中文
Earlier issues
Announcement
More
Progress in Chemistry 2006, Vol. 18 Issue (09): 1101-1109 Previous Articles   Next Articles

• Review •

NO Releasing Diazeniumdiolates and Targeting NO Releasing Materials

Qun Gao;Ajun Wan**   

  1. Department of Chemistry, School of Chemistry and Chemical Technology, Shanghai Jiaotong University, Shanghai 200240, China
  • Received: Revised: Online: Published:
  • Contact: Ajun Wan
PDF ( 1317 ) Cited
Export

EndNote

Ris

BibTeX

Chemical structures and properties of diazeniumdiolates that make them so excellent for designing materials capable of targeting reliable and controllable fluxes of bioactive NO have become one of the forefronts and highlights of novel NO donors. The toxicity and poor biocompatibility of the nucleophile (polyamines) and the formation of potentially carcinogenic nitrosoamine are the problems associated with its successful clinical application. Recent research progress on targeting nitric oxide releasing materials is reviewed , basing on the three strategies of delivering NO specifically to a targeted site , including polymer-based diazeniumdiolates , enzyme activated diazeniumdiolates and photosensitive diazeniumdiolates.
Key words: nitric oxide, NO donor, diazeniumdiolates, nucleophiles, targeting NO release

CLC Number: 

[ 1 ] Furchgott R F , Zawakzki J V. Nature. , 1980 , 288 : 373 —376
[ 2 ] Murad F. Angew. Chem. Int . Ed. , 1999 , 38 : 1857 —1868
[ 3 ] Ignarro L J . Angew. Chem. Int . Ed. , 1999 , 38 : 1882 —1892
[ 4 ] Bredt D S , Snyder S H. Annu. Rev. Biochem. , 1994 , 63 :175 —195
[ 5 ] Umans J G, Levi R. Annu. Rev. Physiol . , 1995 , 57 : 771 —790
[ 6 ] Lloyd-Jones D M, Bloch K D. Annu. Rev. Med. , 1996 , 47 :365 —375
[ 7 ] Koshland D E. Science , 1992 , 258 : 1861 —1861
[ 8 ] Napoli C , Ignarro L J . Annu. Rev. Pharmacol . Toxicol . , 2003 ,43 : 97 —123
[ 9 ] Drago R S , Paulik F E. J . Am. Chem. Soc. , 1960 , 82 : 96 —98
[10] Drago R S , Karstetter B R. J . Am. Chem. Soc. , 1961 , 83 :1819 —1822
[11] Drago R S , Ragsdale R O , Eyman D P. J . Am. Chem. Soc. ,1961 , 83 : 4337 —4339
[12] Ragsdale R O , Karstetter B R , Drago R S. Inorg. Chem. , 1965 ,4 : 420 —422
[13] Maragos C M, Morley D , Keefer L K, et al . J . Med. Chem. ,1991 , 34 : 3242 —3247
[14] Keefer L K, Flippen-Anderson J L , George C , et al . Nitric Oxide : Biol . Chem. , 2001 , 5 : 377 —394
[15] Hrabie J A , Keefer L K. Chem. Rev. , 2002 , 102 : 1135 —1154
[16] Arnold E V , Citro M L , Hrabie J A. Nitric Oxide : Biol . Chem. ,2002 , 7 : 103 —108
[17] Hrabie J A , Arnold E V , Citro M L , et al . J . Org. Chem. ,2000 , 65 : 5745 —5751
[18] Hrabie J A , Citro M L , Chmurny G N , et al . J . Org. Chem. ,2005 , 70 : 7647 —7653
[19] Saavedra J E , Dunams T M, Flippen-Anderson J L , et al . J .Org. Chem. , 1992 , 57 : 6134 —6138
[20] Taylor D K, Bytheway I , Hall M B , et al . J . Org. Chem. ,1995 , 60 : 435 —444
[21] Morely D , Keefer L K. J . Cardiovasc. Pharm. , 1993 , 22 : S3 —S9
[22] Smith D J , Chakravarthy D , Keefer L K, et al . J . Med. Chem. ,1996 , 39 : 1148 —1156
[23] Davies K M, Wink D A , Saavedra J E , et al . J . Am. Chem.Soc. , 2001 , 123 : 5473 —5481
[24] Hrabie J A , Klose J R , Wink D A , et al . J . Org. Chem. , 1993 ,58 : 1472 —1476
[25] Reynolds M M, Zhou Z , Meyerhoff M E , et al . Org. Lett . ,2005 , 7 : 2813 —2816
[26] Keefer L K. Annu. Rev. Pharmacol . Toxicol . , 2003 , 43 : 585 —607
[27] Showalter B M, Reynolds M M, Keefer L K, et al . J . Am.Chem. Soc. , 2005 , 127 : 14188 —14189
[28] Saavedra J E , Billiar T R , Keefer L K, et al . J . Med. Chem. ,1997 , 40 : 1947 —1954
[29] Liu J , Waalkes M P. Toxicology , 2005 , 208 : 289 —297
[30] Saavedra J E , Shami P J , Keefer L K, et al . J . Med. Chem. ,2000 , 43 : 261 —269
[31] Wu X J , Tang X P , Wang P G, et al . Tetrahedron Lett . , 2001 ,42 : 3779 —3782
[32] Frost M C , Reynolds M M, Meyerhoff M E. Biomaterials , 2005 ,26 : 1685 —1693
[33] Davies M, Fulton G, Hagen P. Brit . J . Surg. , 1995 , 82 :1598 —1610
[34] Moncada S , Higgs E. FASEB J . , 1995 , 9 : 1319 —1330
[35] Srinivasan A , Kebede N , Toscano J P , et al . J . Am. Chem.Soc. , 2001 , 123 : 5465 —5472
[36] Zhang H P , Annich G M, Meyerhoff M E , et al . Biomaterials ,2002 , 23 : 1485 —1494
[37] Nablo B J , Chen T Y, Schoenfisch M H. J . Am. Chem. Soc. ,2001 , 123 : 9712 —9713
[38] Robbins M E , Schoenfisch M H. J . Am. Chem. Soc. , 2003 ,125 : 6068 —6069
[39] Marxer S M, Rothrock A R , Schoenfisch M H , et al . Chem.Mater. , 2003 , 15 : 4193 —4199
[40] Robbins M E , Hopper E D , Schoenfisch M H. Langmuir , 2004 ,20 : 10296 —10302
[41] Nablo B J , Schoenfisch M H. Biomacromolecules , 2004 , 5 :2034 —2041
[42] Nablo B J , Schoenfisch M H. Biomaterials , 2005 , 26 : 4405 —4415
[43] Roselle D C , Smith DJ . J . Control . Rel . , 1998 , 51 : 131 —142
[44] Wink D A , Vodovotz Y, Laval J , et al . Carcinogenesis , 1998 ,19 : 711 —721
[45] Mowery K A , Schoenfisch M H , Meyerhoff M E , et al .Biomaterials , 2000 , 21 : 9 —21
[46] Parzuchowski P G, Frost M C , Meyerhoff M E. J . Am. Chem.Soc. , 2002 , 124 : 12182 —12191
[47] Zhang H P , Annich GM, Meyerhoff M E , et al . J . Am. Chem.Soc. , 2003 , 125 (17) : 5015 —5024
[48] Masters K S. Ph. D Dissertation of Rice University , USA , 2002
[49] Jun HW, Taite L J , West J L. Biomacromolecules , 2005 , 6(2) :838 —844
[50] Zhou Z R , Meyerhoff M E. Biomaterials , 2005 , 26 : 6506 —6517
[51] Zhou Z R , Meyerhoff M E. Biomacromolecules , 2005 , 6 : 780 —789
[52] Putnam D , Langer R. Macromolecules , 1999 , 32 : 3658 —3662
[53] Godkey W T , Wu K K, Mikos A G. Biomaterials , 2001 , 22 :471 —480
[54] Choksakulnimitr S , Masudas S , Hashida M, et al . J . Control .Rel . , 1995 , 34 : 233 —241
[55] Serhatkulu S. Ph. D Dissertation of the University of Akron , USA ,1999
[56] Smith D J , Serhatkulu S. US 6 261 594 , 2001
[57] Smith D J , Yazici S. US 6 451 337 , 2002
[58] Makings L R , Tsien R Y. J . Biol . Chem. , 1994 , 269 : 6282 —6285
[59] Ruane P H , Bushan K M, Toscano J P , et al . J . Am. Chem.Soc. , 2002 , 124 : 9806 —9811
[60] Bushan K M, Xu H , Toscano J P , et al . J . Am. Chem. Soc. ,2002 , 124 : 12640 —12641
[61] Pavlos C M, Xu H , Toscano J P. Free Radical Bio. Med. ,2004 , 37 : 745 —752
[1] Wendi Guo, Ye Liu. Carbonylation of Alkynes with Different Nucleophiles Catalyzed By Transition Metal Complexes [J]. Progress in Chemistry, 2021, 33(4): 512-523.
[2] Hanqiang Zhou, Mingfei Yu, Qiaoshan Chen, Jianchun Wang, Jinhong Bi. Synthesis, Modification of Bismuth Oxyiodide Photocatalyst for Purification of Nitric Oxide [J]. Progress in Chemistry, 2021, 33(12): 2404-2412.
[3] Shi Ting, Chen Ming, Chen Xiongping, Wang Jitao, Wan Ajun, Zhao Yi-Lei. Molecular Mechanism of Protein S-Nitrosylation and Its Correlation with Human Diseases [J]. Progress in Chemistry, 2015, 27(5): 594-600.
[4] Jing Xiaotong, Yu Fabiao, Chen Lingxin. Fluorescent Probes for Reactive Nitrogen Species [J]. Progress in Chemistry, 2014, 26(05): 866-878.
[5] Lin Yingwu. Computer-Aided Rational Protein Design: From Myoglobin to Nitric Oxide Reductases [J]. Progress in Chemistry, 2012, 24(05): 784-789.
[6] Zhang Dengqing*|Zhao Shengyin|Liu Haixiong. Fluorescent Probes for Sensing Nitric Oxide [J]. Progress in Chemistry, 2008, 20(09): 1396-1405.
[7] Kou Yuxia| Wan Ajun**. Preparation of NO releasing Polymers and Their Applications for Biomedical Devices [J]. Progress in Chemistry, 2008, 20(05): 729-739.
[8] Hailing Li Huibi Xu Zhonghong Gao . Biological Microelement Iron and Protein Tyrosine Nitration [J]. Progress in Chemistry, 2006, 18(05): 622-626.