Citation: Dai Lingzi, Guo Nian, Liu Yaqin, Shen Shanshan, Ge Qiufu, Pan Yuanjiang. Analysis of the binding sites with NL-101 to amino acids and peptides by HPLC/MS/MS[J]. Chinese Chemical Letters, ;2019, 30(1): 103-106. doi: 10.1016/j.cclet.2017.12.023 shu

Analysis of the binding sites with NL-101 to amino acids and peptides by HPLC/MS/MS

a.
Department of Chemistry, Zhejiang University, Hangzhou 310027, China
b.
Hangzhou Pharmaceutical Group Co., Ltd., Hangzhou 311100, China

Corresponding author: Pan Yuanjiang, panyuanjiang@zju.edu.cn
Received Date: 17 November 2017
Revised Date: 25 December 2017
Accepted Date: 27 December 2017
Available Online: 30 January 2017

Figures(4)

The binding between NL-101, a novel nitrogen mustard anti-cancer drug, with amino acids and peptides has been investigated by high performance liquid chromatography electrospray tandem mass spectrometry (HPLC/ESI-MS/MS). This study offers supporting data of the interaction among drug and amino acids and peptides, which could potentially explain the cytotoxic and mutagenic effects of the drug. Collision-induced dissociation (CID) experiment demonstrated that under the same collision energy, the amino group combined with NL-101 adducts are sensitive and often produce more fragment ions; the carboxyl group combined with NL-101 adducts are hard to break and display fewer fragment ions. In addition, when other group (like sulfhydryl group) of amino acids binds to NL-101, CID spectra show different fragmentation pattern. These differences could display structural information about the drug adducts and be utilized as location of the authentic binding sites.
- High-performance liquid chromatography/,
- tandem mass spectrometry,
- NL-101,
- Amino acids,
- Peptides,
- Binding sites
1. [1]
  R. Bansal, P.C. Acharya, Chem. Rev. 114(2014) 6986-7005. doi: 10.1021/cr4002935
2. [2]
  S. Balcome, S. Park, D.Q. Dorr, et al., Chem. Res. Toxicol. 17(2004) 950-962. doi: 10.1021/tx0499463
3. [3]
  S.M. Rink, P.B. Hopkins, Biochemistry 34(1995) 1439-1445. doi: 10.1021/bi00004a039
4. [4]
  J.T. Millard, R.J. Spencer, P.B. Hopkins, Biochemistry 37(1998) 5211-5219. doi: 10.1021/bi972862r
5. [5]
  R.F. Struck, R.L. Davis, M.D. Berardini, et al., Cancer Chemoth. Pharm. 45(2000) 59-62. doi: 10.1007/PL00006744
6. [6]
  R. Jirásko, M. Holcapek, Mass. Spectrom. Rev. 30(2011) 10139-1036.
7. [7]
  C. Iacobucci, S. Reale, F.D. Angelis, Angew. Chem. Int. Ed. 55(2016) 2980-2993. doi: 10.1002/anie.201507088
8. [8]
  R.J. O'Hair, N.J. Rijs, Acc. Chem. Res. 48(2015) 329-340. doi: 10.1021/ar500377u
9. [9]
  D. Schröder, Acc. Chem. Res. 45(2012) 1521-1532. doi: 10.1021/ar3000426
10. [10]
  L.J. Kinlen, Am. J. Med. 78(1985) 44-49.
11. [11]
  S. Balcome, S. Park, D.Q. Dorr, et al., Chem. Res. Toxicol. 17(2004) 950-962. doi: 10.1021/tx0499463
12. [12]
  R. Loeber, E. Michaelson, Q.M. Fang, et al., Chem. Res. Toxicol. 21(2008) 787-795. doi: 10.1021/tx7004508
13. [13]
  D. Noort, A.G. Hulst, R. Jansen, Arch. Toxicol. 76(2002) 83-88. doi: 10.1007/s00204-001-0318-2
14. [14]
  A. Groehler, P.W. Villalta, C. Campbell, et al., Chem. Res. Toxicol. 29(2016) 190-202. doi: 10.1021/acs.chemrestox.5b00430
15. [15]
  C.S. Sevier, C.A. Kaiser, Nat. Rev. 3(2002) 836-847.
16. [16]
  M. Ruoppolo, F. Vinci, T.A. Klink, et al., Biochemistry 39(2000) 12033-12042. doi: 10.1021/bi001044n
17. [17]
  J.A. Zapp, D.W. Wilson, J. Biol. Chem. 126(1938) 19-27.
18. [18]
  O.I. Aruoma, M.J. Laughton, B. Halliwell, Biochem. J. 264(1989) 863-869. doi: 10.1042/bj2640863
19. [19]
  G.I. Klebanov, Y. Teselkin, I.V. Babenkova, et al., Membr. Cell Biol. 12(1998) 89-99.
20. [20]
  L. Pilgeram, Cardiovasc. Eng. 10(2010) 78-83. doi: 10.1007/s10558-010-9092-1
21. [21]
  L. Pickart, J. Biomater, Sci. Polymer Ed. 19(2008) 969-988.
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沈阳化工大学材料科学与工程学院沈阳 110142