Abstract
Substituted gold(III) tetraarylporphyrins have been synthesised. The analogues TPPAuCl (TPP = tetraphenylporhyrin), MeOTPPAuCl, TMOPPAuCl, MeO2CTPPAuCl, O2NTPPAuCl and PyTPPAuCl were evaluated for their in vitro cytotoxic activity against the Sarcoma 180 mouse tumour cell line panel. Compound MeO2CTPPAuCl exhibited good growth inhibitory properties against Sarcoma 180 and afforded IC50 values <3μM for 92.386% of the cell lines in the panel. Compounds MeOTPPAuCl and TPPAuCl were effective inhibitors of tumour cell growth, but generally less effective than MeO2CTPPAuCl as cytotoxic agents.
References
1.
Kovarik J.
,
Svec F.
, and
Thurzo V.
, Neoplasma , 1972 , 19 , 569 .
2.
Lippman A. J.
,
Helson C.
,
Helson L.
, and
Krakoff I. H.
, Cancer Chemother. Rep. , 1973 , 57 , 191 .
3.
Youn C.K.
,
Kim M.H.
,
Cho H.J.
, and
Kim H.B.
, Cancer Res. , 2004 , 64 , 4849 .
4.
Schenk P.W.
,
Brok M.
,
Boersma A.W.
, and
Brandsma J.A.
, Mol. Pharmacol. , 2003 , 64 , 259 .
5.
Shaw C.F.
, in:
Fricker S.P.
, (eds), Metal compounds in cancer therapy , Chapman and Hall , London , 1994 , pp. 46 –64 .
6.
Haiduc I.
, and
Silvestru C.
, In Vivo , 1989 , 3 , 285 .
7.
Sadler P. J.
,
Nasr M.
,
Narayanan V.L.
, Platinum coordination complexes in cancer chemotherapy , eds
Hacker M.P.
,
Douple E.B.
, and
Krakoff I.H.
, Martinus Nijhoff Publishing , Boston , 1984 , pp. 209 –304 .
8.
Shaw C.F.
III
, Chem. Rev. , 1999 , 99 , 2589 .
9.
Marcon G.
,
Messori L.
, and
Orioli P.
, Expert Rev Anticancer Ther. , 2002 , 2 , 337 .
10.
Marcon G.
,
Carotti S.
, and
Coronnello M.
, J. Med. Chem. , 2002 , 45 , 1672 .
11.
Tiekink E.R.
, Crit. Rev. Oncol. Hematol. , 2002 , 42 , 225 .
12.
Kean W.F.
,
Forestier F.
,
Kassam Y.
,
Buchanan W.W.
, and
Rooney P.J.
, Semin. Arthritis Rheum. , 1985 , 14 , 180 .
13.
Calamai P.
,
Carotti S.
, and
Guerri A.
, Anticancer Drug Des. , 1998 , 13 , 67 .
14.
Calamai P.
,
Carotti S.
, and
Guerri A.
, J. Inorg. Biochem. , 1997 , 66 , 103 .
15.
Cossu F.
,
Matovic Z.
,
Radanovic D.
, and
Ponticelli G.
, Farmaco , 1994 , 49 , 301 .
16.
Messori L.
,
Abbate F.
,
Marcon G.
,
Orioli P.
,
Fontani M.
,
Mini E.
,
Mazzei T.
,
Carotti S.
,
O'Connell T.
, and
Zanello P.
, J. Med. Chem. , 2000 , 43 , 3541 .
17.
Zhang C.X.
, and
Lippard S.J.
, Curr. Opin. Chem. Biol. , 2003 , 7 , 481 .
18.
Casini A.
,
Cinellu M.A.
,
Minghetti G.
,
Gabbiani C.
,
Coronnello M.
,
Mini E.
, and
Messori L.
, J. Med. Chem. , 2006 , 49 , 5524 .
19.
Coronnello M.
,
Mini E.
,
Caciagli B.
,
Cinellu M.A.
,
Bindoli A.
,
Gabbiani C.
, and
Messori L.
, J. Med. Chem. , 2005 , 48 , 6761 .
20.
Giovagnini L.
,
Ronconi L.
,
Aldinucci D.
,
Lorenzon D.
,
Sitran S.
, and
Fregona D.
, J. Med. Chem. , 2005 , 48 , 1588 .
21.
Kostova I.
, Anticancer Agents Med. Chem. , 2006 , 6 , 19 .
22.
Marcon G.
,
Carotti S.
,
Coronnello M.
,
Messori L.
,
Mini E.
,
Orioli P.
,
Mazzei T.
,
Cinellu M.A.
, and
Minghetti G.
, J. Med. Chem. , 2002 , 45 , 1672 .
23.
Marcon G.
,
Messori L.
,
Orioli P.
,
Cinellu M.A.
, and
Minghetti G.
, Eur. J. Biochem. , 2003 , 270 , 4655 .
24.
Messori L.
,
Abbate F.
,
Marcon G.
,
Orioli P.
,
Fontani M.
,
Mini E.
,
Mazzei T.
,
Carotti S.
,
O'Connell T.
, and
Zanello P.
, J. Med. Chem. , 2000 , 43 , 3541 .
25.
Messori L.
,
Orioli P.
,
Tempi C.
, and
Marcon G.
, Biochem. Biophys. Res. Commun. , 2001 , 281 , 352 .
26.
Ronconi L.
,
Giovagnini L.
,
Marzano C.
,
Bettio F.
,
Graziani R.
,
Pilloni G.
, and
Fregona D.
, Inorg. Chem. , 2005 , 44 , 1867 .
27.
Ronconi L.
,
Marzano C.
,
Zanello P.
,
Corsini M.
,
Miolo G.
,
Macca C.
,
Trevisan A.
, and
Fregona D.
, J. Med. Chem. , 2006 , 49 , 1648 .
28.
Sundriyal S.
,
Sharma R.K.
, and
Jain R.
, Curr. Med. Chem. , 2006 , 13 , 1321 .
29.
Che C.-M.
,
Sun R.W.-Y.
,
Yu W.-Y.
,
Ko C.-B.
,
Zhu N.
, and
Sun H.
, Chem. Commun. , 2003 , 1718 .
30.
Wang Y.
,
He Q.Y.
,
Sun R.W.
,
Che C.M.
, and
Chiu J.F.
, Cancer Res. , 2005 , 65 , 11553 .
31.
Lum C.T.
,
Yang Z.F.
, and
Li H.Y.
, Int. J. Cancer , 2006 , 118 , 1527 .
32.
Wang Y.
,
He Q.Y.
,
Che C.M.
, and
Chiu J.F.
, Proteomics , 2006 , 6 , 131 .
33.
Wang Y.
,
He Q.Y.
,
Sun R.W.-Y.
,
Che C.-M.
, and
Chiu J.-F.
, Eur. J. Pharm. , 2007 , 554 , 113 .
34.
Tu S.
,
Sun R.W.-Y.
,
Lin M.C.M.
,
Cui J.T.
,
Zou B.
,
Gu Q.
,
Kung H.-F.
,
Che C.-M.
, and
Wong B.C.Y.
, Cancer , 2009 , 4459 .
35.
To Y.F.
,
Sun R.W.-Y.
,
Chen Y.
,
Chan V.S.-F.
,
Yu W.-Y.
,
Tam P.K.-H.
,
Che C.-M.
, and
Lin C.-L.S.
, Int. J. Cancer , 2009 , 124 , 1971 .
36.
Che C.-M.
, and
Siu F.-M.
, Curr. Opin. Chem. Bio. , 2009 , 14 , 1 .
37.
Boudsocq F.
,
Benaim P.
,
Canitrot Y.
, Mol. Pharmacol. , 2005 , 67 , 1485 .
38.
Crooke S.T.
, and
Mirabelli C.K.
, Am. J. Med. , 1983 , 75 , 109 .
39.
Mirabelli C.K.
,
Johnson R.K.
,
Sung C.M.
,
Faucette L.
,
Muirhead K.
, and
Crooke S.T.
, Cancer Res. , 1985 , 45 , 32 .
40.
Wang Y.
,
He Q.-Y.
,
Che C.-M.
,
Tsao S.W.
,
Sun R.W.-Y.
, and
Chiu J.-F.
, Biochem. Pharm. , 2008 , 75 , 1282 .
41.
Chow K.H.M.
,
Sun R.W.Y.
,
Lam J.B.B.
,
Li C.K.L.
,
Xu A.
,
Ma D.L.
,
Abagyan R.
,
Wang Y.
, and
Che C.M.
, Cancer Res. , 2010 , 70 , 329 .
42.
Adler A.D.
,
Longo F.R.
,
Finarelli J.D.
,
Goldmacher J.
,
Assour J.
, and
Korsakoff L.
, J. Org. Chem. , 1967 , 32 , 476 .
43.
Lindsey J.S.
,
Schreiman I.C.
,
Hsu H.C.
,
Kearney P.C.
, and
Marguerettaz A.M.
, J. Org. Chem. , 1987 , 52 , 827 .
44.
Mosmann T.
, J. Immunol. Meth. , 1983 , 65 , 55 .
