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Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBHA.

Publication ,  Journal Article
Miranda, MT; Liddle, RA; Rivier, JE
Published in: J Med Chem
June 11, 1993

New analogues of human cholecystokinin in which the Tyr(SO3H) has been replaced by Phe(p-CH2SO3Na), methionines by norleucines, and tryptophan by 2-naphthylalanine([Phe(p-CH2- SO3Na)27,Nle28,31,Nal30]-CCK26-33 and [Phe(p-CH2SO3Na)27,Nle7,28,31,Nal30]-CCK-33) were synthesized by Fmoc solid phase methodology on two different resins (2,4- dimethoxybenzhydrylamine- and 4-(benzyloxy)-2',4'-dimethoxybenzhydrylamine resins, 2,4-DMBHA and TMBHA resins, respectively). While the syntheses on the TMBHA appeared to be more sluggish than those carried out on the 2,4-DMBHA, both final crude products were of equivalent relative purity and after purification gave approximately the same final yields of analogues estimated to have a purity greater than 93% using RPHPLC and CZE. The peptides were further characterized by amino acid analysis and LSIMS. Phe(p-CH2SO3Na)27,Nle7,28,31,Nal30]-CCK-33 was submitted to 33 Edman cycles and shown to be the desired product with less than 3% preview. Both analogues were tested for their ability to stimulate amylase release from isolated rat pancreatic acini. In this assay, [Phe(p-CH2SO3Na)27,Nle28,31,Nal30]-CCK26-33 and Phe(p-CH2SO3Na)27,Nle7,28,31,Nal30]-CCK-33 were 10 and 30 times less potent than CCK-8, respectively.

Duke Scholars

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

June 11, 1993

Volume

36

Issue

12

Start / End Page

1681 / 1688

Location

United States

Related Subject Headings

  • Sincalide
  • Resins, Plant
  • Rats
  • Pancreas
  • Molecular Sequence Data
  • Medicinal & Biomolecular Chemistry
  • Chromatography, High Pressure Liquid
  • Cholecystokinin
  • Benzhydryl Compounds
  • Animals
 

Citation

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Miranda, M. T., Liddle, R. A., & Rivier, J. E. (1993). Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBHA. J Med Chem, 36(12), 1681–1688. https://doi.org/10.1021/jm00064a001
Miranda, M. T., R. A. Liddle, and J. E. Rivier. “Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBHA.J Med Chem 36, no. 12 (June 11, 1993): 1681–88. https://doi.org/10.1021/jm00064a001.
Miranda MT, Liddle RA, Rivier JE. Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBHA. J Med Chem. 1993 Jun 11;36(12):1681–8.
Miranda, M. T., et al. “Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBHA.J Med Chem, vol. 36, no. 12, June 1993, pp. 1681–88. Pubmed, doi:10.1021/jm00064a001.
Miranda MT, Liddle RA, Rivier JE. Synthesis of human CCK26-33 and CCK-33 related analogues on 2,4-DMBHA and TMBHA. J Med Chem. 1993 Jun 11;36(12):1681–1688.
Journal cover image

Published In

J Med Chem

DOI

ISSN

0022-2623

Publication Date

June 11, 1993

Volume

36

Issue

12

Start / End Page

1681 / 1688

Location

United States

Related Subject Headings

  • Sincalide
  • Resins, Plant
  • Rats
  • Pancreas
  • Molecular Sequence Data
  • Medicinal & Biomolecular Chemistry
  • Chromatography, High Pressure Liquid
  • Cholecystokinin
  • Benzhydryl Compounds
  • Animals