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]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
2. [2]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
3. [3]
  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
4. [4]
  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
5. [5]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
6. [6]
  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
7. [7]
  Mingxuan Qi , Lanyu Jin , Honghe Yao , Zipeng Xu , Teng Cheng , Qi Chen , Cheng Zhu , Yang Bai . Recent progress on electrical failure and stability of perovskite solar cells under reverse bias. Acta Physico-Chimica Sinica, 2025, 41(8): 100088-0. doi: 10.1016/j.actphy.2025.100088
8. [8]
  Wang Wang , Yucheng Liu , Shengli Chen . Use of NiFe Layered Double Hydroxide as Electrocatalyst in Oxygen Evolution Reaction: Catalytic Mechanisms, Electrode Design, and Durability. Acta Physico-Chimica Sinica, 2024, 40(2): 2303059-0. doi: 10.3866/PKU.WHXB202303059
9. [9]
  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
10. [10]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
11. [11]
  Wei Sun , Yongjing Wang , Kun Xiang , Saishuai Bai , Haitao Wang , Jing Zou , Arramel , Jizhou Jiang . CoP Decorated on Ti₃C₂T_x MXene Nanocomposites as Robust Electrocatalyst for Hydrogen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2308015-0. doi: 10.3866/PKU.WHXB202308015
12. [12]
  Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Liu Fei . 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): 2408004-0. doi: 10.3866/PKU.WHXB202408004
13. [13]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
14. [14]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
15. [15]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . Accelerated Interfacial Electron Transfer in Perovskite Solar Cell by Ammonium Hexachlorostannate Modification and fs-TAS Investigation. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-0. doi: 10.3866/PKU.WHXB202402006
16. [16]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-0. doi: 10.1016/j.actphy.2025.100064
17. [17]
  Fengying Zhang , Yanglin Mei , Yuman Jiang , Shenshen Zheng , Kaibo Zheng , Ying Zhou . Research progress of transient absorption spectroscopy in solar energy conversion and utilization. Acta Physico-Chimica Sinica, 2025, 41(9): 100118-0. doi: 10.1016/j.actphy.2025.100118
18. [18]
  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
19. [19]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
20. [20]
  Zhengkun QIN , Zicong PAN , Hui TIAN , Wanyi ZHANG , Mingxing SONG . A series of iridium(Ⅲ) complexes with fluorophenyl isoquinoline ligand and low-efficiency roll-off properties: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1235-1244. doi: 10.11862/CJIC.20240429

Get Citation

PDF

XML

Metrics

PDF Downloads(1255)
Abstract views(3178)
HTML views(59)

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