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• W1971707858 abstract "Recent studies show that substitutions for the His in position 12 of bombesin (Bn) are important in determining antagonist activity. The present study was designed to investigate the chemical properties of the substitution in position 12 of Bn that determined antagonist activity and affinity. Nine [Leu14]Bn analogues with a single amino acid substitution and two analogues with multiple substitutions in addition to position 12 were synthesized. Replacing His12 with Phe12 resulted in an agonist with 100-fold decrease in potency and as reported previously, replacement with D-Phe12 resulted in an antagonist, but with a 10,000-fold decrease in affinity. Substitution of D-β-naphthylalanine (D-Nal12), a larger and more hydrophobic group than D-Phe, produced a complete loss of antagonist activity, whereas substitution of D-pyridylalanine (D-Pal12), a group more hydrophilic and similar in size to D-Phe, converted the analogue to a very weak agonist with 300-fold lower affinity than the D-Phe analogue. Antagonist activity depended on the nature of the aromatic moiety, with a D-Trp12 resulting in an inactive analogue, and with a D-Tyr12 resulting in a weak antagonist being 100-fold less potent than the D-Phe12 substitution. The addition of an electron withdrawing group to the D-Phe substitution (D-Cpa12) resulted in a minimal decrease in antagonist activity, whereas the addition of an electron donating group (p-hydroxy in D-Tyr12) resulted in a 30-fold decrease in antagonist activity. The addition of a basic group (D-Arg12 or D-Pal12) resulted in weak agonists. Substitution of D-Phe in position 5 or 6 and position 12 resulted in antagonists with the relative potency of [D-Phe6,D-Phe12,Leu14]Bn > [D-Phe5,D-Phe12,Leu14]Bn = [D-Phe12,Leu14]Bn. There was a close agreement between the ability of all analogues to affect biologic activity and inhibit 125I-[Tyr4]Bn binding. The present results indicate that the nature of the substitution in position 12 of Bn is critically important for determining antagonist activity and affinity. Stereospecificity of the substitution in position 12 is important in determining antagonist activity, whereas the hydrophilic nature of the aromatic moiety in the substitution is important in determining affinity of antagonists. Only a multiple D-Phe substitution (D-Phe6, D-Phe12) resulted in increasing antagonist activity by a factor of about 10-fold." @default.
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• W1971707858 date "1989-05-01" @default.
• W1971707858 modified "2023-10-18" @default.
• W1971707858 title "Effect of substitutions in position 12 of bombesin on antagonist activity" @default.
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• W1971707858 doi "https://doi.org/10.1016/0196-9781(89)90149-6" @default.
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