Citation: WAN Jing-Bai, LIU Shu-Zhen, PAN Shu-Ying, XU Xuan, LI Xu, YE Bing. Stability and Electronic Spectra of Chlorin e6 Lysine Amides[J]. Acta Physico-Chimica Sinica, ;2011, 27(01): 32-38. doi: 10.3866/PKU.WHXB20110127 shu

Stability and Electronic Spectra of Chlorin e6 Lysine Amides

WAN Jing-Bai ¹ ,
LIU Shu-Zhen ¹ ,
PAN Shu-Ying ¹ ,
XU Xuan ^1,2,3, ,
LI Xu ¹ ,
YE Bing ¹

1.
1. School of Chemistry & Environment, South China Normal University, Guangzhou, 510006, P. R. China;
2. Key Laboratory of Electrochemical Technology on Energy Storage and Power Generation in Guangdong Universities, Guangzhou 510006, P. R. China;
3. Engineering Research Center of Materials and Technology for Electrochemical Energy Storage, Ministry of Education of China, South China Normal University, Guangzhou 510006, P. R. China

Received Date: 24 July 2010
Available Online: 9 December 2010
Fund Project: 广东省教育部产学研项目(2010B090400184) (2010B090400184)广东省自然科学资金项目(9151063101000037)资助 (9151063101000037)

The geometric configurations of chlorin e6 and six designed e6 lysine amides were optimized using density functional theory at the B3LYP/6-31G^* level. Based on the obtained minimum energy structure, a single point calculation was carried out at the B3LYP/6-31G^** level. The electronic spectra of these compounds were calculated using time dependent density functional theory at the LSDA/6-31G^** level. The results indicate that the e6 lysine amides, in which the carboxyl of e6 connects with the ε-NH₂ of lysine, are more stable. Among them, the 15-acetamide Y_ε has the highest stability. The formation of lysine amides improves the water-solubility and leads to a slightly poor coplanarity of the chlorin macrocycle in e6. Therefore, the frontier orbital gaps of the e6 lysine amides are slightly higher than that of e6, causing the long wavelength absorption to a small blue-shift of 16-39 nm. The adsorption wavelength is still in the range of 600-900 nm for photodynamic therapy. Furthermore, the long wavelength absorption is strongly affected by the conformation of the molecule. By comparison with Y_ε, in which the lysine amide group and the chlorin macrocycle are almost coplanar, the planarity of the chlorin ring of Y_ε1 and Y_ε2, in which the lysine amide is almost perpendicular to the chlorin ring, is improved and results in red shifts of 53 nm and 50 nm for their long wavelength absorptions, respectively, the average adsorption wavelength of Y_ε, Y_ε1, and Y_ε2 is 18 nm larger than that of e6.
- Density functional theory,
- Chlorin e6 lysine amide,
- Electronic absorption spectrum,
- Stability
1. [1]
  
  1 Bisland, S. K.; Singh, D.; Gariépy, J. Bioconjugate Chem., 1999, 10: 982
2. [2]
  2 Uzdenskya, A. B.; Dergachevaa, O. Y.; Zhavoronkova, A. A.; Reshetnikovb, A. V.; Ponomarevc, G. V. Life Sciences, 2004, 74: 2185
3. [3]
  3 Chen, J. B.; Ou, M. R.; Li, Z. Q.; Xu, X. P. Strait Pharmaceutical Journal, 2003, 15(6): 8
4. [4]
  [陈杰波, 欧敏锐, 李忠琴, 许小平. 海峡药学, 2003, 15(6): 8]
5. [5]
  4 Spikes, J. D. J. Photochem. Photobiol. B: Biol., 1990, 6(3): 259
6. [6]
  5 Zhang, L.; Xu, D. Y. Chin. J. Org. Chem., 1999, 19(4): 424
7. [7]
  [章玲, 许德余. 有机化学, 1999, 19(4): 424]
8. [8]
  6 Pellerito, C.; D′ Agati, P.; Fiore, T.; Mansueto, C.; Mansueto, V.; Stocco, G.; Nagy, L.; Pellerito, L. J. Inorg. Biochem., 2005, 99(6): 1294
9. [9]
  7 Vermathen, M.; Vermathen, P.; Simonis, U.; Bigler, P.; Langmuir, 2008, 24(21): 12521
10. [10]
  8 Mennenga, A.; G?rtner,W.; Lubitz,W.; G?rner, H. Phys. Chem. Chem. Phys., 2006, 8: 5444
11. [11]
  9 Fang, Y.; Xu, D. Y. Chin. J. Laser Med. Surg., 1999, 8(4): 235
12. [12]
  [方瑛, 许德余. 中国激光医学杂志, 1999, 8(4): 235]
13. [13]
  10 Ol'shevskaya, V. A.; Savchenko, A. N.; Zaitsev, A. V.; Kononova, E. G.; Petrovskii, P. V.; Ramonova, A. A.; Tatarskiy, V. V.; Uvarov, O. V.; Moisenovich, M. M.; Kalinin, V. N.; Shtil, A. A. J. Organomet. Chem., 2009, 694: 1632
14. [14]
  11 Hargus, J. A.; Fronczek, F. R.; Vicente, M. G. H.; Smith, K. M. Photochem. Photobiol., 2007, 83: 1006
15. [15]
  12 Harubumi, K.; Kinya, F.; Masami, O. Lung Cancer, 2003, 42(1): 103
16. [16]
  13 Nelson, J. S.; Robert,W. G.; Berns, M.W. Cancer Res. 1987, 47: 4681
17. [17]
  14 Walsh, P. J.; rdon, K. C.; Officer, D. L. J. Mol. Struct., 2006, 759: 17
18. [18]
  15 Koseki, J.; Maezono, R.; Tachikawa, M. J. Chem. Phys., 2008, 129: 085103/1
19. [19]
  16 Kuzmitsky, V. A.; Volkovich, D. I. J. Appl. Spectrosc., 2008, 75(1): 27
20. [20]
  17 Kuz′mitskii, V. A.; Knyukshto, V. N.; Gael, V. I.; Zen′kevich, E. I.; Sagun, E. I.; Pukhlikova, N. A.; Lebedeva, V. S.; Mironov, A. F. J. Appl. Spectrosc., 2003, 70(1): 43
21. [21]
  18 Liu, X. Q.; Xu, Z. G. Comput. Appl. Chem., 2009, 26(3): 339
22. [22]
  [刘学琴, 徐志广, 计算机与应用化学, 2009, 26(3): 339]
23. [23]
  19 Pajunen, A.; Stapelbroek-M?llmann, M. E.; Hynninen, P. H. Acta Cryst., 1996, C52: 743
24. [24]
  20 Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B, 1988, 37: 785
25. [25]
  21 Reed, A. E.;Weinhold, F. J. Chem. Phys., 1983, 78: 4066
26. [26]
  22 Vosko, S. H.;Wilk, L.; Nusair, M. J. Chem. Phys., 1980, 58: 1200
27. [27]
  23 Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision B.03. Pittsburgh, PA: Gaussian Inc., 2003
28. [28]
  24 Ghose, A. K.; Pritchett, A.; Crippen, G. M. J. Comp. Chem., 1988, 9(1): 80
29. [29]
  25 Viswanadhan, V. N.; Ghose, A. K.; Revankar, G. N.; Robins, R. K. J. Chem. Inf. Comput. Sci., 1989, 29(3): 163
30. [30]
  26 Ren, X. F.; Ren, A. M.;Wang, Q.; Feng, J. K. Acta Phys. -Chim. Sin., 2010, 26(1): 110
31. [31]
  [任雪峰, 任爱民, 王钦, 封继康. 物理化学学报, 2010, 26(1): 110]
32. [32]
  27 Isakau, H. A.; Trukhacheva, T. V.; Petrov, P. T. J. Pharm. Biomed. Anal., 2007, 45: 20
33. [33]
  28 Gladkova, O. L.; Parkhats, M. V.; rbachova, A. N.; Terekhov, S. N. Spectrochimica Acta Part A, 2010, 76: 388
34. [34]
  29 Isakau, H. A.; Parkhats, M. V.; Knyukshto, V. N.; Dzhagarov, B. M.; Petrov, E. P.; Petrov, P. T. J. Photochem. Photobiol. B: Biol., 2008, 92: 165
1. [1]
  Shitao Fu , Jianming Zhang , Cancan Cao , Zhihui Wang , Chaoran Qin , Jian Zhang , Hui Xiong . Study on the Stability of Purple Cabbage Pigment. University Chemistry, 2024, 39(4): 367-372. doi: 10.3866/PKU.DXHX202401059
2. [2]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
3. [3]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
4. [4]
  Xuyang Wang , Jiapei Zhang , Lirui Zhao , Xiaowen Xu , Guizheng Zou , Bin Zhang . Theoretical Study on the Structure and Stability of Copper-Ammonia Coordination Ions. University Chemistry, 2024, 39(3): 384-389. doi: 10.3866/PKU.DXHX202309065
5. [5]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
6. [6]
  Xiaoning TANG , Junnan LIU , Xingfu YANG , Jie LEI , Qiuyang LUO , Shu XIA , An XUE . Effect of sodium alginate-sodium carboxymethylcellulose gel layer on the stability of Zn anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1452-1460. doi: 10.11862/CJIC.20240191
7. [7]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
8. [8]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
9. [9]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
10. [10]
  Mengyao Shi , Kangle Su , Qingming Lu , Bin Zhang , Xiaowen Xu . Determination of Potassium Content in Tobacco Stem Ash by Flame Atomic Absorption Spectroscopy. University Chemistry, 2024, 39(10): 255-260. doi: 10.12461/PKU.DXHX202404105
11. [11]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
12. [12]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
13. [13]
  Qin Hu , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Ni掺杂构建电子桥及激活MoS₂惰性基面增强光催化分解水产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2406024-. doi: 10.3866/PKU.WHXB202406024
14. [14]
  Meijin Li , Xirong Fu , Xue Zheng , Yuhan Liu , Bao Li . The Marvel of NAD⁺: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027
15. [15]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
16. [16]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
17. [17]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
18. [18]
  Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060
19. [19]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
20. [20]
  Yanhui XUE , Shaofei CHAO , Man XU , Qiong WU , Fufa WU , Sufyan Javed Muhammad . Construction of high energy density hexagonal hole MXene aqueous supercapacitor by vacancy defect control strategy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1640-1652. doi: 10.11862/CJIC.20240183

Get Citation

PDF

XML

Metrics

PDF Downloads(1255)
Abstract views(3062)
HTML views(47)

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