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Volumn 8, Issue 1, 2006, Pages 7-10

Design and synthesis of a quinazolinone natural product-templated library with cytotoxic activity

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; QUINAZOLINE DERIVATIVE;

EID: 31544457663     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050108g     Document Type: Article
Times cited : (75)

References (35)
  • 1
    • 7744242263 scopus 로고    scopus 로고
    • For recent reviews on quinazoline alkaloids, see: (a) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650.
    • (2004) Nat. Prod. Rep. , vol.21 , pp. 650
    • Michael, J.P.1
  • 2
    • 84945434219 scopus 로고
    • Ansell, M. F., Ed.; Supplements to the 2nd ed.; Elsevier: Amsterdam
    • (b) Johne, S. In Rodd's Chemistry of Carbon Compounds; Ansell, M. F., Ed.; Supplements to the 2nd ed.; Elsevier: Amsterdam, 1995; Vol. IV I/J, pp 223-240.
    • (1995) Rodd's Chemistry of Carbon Compounds , vol.4 , Issue.I-J , pp. 223-240
    • Johne, S.1
  • 12
    • 31544466988 scopus 로고    scopus 로고
    • note
    • For example, Raltitrexed (Tomudex, marketed for colorectal cancer), Ispinesib (phase II for solid tumors), and Tempostatin (phase II for bladder cancer).
  • 20
    • 31544441306 scopus 로고    scopus 로고
    • in press
    • Wilson, C. J.; Si, Y.; Thompson, C. M.; Smellie, A.; Ashwell, M.; Liu, J.-F.; Ye, P.; Yohannes, D.; Ng, S.-C. J. Biomol. Screening 2005, in press. MTS assay was performed as described in Promega Technical Bulletin No. 169 (CellTiter 96 Aqueous Non-Radioactive Cell Proliferation Assay, http://www.promega.com/; Website accessed July 28, 2005.). The assay uses the novel tetrazolium compound (3-(4,5-dimethylthiazol-2-yl)-5-(3- carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, inner salt; MTS) and the electron coupling reagent phenazine methosulfate (PMS). MTS is chemically reduced by cells into formazan, which is soluble in tissue culture medium. The measurement of the absorbance of the formazan can be carried out using 96-well microplates at 492 nm. The assay measures dehydrogenase enzyme activity found in metabolically active cells.
    • (2005) J. Biomol. Screening
    • Wilson, C.J.1    Si, Y.2    Thompson, C.M.3    Smellie, A.4    Ashwell, M.5    Liu, J.-F.6    Ye, P.7    Yohannes, D.8    Ng, S.-C.9
  • 28
    • 31544464572 scopus 로고    scopus 로고
    • note
    • Both mackinazolinone (5) and isaindigotone (6) only demonstrated cytotoxicity at > 100 μM concentrations in the selected cancer cell lines in the MTS assay described above. For primary screening, our activity cutoff was ≤50 μM.
  • 29
    • 31544443173 scopus 로고    scopus 로고
    • Philadelphia, PA, August 22-26, CINF-98
    • The in-house-developed library design tool we employed, MAPMAKER, has been described; see: (a) Li, D.; Rotstein, S. Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, August 22-26, 2004, CINF-98.
    • (2004) Abstracts of Papers, 228th ACS National Meeting
    • Li, D.1    Rotstein, S.2
  • 32
    • 31544461722 scopus 로고    scopus 로고
    • note
    • We employed a Biotage Smith Synthesizer integrated into the ArQule AMAP high-throughput parallel chemistry platform.
  • 33
    • 0035165945 scopus 로고    scopus 로고
    • The purification of crude products were performed on the Preparative HPLC. The preparative HPLCs were conducted using a ProntoSIL 120-10-C18 column (50 × 20 mm). The flow rate was at 40 mL/min utilizing an acetonitrile/water mobile phase and 0.1% trifluoroacetic acid as a modifier with mass-triggered fraction collection. The crude and purified products were characterized by LC/MS with an integrated LC/MS system of a Shimadzu LC instrument and Micromass DMZ MS instrument. The HPLC was conducted using a Zorbax SB-C8 column (4.6 × 30 mm 3.5μm) with a flow rate at 3.0 mL/min, an acetonitrile/water mobile phase, and 0.05% trifluoroacetic acid as a modifier. For detailed information, see: (a) Kyranos, J. N.; Cai, H.; Zhang, B.; Goetzinger, W. K. Curr. Opin. Drug Discovery Dev. 2001, 4, 719.
    • (2001) Curr. Opin. Drug Discovery Dev. , vol.4 , pp. 719
    • Kyranos, J.N.1    Cai, H.2    Zhang, B.3    Goetzinger, W.K.4
  • 35
    • 31544450470 scopus 로고    scopus 로고
    • note
    • The three cancer cell lines represent diverse tissue sources. Two sets of assays (n = 2) were run with 20 data points using Taxol as a positive control.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.