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. 2009 Nov 12;52(21):6519-22.
doi: 10.1021/jm9012856.

Gold(I) analogues of a platinum-acridine antitumor agent are only moderately cytotoxic but show potent activity against Mycobacterium tuberculosis

Lauren C Eiter  1 , Nathan W Hall, Cynthia S Day, Gilda Saluta, Gregory L Kucera, Ulrich Bierbach
Affiliations

Gold(I) analogues of a platinum-acridine antitumor agent are only moderately cytotoxic but show potent activity against Mycobacterium tuberculosis

Lauren C Eiter et al. J Med Chem. .

Abstract

Cationic gold(I) complexes containing 1-[2-(acridin-9-ylamino)ethyl]-1,3-dimethylthiourea (1), [AuL(1)](n+) (where L is Cl(-), Br(-), SCN(-), PEt(3), PPh(3), or 1), derived from a class of analogous platinum(II) antitumor agents, have been synthesized. Unlike platinum, gold does not form permanent adducts with DNA, and its complexes are 2 orders of magnitude less cytotoxic in non-small-cell lung cancer cells than the most active platinum-based agent. Instead, several gold analogues show submicromolar and selective antimicrobial activity against Mycobacterium tuberculosis.

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Figures

Scheme 1
Scheme 1
Synthesis of Gold–Acridine Derivatives 2–7.a a Reagents and conditions: (a) Tht, EtOH/H2O, 15 min, rt; (b) 1a or 1b, MeOH, 1 h, rt; (c) 1b, 2b, TlNO3, DMF, 16 h, rt; (d,e) 1. excess 47% HBr, NaOH, 5 d, 2. tht, MeOH, 1 h; (f) KSCN, H2O/CH2Cl2, 3 h, rt; (g) PEt3, EtOH, 1 h, rt, argon; (h,i) 1. AgNO3, DMF, 18 h, −45 °C, 2. 1b, DMF, 4 h, −45 → 25 °C; (j) PPh3, MeOH, 8 h, rt, argon; (k,l) 1. AgNO3, DMF, 18 h, −45 °C, 2. 1b, DMF, 4 h, −45 → 25 °C.
Chart 1
Chart 1
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References

    1. Kelland L. The resurgence of platinum-based cancer chemotherapy. Nat Rev Cancer. 2007;7:573–584. - PubMed
    1. Payne DJ. Microbiology. Desperately seeking new antibiotics. Science. 2008;321:1644–1645. - PubMed
    1. Ahmad S, Isab AA, Ali S, Al-Arfaj AR. Perspectives in bioinorganic chemistry of some metal based therapeutic agents. Polyhedron. 2006;25:1633–1645.
    1. Benedek TG. The history of gold therapy for tuberculosis. J Hist Med Allied Sci. 2004;59:50–89. - PubMed
    1. Shaw IC. Gold-based therapeutic agents. Chem Rev. 1999;99:2589–2600. - PubMed

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