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Cytotoxic activity and quantitative structure activity relationships of arylpropyl sulfonamides

Yu Jin Hwang1, Sang Min Park, Chul Bu Yim

  • 1College of Pharmacy, Chung-Ang University, Seoul 156-756, Korea.

The Korean Journal of Physiology & Pharmacology : Official Journal of the Korean Physiological Society and the Korean Society of Pharmacology
|June 19, 2013
PubMed

Insights

New arylpropyl sulfonamides, analogs of B13, show potent anticancer activity. Compound 15 demonstrated the strongest cytotoxicity against prostate cancer (PC-3) and leukemia (HL-60) cells, highlighting key structural features for enhanced efficacy.

Area of Science:

  • Medicinal Chemistry
  • Cancer Biology
  • Pharmacology

Background:

  • B13, a ceramide analog, is a known apoptosis inducer with significant cytotoxic effects.
  • Prostate cancer (PC-3) and leukemia (HL-60) are critical targets for novel therapeutic agents.

Purpose of the Study:

  • To synthesize and evaluate novel arylpropyl sulfonamide analogs of B13 for enhanced cytotoxic activity.
  • To identify key structural determinants responsible for the observed anticancer effects.

Main Methods:

  • Synthesis of arylpropyl sulfonamide analogs.
  • Cytotoxicity assessment using MTT assays in PC-3 and HL-60 cell lines.
  • Three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis using CoMSIA models.

Main Results:

  • Several compounds exhibited superior cytotoxicity compared to B13 in both cell lines.
  • Compound 15 displayed the most potent activity, with IC50 values of 29.2 µM (PC-3) and 20.7 µM (HL-60).
  • 3D-QSAR models showed high predictive power (q² = 0.816 and 0.702).

Conclusions:

  • Long alkyl chains and a specific stereochemistry (1R, 2R) of the propyl group are crucial for cytotoxic activity.
  • Incorporating small hydrophobic groups onto the phenyl and sulfonamide moieties can further enhance biological potency.
Keywords:
ArylpropanolCeramideCytotoxicityQSAR

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