Citation: Sun Fu-Hua, Long Yuan-Zhu, Zhou Xiao-Yong, Jiang Yi-Rou, Xie Xing-Yi. Acid dissociation constants and cytotoxicity test of a series of omega-aminoalkyl phosphates[J]. Chinese Chemical Letters, ;2016, 27(9): 1523-1530. doi: 10.1016/j.cclet.2016.03.029 shu

Acid dissociation constants and cytotoxicity test of a series of omega-aminoalkyl phosphates

Department of Polymeric Biomaterials and Artificial Organs, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China

Corresponding author: Xie Xing-Yi, xiexingyi@scu.edu.cn
Received Date: 28 January 2016
Revised Date: 11 March 2016
Accepted Date: 16 March 2016
Available Online: 24 September 2016

Figures(6)

We synthesised a series of ω-aminoalkyl sodium hydrogen phosphates (AAP-n-Na, n=3, 4, 5, 6, purity>99%), which have potential applications as bioactive cosmetic ingredients and surface modifiers of bone minerals (i.e. hydroxyapatites). Results from Fourier transformed infrared (FTIR), nuclear magnetic resonance (NMR) and high resolution mass spectroscopy, and elemental analysis all matched their chemical structures. The acid dissociation constants (pKa's) of each AAP-n (acid form of AAP-n-Na, n=2-6) were measured by potentiometric titration, showing a general increasing trend with an increase in the chain length of AAP-n. However, the pKa₃ constant, which corresponds to the deprotonation of the ammonium group in AAP-n-Na, displayed an unusual decrease when n=even. This odd-even effect can be explained by the pairwise self-association of AAP-n-Na molecules in water where intermolecular hydrogen bonding in case of n=even is weaker than that in case of n=odd. All AAP-n-Na at concentrations up to 0.1% (w/v) were non-toxic to L929 fibroblasts and MG 63 osteoblast-like cells in terms of cell growth and morphology. These basic data were important for applications of AAP-n and their salts in biomedical engineering.
- Aminoalkyl phosphates,
- Dissociation constant,
- Cytotoxicity,
- Odd-even effect,
- Hydroxyapatite
1. [1]
  Bouladjine A., Al-Kattan A., Dufour P., Drouet C.. New advances in nanocrystalline apatite colloids intended for cellular drug delivery[J]. Langmuir, 2009,25:12256-12265. doi: 10.1021/la901671j
2. [2]
  O.S. Lee, Y.H. Byon, B.S. Lee, et al., Method for preparing 3-aminopropane phosphoric acid, US 5723645, 1998.
3. [3]
  Li L.D., Tang W., Liu W.J., Zhao Z.B.. Synthesis and activity of the photoaffinitylabeled functional probe based on prenyl side-chain[J]. Chin. J. Org. Chem., 2008,28:489-493.
4. [4]
  Barker R., Olsen K.W., Shaper J.H., Hill R.L.. Agarose derivatives of uridine diphosphate and N-acetylglucosamine for the purification of a galactosyltransferase[J]. J. Biol. Chem., 1972,247:7135-7147.
5. [5]
  F.V. Emiliano, F. Giorgio, Process for preparing ethanol-2-aminophosphoric acid, US 2730542, 1956.
6. [6]
  P.V. Laakso, Method of making 2-aminoethyl phosphate, US 3644603, 1968.
7. [7]
  C. Emile, R. Joseph, Improved process for phosphorylating amino-alcohols, US 3098072, 1963.
8. [8]
  Kong W.B., Zhou X.Y., Yang Y., Xie X.Y.. A facile synthesis of ω-aminoalkyl ammonium hydrogen phosphates[J]. Chin. Chem. Lett., 2012,23:923-926. doi: 10.1016/j.cclet.2012.06.010
9. [9]
  Jiang Y.R., Sun F.H., Zhou X.Y., Kong W.B., Xie X.Y.. Water dispersible hydroxyapatite nanoparticles functionalized by a family of aminoalkyl phosphates[J]. Chin. Chem. Lett., 2015,26:1121-1128. doi: 10.1016/j.cclet.2015.04.035
10. [10]
  Maege I., Jaehne E., Henke A.. Self-assembling adhesion promoters for corrosion resistant metal polymer interfaces[J]. Prog. Org. Coat., 1998,34:1-12. doi: 10.1016/S0300-9440(98)00010-1
11. [11]
  Suflet D.M., Chitanu G.C., Popa V.I.. Phosphorylation of polysaccharides:new results on synthesis and characterisation of phosphorylated cellulose[J]. React. Funct. Polym., 2006,66:1240-1249. doi: 10.1016/j.reactfunctpolym.2006.03.006
12. [12]
  Battjes K.P., Barolo A.M., Dreyfuss P.. New evidence related to reactions of aminated silane coupling agents with carbon dioxide[J]. J. Adhes. Sci. Technol., 1991,5:785-799. doi: 10.1163/156856191X00215
13. [13]
  Fripiat J.J., Pennequin M., Poncelet G., Cloos P.. Influence of the van Der Waals force on the infrared spectra of short aliphatic alkylammonium cations held on montmorillonite[J]. Clay Miner., 1969,8:119-134. doi: 10.1180/claymin
14. [14]
  Christoffersen J., Christoffersen M.R.. Kinetics of dissolution of calcium hydroxyapatite:IV. The effect of some biologically important inhibitors[J]. J. Cryst. Growth, ,53(1981):43-54.
15. [15]
  Mohan M.S., Abbott E.H.. Metal complexes of amino acid phosphate esters[J]. Inorg. Chem., 1978,17:2203-2207. doi: 10.1021/ic50186a036
16. [16]
  Barnum D.W.. Predicting acid-base titration curves without calculations[J]. J. Chem. Educ., 1999,76:938-942. doi: 10.1021/ed076p938
17. [17]
  Hamann S.D.. The theory of titration of polybasic acids. Ⅱ. Conditions for the existence of inflexions near equivalence points[J]. Aust. J. Chem., ,23(1970):1749-1765.
18. [18]
  Sheppeck Ⅱ J.E., Kar H., Hong H.. A convenient and scaleable procedure for removing the Fmoc group in solution[J]. Tetrahedron Lett., 2000,41:5329-5333. doi: 10.1016/S0040-4039(00)00853-4
19. [19]
  D.D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London, 1965p. 967.
20. [20]
  Wang H.Q., Cheng W.N., Zhu L.Y., Hu X.G.. Enthalpic pairwise self-association of L-carnitine in aqueous solutions of some alkali halides at T=298.15 K[J]. J. Chem. Thermodyn., ,95(2016):111-115.
21. [21]
  Burrows H.D.. Studying odd-even effects and solubility behavior using α, ω-dicarboxylic acids[J]. J. Chem. Educ., 1992,69:69-73. doi: 10.1021/ed069p69
22. [22]
  Tao F., Bernasek S.L.. Understanding odd-even effects in organic self-assembled monolayers[J]. Chem. Rev., 2007,107:1408-1453. doi: 10.1021/cr050258d
1. [1]
  Jin Wang , Xiaoyan Pan , Junyu Zhang , Qingqing Zhang , Yanchen Li , Weiwei Guo , Jie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187
2. [2]
  Chuan Li , Yangyang Han , Yanan Zhai , Ke Li , Xingzhong Liu , Zhuan Zhang , Cai Jia , Yongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019
3. [3]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
4. [4]
  Jing JIN , Zhuming GUO , Zhiyin XIAO , Xiujuan JIANG , Yi HE , Xiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)₃I₃]^- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458
5. [5]
  Yue Pan , Wenping Si , Yahao Li , Haotian Tan , Ji Liang , Feng Hou . Promoting exciton dissociation by metal ion modification in polymeric carbon nitride for photocatalysis. Chinese Chemical Letters, 2024, 35(12): 109877-. doi: 10.1016/j.cclet.2024.109877
6. [6]
  Fanxin Kong , Hongzhi Wang , Huimei Duan . Inhibition effect of sulfation on Pt/TiO2 catalysts in methane combustion. Chinese Journal of Structural Chemistry, 2024, 43(5): 100287-100287. doi: 10.1016/j.cjsc.2024.100287
7. [7]
  Min Fu , Pan He , Sen Zhou , Wenqiang Liu , Bo Ma , Shiying Shang , Yaohao Li , Ruihan Wang , Zhongping Tan . An unexpected stereochemical effect of thio-substituted Asp in native chemical ligation. Chinese Chemical Letters, 2024, 35(8): 109434-. doi: 10.1016/j.cclet.2023.109434
8. [8]
  Yixia Zhang , Caili Xue , Yunpeng Zhang , Qi Zhang , Kai Zhang , Yulin Liu , Zhaohui Shan , Wu Qiu , Gang Chen , Na Li , Hulin Zhang , Jiang Zhao , Da-Peng Yang . Cocktail effect of ionic patch driven by triboelectric nanogenerator for diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109196-. doi: 10.1016/j.cclet.2023.109196
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]
  Botao Gao , He Qi , Hui Liu , Jun Chen . Role of polarization evolution in the hysteresis effect of Pb-based antiferroelecrtics. Chinese Chemical Letters, 2024, 35(4): 108598-. doi: 10.1016/j.cclet.2023.108598
11. [11]
  Xin Huang , Yi Zhao , Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278
12. [12]
  Cunjun Li , Wencong Liu , Xianlei Chen , Liang Li , Shenyu Lan , Mingshan Zhu . Adsorption and activation of peroxymonosulfate on BiOCl for carbamazepine degradation: The role of piezoelectric effect. Chinese Chemical Letters, 2024, 35(10): 109652-. doi: 10.1016/j.cclet.2024.109652
13. [13]
  Ziyou Zhang , Te Ji , Hongliang Dong , Zhiqiang Chen , Zhi Su . Effect of coordination restriction on pressure-induced fluorescence evolution. Chinese Chemical Letters, 2024, 35(12): 109542-. doi: 10.1016/j.cclet.2024.109542
14. [14]
  Shaohua Zhang , Xiaojuan Dai , Wei Hao , Liyao Liu , Yingqiao Ma , Ye Zou , Jia Zhu , Chong-an Di . A first-principles study of the Nernst effect in doped polymer. Chinese Chemical Letters, 2024, 35(12): 109837-. doi: 10.1016/j.cclet.2024.109837
15. [15]
  Xingxing Jiang , Yuxin Zhao , Yan Kong , Jianju Sun , Shangzhao Feng , Xin Lu , Qi Hu , Hengpan Yang , Chuanxin He . Support effect and confinement effect of porous carbon loaded tin dioxide nanoparticles in high-performance CO₂ electroreduction towards formate. Chinese Chemical Letters, 2025, 36(1): 109555-. doi: 10.1016/j.cclet.2024.109555
16. [16]
  Mingxin Song , Lijing Xie , Fangyuan Su , Zonglin Yi , Quangui Guo , Cheng-Meng Chen . New insights into the effect of hard carbons microstructure on the diffusion of sodium ions into closed pores. Chinese Chemical Letters, 2024, 35(6): 109266-. doi: 10.1016/j.cclet.2023.109266
17. [17]
  Chaochao Wei , Ru Wang , Zhongkai Wu , Qiyue Luo , Ziling Jiang , Liang Ming , Jie Yang , Liping Wang , Chuang Yu . Revealing the size effect of FeS₂ on solid-state battery performances at different operating temperatures. Chinese Chemical Letters, 2024, 35(6): 108717-. doi: 10.1016/j.cclet.2023.108717
18. [18]
  Chenlu Huang , Xinyu Yang , Qingyu Yu , Linhua Zhang , Dunwan Zhu . Gas-generating polymersomes-based amplified photoimmunotherapy for abscopal effect and tumor metastasis inhibition. Chinese Chemical Letters, 2024, 35(6): 109680-. doi: 10.1016/j.cclet.2024.109680
19. [19]
  Junchen Peng , Xue Yin , Dandan Dong , Zhongyuan Guo , Qinqin Wang , Minmin Liu , Fei He , Bin Dai , Chaofeng Huang . Promotion effect of epoxy group neighboring single-atom Cu site on acetylene hydrochlorination. Chinese Chemical Letters, 2024, 35(6): 109508-. doi: 10.1016/j.cclet.2024.109508
20. [20]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(576)
HTML views(17)

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