中文
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (10): 1952-1963 Previous Articles   Next Articles

• Review •

Structures and Functions of Metalloporphyrin Protein Conjugates

Wang   Rongmin**   Zhu Yongfeng   He Yufeng   Li Yan   Mao Chongwu   He Naipu   

  1. (Key Laboratory of Eco-Environment-Related Polymer Materials of Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, Institute of Polymer, Northwest Normal University, Lanzhou 730070, China)
  • Received: Revised: Online: Published:
  • Contact: Wang Rongmin E-mail:wangrmcn@163.com
PDF ( 3394 ) Cited
Export

EndNote

Ris

BibTeX

Proteins and metalloporphyrins are typical biopolymer and metal complexes. Their conjugates, biopolymer metal complexes are very important in vital movement. In this paper, based on introducing structure and major types of proteins and metalloporphyrins, metalloporphyrin-protein conjugates and their functions were reviewed. Firstly, natural metalloporphyrin-protein conjugates were summarized. Such as Cytochrome P450, Hemoglobin, Myoglobin, peroxidase and neuroglobin. They are ubiquitous in organism and play an important role in the process of biological metabolism. Their structure and functions have been characterized. Secondly, artificial conjugates of metalloporphyrin-protein were reviewed. For example, protoporphyrin IX metal complexes and some meso-substituted porphyrin metal complexes had been bound into proteins. Thirdly, recombinant protein, which is prepared by using gene recombination technology, had bound with synthetic metalloporphyrins. The structure and function of recombinant protein are same with natural protein. They also have some advantages, such as large-scale producing and avoiding the pollution. The typical conjugates, such as hemoglobin-based polymer and vesicles, recombinant human serum albumin (rHSA) binding pocket ferrous porphyrin, and protoporphyrin IX Zn(II) complexes / rHSA conjugates, were prepared and applied in blood substitutes ( oxygen carrier), medicine ( drugs treatment of cancer), or photoinduced reduction of water for preparing hydrogen.

Contents
1 The structure and types of protein and metalloporphyrins
2 Natural conjugates of metalloporphyrins and protein - hemoprotein
2.1 Cytochrome-P450
2.2 Peroxidase
2.3 NO synthase
2.4 Hemoglobin
2.5 Hemoglobin-based oxygen carriers
2.6 Myoglobin
2.7 Neuroglobin
3 Artificial conjugates of porphyrin and protein
3.1 Natural porphyrin binding with albumin
3.2 Synthetic porphyrin binding with albumin
4 Synthetic porphyrin binding with biosynthetic protein
4.1 Artificial synthetic protein - recombinant protein
4.2 Albumin binding pocket ferricporphyrin - artificial blood
4.3 Metalloporphyrins protein conjugates as drugs.

[1 ] 王荣民(Wang R M) . 第4 章细胞色素P450 的结构与功能
( Chapter 4 Structure and Functions of Cytochrome P450 ) . 《酶
化学》( Enzyme Chemistry) ,李树本主编( Ed. Li S B) . 北
京: 化学工业出版社( Beijing: Chemical Industry Press ) ,
2008. 41—68
[2 ] Winslow R M. Blood Substitutes. London: Academic Press,
2006
[3 ] Komatsu T,Wang R M,Zunszain P A,Tsuchida E. J. Am.
Chem. Soc. ,2006,128(50) : 16297—16301
[4 ] Branden C,Tooze J. Introduction to protein structure(2nd ed) .
New York: Garland Publishing,1999. 84—86
[5 ] Lu Y,Berry S M,Pfister T D. Chem. Rev. ,2001,101(10) :
3047—3080
[6 ] Regan L,DeGrado W F. Science,1988,241: 976—978
[7 ] Hecht M H,Richardson J S,Richardson D C,Ogden R C.
Science,1990,249(4971) : 884—891
[8 ] Handel T,DeGrado W F. J. Am. Chem. Soc. ,1990,112:
6710—6711
[9 ] Sligar S G,Egeberg K D,Sage J T,Morikis D,Champion P M.
J. Am. Chem. Soc. ,1987,109: 7896—7897
[10] 王荣民(Wang R M) ,赵明( Zhao M) ,何玉凤(He Y F) ,郝
二霞(Hao E X) ,申国瑞( Shen G R) . 化学进展( Progress in
Chem. ) ,2007,19(11) : 1783—1790
[11] Ciardelli E, Tsuchida E, Wohrle D. Macromolecule-Metal
Complexes. Berlin: Springer,1996. 130—150
[12] Kadish K K,Smith K M,Guilard R. The Porphyrin Handbook.
New York: Academic Press,2000. Vol 1—10
[13] 李臻( Li Z) ,夏春谷( Xia C G) . 化学进展( Prog. Chem. ) ,
2002,14(5) : 384—390
[14] Fujii H. Coord. Chem. Rev. ,2002,226: 51—60
[15] He Y F,Wang R M,Wang Y P,Xia C G. Eur. Polym. J. ,
2002,38: 2129—2132
[16] Al-Kassim L,Wang Z,Szabo A G,Taylor K E,Mutus B. J.
Chem. Techn. Biotechn. ,2005,80(9) : 1026—1030
[17] Baldo M A,O′ Brien D F,You Y,Shoustikov A,Sibley S,
Thompson M E,Forrest S R. Nature,1998,395: 151—154
[18] Shi W M,Zhang G,Dai G F,Zhang Y X,Zhao J,Tao J C.
Bioorg. Med. Chem. ,2008,16: 5665—5671
[19] Wang H M,Jiang J Q,Xiao J H,Gao R L,Lin F Y,Liu X Y.
Chemico- Biological Interactions,2008,172(2) : 154———158
[20] Robertson C A,Evans D H,Abrahamse H. J. Photochem.
Photobio. B-Bio,2009,96(1) : 1—8
[21] Florian M,Vincent S,Cyril R,Robert G,Sandra A,Caroline
L,Yves Q,Noboru O,Pierre K. Bioorg. Med. Chem. ,2009,
17(22) : 7647—7657
[22] Sieroń A, Kwiatek S. Photodiagnosis and Photodynamic
Therapy,2009,6(2) : 73—78
[23] Daltrop O,Ferguson S J. J. Biol. Chem. ,2004,279 ( 44 ) :
45347—45353
[24] Heme,Wikipedia,(2009-11-23 ) . [2010-01-13 ]. http: / / en.
wikipedia. org /wiki /Heme
[25] Rinco O,Brenton J,Douglas A,Maxwell A,Henderson M,
Indrelie K,Wessels J,Widin J. Photochem. Photobio. A:
Chem. ,2009,208(2 /3) : 91—96
[26] Turano P,Lu Y. Handbook on Metalloproteins ( Eds: Bertini I,
Sigel H,Sigel A) . New York: Marcel Dekker,2001. 269—356
[27] Moore G R, Pettigrew G W. Cytochrome C: Evolutionary,
Structural and Physiological Aspects. Berlin: Springer-Verlag,
1990
[28] Denisov I G,Makris T M,Sligar S G,Schlichting I. Chem.
Rev. ,2005,105(6) : 2253—2277
[29] Poulos T L,Finzel B C,Gunsalus I C,Wagner G C,Kraut J.
J. Biol. Chem. ,1985,260: 16122—16130
[30] Catalase,Wikipedia,( 2010-01-15 ) . [2010-01-17 ]. http: / /
en. wikipedia. org /wiki /Catalase
[31] Casella L,Poli S, Gullotti M, Selvaggini C, Beringhelli T,
Marchesini A. Biochemistry,1994,33: 6377—6386
[32] Koide N,Sugiyama T,Mu M M,Mori I,Yoshida T,Hamano
T,Yokochi T. Microbiol. Immunol. ,2003,43(9) : 669—679
[33] Loibl S,Von-Minckwitz G,Weber S,Sinn H P,Schini-Kerth V
B,Lobysheva I,Nepveu F,Wolf G,Strebhardt K,Kaufmann
M. J. Cancer Res. Clin. Oncol. ,2002,95(6) : 1191—1198
[34] Taguchi M,Alfer J,Chwalisz K,Beier H M,Classen-Linke I.
Mol. Hum. Reprod. ,2000,6(2) : 185—190
[35] Tan D Y,Cheng S B,Chen X L,Zhang S M,Yang H Z,Peng
X,Tang C S,Zhang C,Meng X Z. Acta Physiologica Sinica,
200l,53(2) : 117— 122
[36] Horinaka S,Kobayashi N,Mori Y,Yaqi H,Onoda M,Matsuoka
H. Cardiology,2003,91(1) : 25—35
[37] Chang T M. Trends in Biotechnology,2006,24(8) : 372—377
[38] Paoli M,Liddington R,Tame J,Wilkinson A,Dodson G. J.
Mol. Biol. ,1996,256(4) : 775—792
[39] Squires J E. Science,2002,295(5557) : 1002—1005
[40] Hoffman S J,Looker D L,Roehrich J M,Cozart P E,Durfee S
L,Tedesco J L,Stetler G L. Proc. Natl. Acad. Sci. U S A,
1990. 87(21) : 8521—8525
[41] Kobayashi K, Tsuchida E, Horinouchi H. Artificial Oxygen
Carrier. Tokyo: Springer,2005
[42] Chatterjee R,Welty E V,Walder R Y,Pruitt S L,Rogers P H,
Arnone A,Walder J A. J. Biol. Chem. ,1986,261 ( 21 ) :
9929—9937
[43] Sakai H,Sou K,Horinouchi H,Kobayashi K,Tsuchida E.
Artificial Organs,2009,33(2) : 139—145
[44] Sakai H,Sou K,Horinouchi H,Kobayashi K. Tsuchida E. J.
Intern. Med. ,2008,263: 4—15
[45] Takano T. Molecular Biology,1977,110(3) : 537—568
[46] Wittenberg B A,Wittenberg J B. Ann. Rev. Physiol. ,1989,
51: 857—878
[47] Pablo T,Yolanda F,Víctor M. Biomacromolecules,2004,5
(6) : 2201—2211
[48] Roesner A,Fuchs C,Hankeln T,Burmester T. Mol. Biol.
Evol. ,2005,22(1) : 12—20
[49] Burmester T,Weich B, Reinhardt S, Hankeln T. Nature,
2000,407 (6803) : 520—523
[50] Pesce A,Dewilde S,Nardini M,Moens L,Ascenzi P,Hankeln
T,Burmester T,Bolognesi M. Micron,2004,35 ( 1 /2 ) : 63—
65
[51] Vandergon T L,Riggs C K,Gorr T A,Colacino J M,Riggs A
F. Biolog. Chem. ,1998,273(27) : 16998—17011
[52] Ankita V,Priyankar S,Ejaz A,Mohd R,Naidu S,Hasan K R.
Chirality,2010,22(1) : 77—87
[53] Peters T. All About Albumin: Biochemistry, Genetics, and
Medical Applications. San-Diego: Academic Press,1996
[54] BSA,Wikipedia,( 2010-01-15 ) . [2010-01-17 ]. http: / / en.
wikipedia. org /wiki /Bovine_serum_albumin
[55] Guo J X,Xu S K,Li X Z,Tong J,Jiang Y C,Xin C Y. Acta
Laser Biol. Sinica,2006,15(2) : 171—174
[56] Kalasinsky K S,Kalasinsky V F. Spectrochim. Acta Part AMol.
,Biomol. Spectr. ,2005,61(7) : 1707—1713
[57] Masilamania V,Al-Zhrania K,Al-Salhia M,Al-Diabb A,Al-
Ageilyc M. J. Lumin. ,2004,109: 143—154
[58] Tian J N,Liu X H,Zhao Y C,Zhao S L. Luminescence,2007,
22(5) : 446—454
[59] Zhou B,Zhang Z,Zhang Y,Li R,Xiao Q,Liu Y,Li Z.
Pharmaceutical Sci. ,2009,98(1) : 105—113
[60] Wardell M,Wang Z,Ho J X,Robert J,Ruker F,Ruble J,
Carter D C. Biochem. Biophys. Res. Commun. ,2002,291:
813—819
[61] Chow J M,Huang G C,Lin H Y,Shen S C,Yang L Y,Chen Y
C. Toxicology Letters,2008,177(2) : 97—107
[62] Komatsu T,Ohmichi N,Nakagawa A,Zunszain P A,Curry S,
Tsuchida E. J. Am. Chem. Soc. ,2005,127 ( 45 ) : 15933—
15942
[63] 刘全宏( Liu Q H) ,孙世惠( Sun S H) ,肖娅萍( Xiao Y P) ,
齐浩(Qi H) ,尚志远( Shang Z Y) ,张军平( Zhang J P) ,张
金选( Zhang J X) ,任耀辉(Ren Y H) ,李萌( Li M) ,李青( Li
Q) . 中国科学( C 辑) ( Sci. China ( C) ) ,2002,32 ( 5 ) :
454—462
[64] Nishide N,Miyoshi N. Life Sci. ,2002,72(3) : 321—328
[65] Wang X F,Wang J,Zhang Z H,Xiong D Z,Chen L J,Xu R,
Zhang X D. Acta Chim. Sinica,2008,66(3) : 355—361
[66] Zhang W B,Zhang L H,Ping G C,Zhang Y K,Kettrup A. J.
Chromat. B: Anal. Techn. Biomed. Life Sci. ,2002,768(1) :
211—214
[67] Ding Y S,Lin B,Huie C W. Electrophoresis,2001,22 (11 ) :
2210—2216
[68] Sadzuka Y,Iwasaki F,Sugiyama I,Horiuchi K,Hirano T,
Ozawa H,Kanayama N,Sonobe T. Pharmaceutics,2007,338
(1 /2) : 306—309
[69] Danton M,Lim C K. Biomedical Chromatography,2007,21
(5) : 534—545
[70] Sil S,Bose T,Roy D,Chakraborti A S. Biosci. ,2004,29
(3) : 281—291
[71] Lottner C,Bart K C,Bernhardt G,Brunner H. J. Medicinal
Chem. ,2002,45(10) : 2064—2078
[72] Kubát P,Lang K,Anzenbacher P J. Biochim. Biophys. Acta,
2004,1670(1) : 40—48
[73] Valanciunaite J, Bagdonas S, Streckyte G, Rotomskis R.
Photochem. Photobiol. Sci. ,2006,5(4) : 381—388
[74] Andrade S M,Costa S M B. Biophy. J. , 2002, 82 ( 3 ) :
1607—1609
[75] Tian F,Johnson E M,Zamarripa M,Sansone S,Brancaleon L.
Biomacromolecules,2007,8(12) : 3767—3778
[76] Zhang H F,Pan J H,Chang H B,Liu Y,Guo Y J,Lu F. Acta
Pharmaceutica Sinica,2006,41(3) : 203—209
[77] 陈莹( Chen Y) ,姚闽娜(Yao M N) ,唐尧基( Tang Y J) ,李
耀群( Li Y Q) . 光谱学与光谱分析( Spectroscopy and Spectral
Analysis) ,2005,25(12) : 2048—2051
[78] Chudinov A V,Rumyantseva V D,Lobanov A V,Chudinova G
K,Stomakhin A A,Mironov A F. Russ. J. Bioorg. Chem. ,
2004,30(1) : 89—93
[79] Vzorov A N,Dixon D W,Trommel J S,Marzilli L G,Compans
R W. Antimicrobial Agents and Chemotherapy,2002,46(12) :
3917—3925.
[80] 李早英( Li Z Y) ,张悦宁( Zhang Y N) ,谢征( Xie Z) ,朱训
进( Zhu X J) ,高震霆( Gao Z T) ,刘义( Liu Y) . 化学学报
(Acta Chimica Sinica) ,2002,60(5) : 917—925
[81] Song R,Kim Y S,Lee C O,Sohn Y S. Tetrahedron Lett. ,
2003,44(8) : 1537—1540
[82] Borissevitch I E,Tominaga T T,Imasato H,Tabak M. Anal.
Chim. Acta,1997,343(3) : 281—286
[83] Andrade S M,Costa S M B. Chem. Eur. J. ,2006,12 ( 4 ) :
1046—1057
[84] Liu P,Liu Y,Li X,Huang W G. Chin. J. Chem. ,2007,25
(7) : 917—920
[85] 贾涛( Jia T) ,王凯(Wang K) ,鲍小平( Bao X P) ,赵一玫
( Zhao Y M) ,李早英( Li Z Y) . 高等学校化学学报( Chem.
J. Chin. Univ. ) ,2004,25(9) : 1604— 1607
[86] Yin Y B,Wang Y N,Ma J B. Spectrochim. Acta Part A-Mol.
Biomol. Spectr. ,2006,64: 1032—1038
[87] Chatterjee S,Srivastava T S. J. Porphyrins Phthalocyanines,
2000,4(2) : 147—157
[88] Li G R,Wu J J, Jin W J. Spectrochim. Acta Part A-Mol.
Biomol. Spectr. ,2004,60: 265— 269
[89] Bordbar A K, Eslami A, Tangestaninejad S. J. Porphyrins
Phthalocyanines,2002,6: 225—232
[90] Karapetyan N H,Madakyan V N. Russian J. Bioorg. Chem. ,
2004,30(2) : 172—177
[91] 郭灿城(Guo C C) ,李和平( Li H P) ,张晓兵( Zhang X B) ,
童荣标( Tong R B) . 高等学校化学学报( Chem. J. Chin.
Univ. ) ,2003,24(2) : 282—287
[92] 李春涯( Li C Y) ,侯安新(Hou A X) ,鲍伟( Bao W) ,王长发
(Wang C F) . 中国稀土学报( J. Chin. Rare Earth Soc. ) ,
2004,22(2) : 266—270
[93] Sumi A,Okuyama K,Kobayashi K,Ohtani W,Ohmura T,
Yokoyama K. Bioseparation,1999,8(1 /5) : 195—200
[94] Ohtani W,Ohda T,Sumi A,Kobayashi K,Ohmura O. Anal.
Chem. ,1998,70: 425—429
[95] Sugio S,Kashima A,Mochizuki S,Noda M,Kobayashi K.
Protein Engineering, Design and Selection, 1999, 12 ( 6 ) :
439—446
[96] Ohtani W,Nawa Y,Takeshima K,Kamuro H,Kobayashi K,
Ohmura T. Anal. BioChem. ,1999,256(1) : 56—62
[97] Bosse D,Praus M,Kiessling P,Nyman L,Andresen C,Waters
J,Schindel F. J. Clin. Pharm. ,2005,45(1) : 57—67
[98] Collman J P,Boulatov R,Sunderland C J,Fu L. Chem. Rev. ,
2004,104: 561—588
[99] Komatsu T,Matsukawa Y,Tsuchida E. Bioconjugate Chem. ,
2000,11: 772—776
[100] Komatsu T,Matsukawa Y,Tsuchida E. Bioconjugate Chem. ,
2001,12(1) : 71—75
[101] Tsuchida E,Komatsu T,Matsukawa Y,Hamamatsu K,Wu J.
Bioconjugate Chem. ,1999,10(5) : 797—802
[102] Komatsu T, Oguro Y, Nakagawa A, Tsuchida E.
Biomacromolecules,2005,6(6) : 3397—3403
[103]Wang R M,Komatsu T,Nakagawa A,Tsuchida E. Bioconjugate
Chem. ,2005,16: 23—26
[104] Huang Y B, Komatsua T, Yamamoto H, Horinouchic H,
Kobayashi K,Tsuchida E. Biomaterials,2006,27:4477—4483
[105] Komatsu T,Ishihara S,Tsuchida E,Nishide H,Morokuma C,
Nakamura S. Biomacromolecules,2005,6: 1489—1494
[106] Kobayashi K,Komatsu T,Iwamaru A. Biomed. Mater. Res. ,
2003,64(1) : 48—51
[107] Horinouchi H,Yamamoto H,Komatsu T,Huang Y B,Tsuchida
E,Kobayashi K. Cancer Sci. ,2008,99(6) :1274—1278
[108] Chang T M S. Blood Substitutes: Principles, Methods,
Products and Clinical Trials. Basel: Karger,1997

[1] Patricia A. Egner, Jin-Bing Wang, Yuan-Rong Zhu, Lisa P. Jacobson, Derek Ng, Alvaro Muñoz, Jed W. Fahey, Jian-Guo Chen, Tao-Yang Chen, Geng-Sun Qian, John D. Groopman, Thomas W. Kensler*. Prevention of Liver Cancer in Qidong, China:Lessons from Aflatoxin Biomarker Studies [J]. Progress in Chemistry, 2013, 25(09): 1454-1461.
[2] Yang Feng, Liang Hong*. Structural Basis of Human Serum Albumin and Its Complexes [J]. Progress in Chemistry, 2013, 25(04): 530-538.
[3] Zhang Jianjun, Gao Yuan, Sun Wanjin. Albumin as Drug Carriers [J]. Progress in Chemistry, 2011, 23(8): 1747-1754.