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Perfluorocarbon-based antidiabetic agents.

K L Kees1, T M Smith, M L McCaleb

  • 1Medicinal Chemistry Department, Wyeth-Ayerst Research, Princeton, New Jersey 08543-8000.

Journal of Medicinal Chemistry
|March 6, 1992
PubMed
Summary
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Perfluoro anilides, novel ciglitazone analogs, demonstrated oral antidiabetic activity in obese and diabetic mice. Structure-activity studies revealed that the perfluorocarbon chain length is crucial for antihyperglycemic effects.

Area of Science:

  • Medicinal Chemistry
  • Pharmacology
  • Endocrinology

Background:

  • Perfluoro-N-[4-(1H-tetrazol-5ylmethyl)phenyl]alkanamides (perfluoro anilides I) were previously identified as potential oral antidiabetic agents.
  • These compounds are novel analogues of ciglitazone, a known antidiabetic drug.
  • Non-insulin-dependent diabetes mellitus (NIDDM) animal models, specifically obese (ob/ob) and diabetic (db/db) mice, were used for preliminary evaluation.

Purpose of the Study:

  • To conduct a comprehensive structure-activity relationship (SAR) study of perfluoro anilides I.
  • To identify the key structural features responsible for the observed oral antidiabetic activity.
  • To optimize the chemical structure for enhanced antihyperglycemic efficacy.

Main Methods:

  • Screening of 86 perfluoro anilide analogues for blood glucose lowering effects in ob/ob mice.

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  • Utilizing a novel statistical procedure for comprehensive analysis across 140+ experiments (N=2966).
  • Evaluating the effect of perfluoro anilides I on plasma glucose and insulin levels in hyperglycemic and euglycemic animal models.

    • Main Results:

    • Perfluoro anilides I effectively lowered plasma glucose in hyperglycemic ob/ob and db/db mice, but not in normal rats.
    • Decreases in plasma insulin levels correlated with glucose reduction in hyperinsulinemic ob/ob mice.
    • Optimal antihyperglycemic activity was associated with medium-length perfluorocarbon (RF) chains, specifically C7 and C8, with C7F15 being particularly effective.

    Conclusions:

    • The lipophilic perfluorocarbon chain is the most critical structural determinant for antihyperglycemic activity in perfluoro anilides I.
    • Neither the phenyl nor the tetrazole rings are essential for the antihyperglycemic effect.
    • Medium-length (C7-C8) perfluorocarbon chains confer significant antihyperglycemic activity to diverse structures in the ob/ob mouse model.