Synthesis and biological activity of Substance P C‐terminal hexapeptide and heptapeptide analogues

GEORGE STAVROPOULOS; KOSTAS KARAGIANNIS; PAUL CORDOPATIS; DAVID HALLE; CHAIM GILON; GIORA BAR‐AKIVA; ZVI SELINGER; MICHAEL CHOREV

doi:10.1111/j.1399-3011.1991.tb00268.x

Synthesis and biological activity of Substance P C‐terminal hexapeptide and heptapeptide analogues

GEORGE STAVROPOULOS^*
, KOSTAS KARAGIANNIS
, PAUL CORDOPATIS
, DAVID HALLE
, CHAIM GILON
, GIORA BAR‐AKIVA
, ZVI SELINGER
, MICHAEL CHOREV

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

The analogues [Glu(OBzl)¹¹]SP_6–11 and [Glu(OBzl)¹¹]SP_5–11 of the C‐terminal hexapeptide and heptapeptide of Substance P have been synthesized by conventional solution methods. In each analogue the SCH₃ group of Met¹¹ is replaced by the COOCH₂C₆H₅ group. The in vitro activity of both analogues has been determined on three biological preparations: guinea pig ileum (GPI), rat vas deferens (RVD), and rat portal vein (RPV). The selectivity for the different receptors has been studied by utilizing atropine‐treated guinea pig ileum (GPI + At). The results showed that both analogues are mainly active on GPI through the NK‐1 receptor and that both analogues are equipotent to Substance P.

Original language	English
Pages (from-to)	180-184
Number of pages	5
Journal	International Journal of Peptide and Protein Research
Volume	37
Issue number	3
DOIs	https://doi.org/10.1111/j.1399-3011.1991.tb00268.x
State	Published - Mar 1991

Keywords

NK‐1 receptor
Substance P
Substance P C‐terminal analogues
guinea pig ileum assay
methionine replacement

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10.1111/j.1399-3011.1991.tb00268.x

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STAVROPOULOS, GEORGE., KARAGIANNIS, KOSTAS., CORDOPATIS, PAUL., HALLE, DAVID., GILON, CHAIM., BAR‐AKIVA, GIORA., SELINGER, ZVI., & CHOREV, MICHAEL. (1991). Synthesis and biological activity of Substance P C‐terminal hexapeptide and heptapeptide analogues. International Journal of Peptide and Protein Research, 37(3), 180-184. https://doi.org/10.1111/j.1399-3011.1991.tb00268.x

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title = "Synthesis and biological activity of Substance P C‐terminal hexapeptide and heptapeptide analogues",

abstract = "The analogues [Glu(OBzl)11]SP6–11 and [Glu(OBzl)11]SP5–11 of the C‐terminal hexapeptide and heptapeptide of Substance P have been synthesized by conventional solution methods. In each analogue the SCH3 group of Met11 is replaced by the COOCH2C6H5 group. The in vitro activity of both analogues has been determined on three biological preparations: guinea pig ileum (GPI), rat vas deferens (RVD), and rat portal vein (RPV). The selectivity for the different receptors has been studied by utilizing atropine‐treated guinea pig ileum (GPI + At). The results showed that both analogues are mainly active on GPI through the NK‐1 receptor and that both analogues are equipotent to Substance P.",

keywords = "NK‐1 receptor, Substance P, Substance P C‐terminal analogues, guinea pig ileum assay, methionine replacement",

author = "GEORGE STAVROPOULOS and KOSTAS KARAGIANNIS and PAUL CORDOPATIS and DAVID HALLE and CHAIM GILON and GIORA BAR‐AKIVA and ZVI SELINGER and MICHAEL CHOREV",

year = "1991",

month = mar,

doi = "10.1111/j.1399-3011.1991.tb00268.x",

language = "אנגלית",

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journal = "International Journal of Peptide and Protein Research",

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STAVROPOULOS, GEORGE, KARAGIANNIS, KOSTAS, CORDOPATIS, PAUL, HALLE, DAVID, GILON, CHAIM, BAR‐AKIVA, GIORA, SELINGER, ZVI & CHOREV, MICHAEL 1991, 'Synthesis and biological activity of Substance P C‐terminal hexapeptide and heptapeptide analogues', International Journal of Peptide and Protein Research, vol. 37, no. 3, pp. 180-184. https://doi.org/10.1111/j.1399-3011.1991.tb00268.x

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AU - STAVROPOULOS, GEORGE

AU - KARAGIANNIS, KOSTAS

AU - CORDOPATIS, PAUL

AU - HALLE, DAVID

AU - GILON, CHAIM

AU - BAR‐AKIVA, GIORA

AU - SELINGER, ZVI

AU - CHOREV, MICHAEL

PY - 1991/3

Y1 - 1991/3

N2 - The analogues [Glu(OBzl)11]SP6–11 and [Glu(OBzl)11]SP5–11 of the C‐terminal hexapeptide and heptapeptide of Substance P have been synthesized by conventional solution methods. In each analogue the SCH3 group of Met11 is replaced by the COOCH2C6H5 group. The in vitro activity of both analogues has been determined on three biological preparations: guinea pig ileum (GPI), rat vas deferens (RVD), and rat portal vein (RPV). The selectivity for the different receptors has been studied by utilizing atropine‐treated guinea pig ileum (GPI + At). The results showed that both analogues are mainly active on GPI through the NK‐1 receptor and that both analogues are equipotent to Substance P.

AB - The analogues [Glu(OBzl)11]SP6–11 and [Glu(OBzl)11]SP5–11 of the C‐terminal hexapeptide and heptapeptide of Substance P have been synthesized by conventional solution methods. In each analogue the SCH3 group of Met11 is replaced by the COOCH2C6H5 group. The in vitro activity of both analogues has been determined on three biological preparations: guinea pig ileum (GPI), rat vas deferens (RVD), and rat portal vein (RPV). The selectivity for the different receptors has been studied by utilizing atropine‐treated guinea pig ileum (GPI + At). The results showed that both analogues are mainly active on GPI through the NK‐1 receptor and that both analogues are equipotent to Substance P.

KW - NK‐1 receptor

KW - Substance P

KW - Substance P C‐terminal analogues

KW - guinea pig ileum assay

KW - methionine replacement

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JO - International Journal of Peptide and Protein Research

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IS - 3

ER -

Synthesis and biological activity of Substance P C‐terminal hexapeptide and heptapeptide analogues

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