Preliminary Studies on the Antitumor Metal2Based Drugs Basing on TCM Active Ingredients

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1 PROGRESS IN CHEMISTRY Vol. 21 No. 5 May, ( ) DNA, : O614 ; R914 ; R97911 : A : X(2009) Preliminary Studies on the Antitumor Metal2Based Drugs Basing on TCM Active Ingredients Chen Zhenfeng 3 3 Peng Yan Tan Mingxiong Liu Yancheng Wang Hengshan Liang Hong 3 3 ( The Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China, School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin , China) Abstract The preliminary studies on the antitumor metal2based drugs basing on TCM active ingredients are reviewed. The studies on the synthesis, structure, antitumour activity and interaction with DNA of metal complexes with TCM active ingredients, alkaloids, flavonoids, quinones and cantharidin, coumarins, plumbagin as well as camphoic acid. The future development of metal2based antitumour drugs basing on TCM active ingredients is prospected. Key words traditional Chinese medicine ( TCM) ; active ingredients ; metal complexes ; antitumour Contents 1 Alkaloid2metal complexes with antitumour activity 2 Flavonoid2metal complexes with antitumour activity 3 Quinone2metal complexes with antitumour activity 4 Other active components metal complexes with antitumour activity 5 Concluding remarks 1967, [1 5 ] 30,, 30 [6 ],,,,, [7 ],,,,,,,, : ( ) 3 ( No , , ) 973 ( No. 2007CB516805, 2009CB526503) 3 3 e2mail com

2 [8,9 ], DNA ; DNA,,, [11,12 ] 1. 2 Fe Ga Au Sn Cu, ( 2) Sn Cu Cis2[ Pt (L) Cl 2 ] cis2[ Pt (L) (DMSO) Cl 2 ] [11 ] [10 ] Pt Au Ru Zn Ag Mo Fe Mn Co Cu Sn Cu Sm 20, Pt Au Ru Zn Fe Mn Co Cu Sm 10 ( 1) Pt Ru Au Ag Mo Zn Co, Ag SGC BEL , Fig. 1 Crystal structures of cis2[ Pt (L) Cl 2 ] and cis2[ Pt (L) (DMSO) Cl 2 ] [11 ] 2 [ Sn ( H2MT) Cl 5 ] [ Cu ( H2MT) 2 O 3 ] (ClO 4 ) 4 [14 ] Fig. 2 Crystal structures of [ Sn ( H2MT) Cl 5 ] and [ Cu ( H2 MT) 2 O 3 ] (ClO 4 ) 4 [14 ], Fe Ga Au,, Fe NCIH460 Ketr23 CNE1 Hep G2 SW %,5811 %,62151 %,5914 %,64154 % [13 ] ; Ga NCIH460 Hep G2 SW %,71143 %,99136 % ; Au Ketr23, MCF27 CNE1 Hela Hep G2, %, %,70195 %,8015 %,86141 % ; Sn Ketr23 SW480, % % ; Cu

3 gπml SK2OV % DNA, DNA [14 ] 1. 3 Al2Allaf [15 ] (harmine) Pd ( ) [ Pd (harmine) Cl 2 DMSO], P388, L1210 K562, [ Pd (harmine) Cl 2 DMSO ],, 52 2 (flavonoids), [16 ], ; ;, [9 ] ( ) ( ) Hep22, BHK22, BHK221 HL260, ( ) [17 ] La (chrysin) 2 (OAc) 7H 2 O A2549 P388, 10 M, 7315 %,4214 %, (419 %,1617 %) [18 ], DNA, DNA DNA, Cu ( ),Co ( ),Ni ( ),Zn ( ), 3,, CD ct2dna [19 ] Hep G2 SGC7901 CNE1 Hela Ketr23 Hep G2 Ketr3 CNE1 10 M, 50 %,, TCM,, Kosmider [20 ] (flavone) 3,, { cis2bis ( 32aminoflavone ) dichloro2platinum ( ) } ( 3),MTT,32 A549 L1210, 3 cis2bis (32aminoflavone) dichloroplatinum ( ) [20 ] Fig. 3 Molecular structure of cis2bis ( 32aminoflavone ) dichloroplatinum( ) [20 ] 3 (Adriamycin),, Cu ( ),Fe ( ), [21 ],,,Chen [22 ] (NQTS) Cu ( ), Ni ( ),Pd ( ), SRB,Ni2 NQTS MCF27 ( IC M), 3182 M 4 411

4 932 21, Kostova [23 ] La ( ),Ce ( ),Nd ( ), IR 1 H 13 C NMR, MTT K2562 and LAMA284 Egan Ag( ) : IC 50, ;, DNA [24 ] 412 (cantharidin), Ho [ Pt ( C 8 H 8 O 5 ) (NH 2 R) 2 ] ( 4) TCM2Pt SK2Hep21 ( ),, PP2A ( 2A) DNA [25 ], [26 28 ] 4 ( ) Fig. 4 [ Pt (C 8 H 8 O 5 ) (NH 2 R) 2 ] (1 5) Ga ( ) La ( ),, [29 ] 413 [30 ], 20, 6 ( 5), Cu Co Ni Zn Mn Ca Mg Na La Nd Y Dy Sm Gd Er 5 [ Cu(Pln) 2 ] [ Cu ( Pln) (bpy) H 2 O ] 2 (NO 3 ) 2 [30 ] Fig. 5 Crystal structures of [ Cu (Pln) 2 ] and [ Cu (Pln) (bpy) H 2 O] 2 (NO 3 ) 2 [30 ],,,,, 10 gπml, 3 ( KB ( ) KBV200 ( ) MDA2MB2231 ( ) ) % % % % % 7312 %, % % % 10, Cu Co Ni Zn La Y, (TOPO ), 1156 M, TOPO DNA ; 25 M, [ Cu (Pln) 2 ] TOPO DNA

5 Pt ( ) 8 ( )2 Pt ( ) ( 6), HL260, 3AO, BEL27402, A549 ; 1,, [31 ] 6 21 R,2 R2 2 Pt ( ) [31 ] Fig. 6 trans21 R, 2 R2Diaminocyclohexane complex [31 ] 5 camphorato2pt,,,, TCM2 [ 1 ] Rosenberg B, Camp L V, Trosko J E, Mansour V H. Nature,1969, 222 : [ 2 ] Orvig C, Abrams M J. Chem. Rev., 1999, 99 : [ 3 ] Clarke M J, Zhu F, Frasca D R. Chem. Rev., 1999, 99 : [ 4 ] Wong E, Giandomenico C M. Chem. Rev., 1999, 99 : [ 5 ] Jamieson E, Lippard S J. Chem. Rev., 1999, 99 : [ 6 ] (Wang L H), (Liu Y), ( You Q D), ( Gou S H). (Progress in Chem. ), 2004, 16 (3) : [ 7 ] (Xu G), (Cui Y B), (Cui K), ( Gou S H). (Progress in Chem. ), 2006, 18 (1) : [ 8 ] (Tan M X), (Chen Z F), (Liang H). (Chemistry and Industry of Forest Products), 2008, 28 (6) : [ 9 ] (Zhong D C), (Zhang S F), (Chen Z F), ( Wang H S), (Liang H). ( Chemical World), 2006, (9) : [10 ] (Liu Y C). (Doctor Dissertation of Nankai University), 2007 [11 ] Chen Z F, Liu Y C, Liu L M, et al. Dalton Trans., 2009, (2) : [12 ] (Liu H G), (Qin S H), (Liu L M), (Wang B L), (Liu Y C), (Chen Z F). ( Chinese Pharmacological Bulletin), 2008, 24 ( 11) : [13 ] (Mao L), (Liu L M), (Liu Y C), (Chen Z F), (Liu H G), (Liang H). (J. Guangxi Normal University (Natural Science Edition) ), 2008, 26 (2) : [14 ] (Mao L), (Master Dissertation of Guangxi Normal University), 2008 [15 ] Al2Allaf T A K, Rashan L J. Eur. J. Med. Chem., 1998, 33 : [16 ] Hodek P, Trefil P, Stiborov M. Chemico2Biological Interactions, 2002, 139 : 1 21 [17 ] Zhang Q, Wang L, Liu X, et al. Transition Met. Chem., 1996, 21 : [18 ] Zeng Y B, Yang N, Liu W S, Tang N. J. Inorgan. Biochem., 2003, 97 : [19 ] (Zhu J C). ( Master Dissertation of Guangxi Normal University), 2008 [20 ] Kosmider B, Osiecka R. Drug Development Research, 2004, 63 : [21 ] Min F, Yang Y L, He P G, et al. Spectrochimica Acta Part A, 2000, 56 : [22 ] Chen J, Huang Y, Liu G. Toxicolog. Appl. Pharmacolog., 2004, 197 : [23 ] Kostova I, Momekov G. Eur. J. Med. Chem., 2006, 41 : [24 ] Thati B, Noble A, Egan D A, et al. Cancer Letters, 2007, 248 : [25 ] Ho Y P, To K K, Au2Yeung S C F, et al. J. Med. Chem., 2001, 44 : [26 ] Wang X, Au2Yeung S C F, Ho Y P. J. Inorg. Biochem., 2007, 101 : [27 ] To K K W, Wang X, Yu C W, Ho Y P, Au2Yeung S C F. Bioorgan. Med. Chem., 2004, 12 : [28 ] Yu C W, Li K K W, Pang S K, Au2Yeung S C F, Ho Y P. Bioorgan. Med. Chem. Lett., 2006, 16 : [29 ] Yin F L, Zou J J, Xu L, et al. J. Rare Earths, 2005, 23 : [30 ] (Tan M X). (Doctor Dissertation of Central2South University), 2008 [31 ] Wang L, Gou S, Chen Y, Liu Y. Bioorgan. &Med. Chem. Lett., 2005, 15 :

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