battle against Acinetobacter baumannii: A promising strategy for combating multi-drug resistance. Chinese Chemical Letters, 2024, 35(10): 109506-. doi: 10.1016/j.cclet.2024.109506
16. [16]
  Zhilong Xie , Guohui Zhang , Ya Meng , Yefei Tong , Jian Deng , Honghui Li , Qingqing Ma , Shisong Han , Wenjun Ni . A natural nano-platform: Advances in drug delivery system with recombinant high-density lipoprotein. Chinese Chemical Letters, 2024, 35(11): 109584-. doi: 10.1016/j.cclet.2024.109584
17. [17]
  Fukui Shen , Yuqing Zhang , Guoqing Luan , Kaixue Zhang , Zhenzhen Wang , Yunhao Luo , Yuanyuan Hou , Gang Bai . Revealing drug targets with multimodal bioorthogonal AMPD probes through visual metabolic labeling. Chinese Chemical Letters, 2024, 35(12): 109646-. doi: 10.1016/j.cclet.2024.109646
18. [18]
  Cheng-Zhe Gao , Hao-Ran Jia , Tian-Yu Wang , Xiao-Yu Zhu , Xiaofeng Han , Fu-Gen Wu . A dual drug-loaded tumor vasculature-targeting liposome for tumor vasculature disruption and hypoxia-enhanced chemotherapy. Chinese Chemical Letters, 2025, 36(1): 109840-. doi: 10.1016/j.cclet.2024.109840
19. [19]
  Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
20. [20]
  Chunlei Dai , Liying Wang , Xinru You , Yi Zhao , Zhong Cao , Jun Wu . Coffee-derived self-anti-inflammatory polymer as drug nanocarrier for enhanced rheumatoid arthritis treatment. Chinese Chemical Letters, 2025, 36(3): 109869-. doi: 10.1016/j.cclet.2024.109869

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(813)
HTML views(11)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142