Replacement of the carboxylic acid group of prostaglandin F with a hydroxyl or methoxy substituent provides biologically unique compounds

Article date: August 2000

By: D F Woodward, A H‐P Krauss, J Chen, D W Gil, K M Kedzie, C E Protzman, L Shi, R Chen, H A Krauss, A Bogardus, H T T Dinh, L A Wheeler, S W Andrews, R M Burk, T Gac, M B Roof, M E Garst, L J Kaplan, G Sachs, K L Pierce, J W Regan, R A Ross, M F Chan in Volume 130, Issue 8, pages 1933-1943

Replacement of the carboxylic acid group of PGF with the non‐acidic substituents hydroxyl (‐OH) or methoxy (‐OCH3) resulted in an unexpected activity profile.

Although PGF 1‐OH and PGF 1‐OCH3 exhibited potent contractile effects similar to 17‐phenyl PGF in the cat lung parenchymal preparation, they were approximately 1000 times less potent than 17‐phenyl PGF in stimulating recombinant feline and human FP receptors.

In human dermal fibroblasts and Swiss 3T3 cells PGF 1‐OH and PGF 1‐OCH3 produced no Ca2+ signal until a 1 μM concentration was exceeded. Pretreatment of Swiss 3T3 cells with either 1 μM PGF 1‐OH or PGF 1‐OCH3 did not attenuate Ca2+ signal responses produced by PGF or fluprostenol. In the rat uterus, PGF 1‐OH was about two orders of magnitude less potent than 17‐phenyl PGF whereas PGF 1‐OCH3 produced only a minimal effect.

Radioligand binding studies on cat lung parenchymal plasma membrane preparations suggested that the cat lung parenchyma does not contain a homogeneous population of receptors that equally respond to PGF1‐OH, PGF1‐OCH3, and classical FP receptor agonists.

Studies on smooth muscle preparations and cells containing DP, EP1, EP2, EP3, EP4, IP, and TP receptors indicated that the activity of PGF 1‐OH and PGF 1‐OCH3 could not be ascribed to interaction with these receptors.

The potent effects of PGF 1‐OH and PGF 1‐OCH3 on the cat lung parenchyma are difficult to describe in terms of interaction with the FP or any other known prostanoid receptor.

Replacement of the carboxylic acid group of PGF with the non‐acidic substituents hydroxyl (‐OH) or methoxy (‐OCH3) resulted in an unexpected activity profile.

Although PGF 1‐OH and PGF 1‐OCH3 exhibited potent contractile effects similar to 17‐phenyl PGF in the cat lung parenchymal preparation, they were approximately 1000 times less potent than 17‐phenyl PGF in stimulating recombinant feline and human FP receptors.

In human dermal fibroblasts and Swiss 3T3 cells PGF 1‐OH and PGF 1‐OCH3 produced no Ca2+ signal until a 1 μM concentration was exceeded. Pretreatment of Swiss 3T3 cells with either 1 μM PGF 1‐OH or PGF 1‐OCH3 did not attenuate Ca2+ signal responses produced by PGF or fluprostenol. In the rat uterus, PGF 1‐OH was about two orders of magnitude less potent than 17‐phenyl PGF whereas PGF 1‐OCH3 produced only a minimal effect.

Radioligand binding studies on cat lung parenchymal plasma membrane preparations suggested that the cat lung parenchyma does not contain a homogeneous population of receptors that equally respond to PGF1‐OH, PGF1‐OCH3, and classical FP receptor agonists.

Studies on smooth muscle preparations and cells containing DP, EP1, EP2, EP3, EP4, IP, and TP receptors indicated that the activity of PGF 1‐OH and PGF 1‐OCH3 could not be ascribed to interaction with these receptors.

The potent effects of PGF 1‐OH and PGF 1‐OCH3 on the cat lung parenchyma are difficult to describe in terms of interaction with the FP or any other known prostanoid receptor.

British Journal of Pharmacology (2000) 130, 1933–1943; doi:10.1038/sj.bjp.0703462

DOI: 10.1038/sj.bjp.0703462

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