Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluation of their anti-inflammatory activity

Padmanabha V. Kattamuri; Rebecca Salmonsen; Catherine McQuain; Sumner Burstein; Hao Sun; Guigen Li

doi:10.1016/j.lfs.2012.06.040

Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluation of their anti-inflammatory activity

Padmanabha V. Kattamuri, Rebecca Salmonsen, Catherine McQuain, Sumner Burstein, Hao Sun, Guigen Li

Chemistry and Biochemistry

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

1 Scopus citations

Abstract

Aims: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluate their analgesic and anti-inflammatory potential. Main methods: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Δ^13,14-PGJ₂ (PGJ) are measured by ELISA following LPS (10 ng/ml) stimulation and treatment with 0.1, 0.3, 1.0, 3.0 and 10 μM concentrations of the compounds. Key findings: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis). Significance: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain.

Original language	English
Pages (from-to)	506-511
Number of pages	6
Journal	Life Sciences
Volume	92
Issue number	8-9
DOIs	https://doi.org/10.1016/j.lfs.2012.06.040
State	Published - Mar 19 2013

Keywords

15-Deoxy-Δ -PGJ (PGJ) stimulation
Anandamide
Apoptosis
Arachidonyl amide
Cannabinoid receptor

Access to Document

10.1016/j.lfs.2012.06.040

Cite this

@article{fa878521f7c94b55a3e07691353ebc67,

title = "Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluation of their anti-inflammatory activity",

abstract = "Aims: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluate their analgesic and anti-inflammatory potential. Main methods: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Δ13,14-PGJ2 (PGJ) are measured by ELISA following LPS (10 ng/ml) stimulation and treatment with 0.1, 0.3, 1.0, 3.0 and 10 μM concentrations of the compounds. Key findings: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis). Significance: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain.",

keywords = "15-Deoxy-Δ -PGJ (PGJ) stimulation, Anandamide, Apoptosis, Arachidonyl amide, Cannabinoid receptor",

author = "Kattamuri, {Padmanabha V.} and Rebecca Salmonsen and Catherine McQuain and Sumner Burstein and Hao Sun and Guigen Li",

note = "Funding Information: This publication was made possible by grant R03DA026960 from the National Institute on Drug Abuse and the National Institutes of Health grant R21DA031860-01 , Bethesda, MD. Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the National Institute on Drug Abuse and the National Institutes of Health. ",

year = "2013",

month = mar,

day = "19",

doi = "10.1016/j.lfs.2012.06.040",

language = "English",

volume = "92",

pages = "506--511",

journal = "Life Sciences",

issn = "0024-3205",

number = "8-9",

}

TY - JOUR

T1 - Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluation of their anti-inflammatory activity

AU - Kattamuri, Padmanabha V.

AU - Salmonsen, Rebecca

AU - McQuain, Catherine

AU - Burstein, Sumner

AU - Sun, Hao

AU - Li, Guigen

N1 - Funding Information: This publication was made possible by grant R03DA026960 from the National Institute on Drug Abuse and the National Institutes of Health grant R21DA031860-01 , Bethesda, MD. Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the National Institute on Drug Abuse and the National Institutes of Health.

PY - 2013/3/19

Y1 - 2013/3/19

N2 - Aims: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluate their analgesic and anti-inflammatory potential. Main methods: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Δ13,14-PGJ2 (PGJ) are measured by ELISA following LPS (10 ng/ml) stimulation and treatment with 0.1, 0.3, 1.0, 3.0 and 10 μM concentrations of the compounds. Key findings: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis). Significance: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain.

AB - Aims: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluate their analgesic and anti-inflammatory potential. Main methods: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Δ13,14-PGJ2 (PGJ) are measured by ELISA following LPS (10 ng/ml) stimulation and treatment with 0.1, 0.3, 1.0, 3.0 and 10 μM concentrations of the compounds. Key findings: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis). Significance: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain.

KW - 15-Deoxy-Δ -PGJ (PGJ) stimulation

KW - Anandamide

KW - Apoptosis

KW - Arachidonyl amide

KW - Cannabinoid receptor

UR - http://www.scopus.com/inward/record.url?scp=84874651560&partnerID=8YFLogxK

U2 - 10.1016/j.lfs.2012.06.040

DO - 10.1016/j.lfs.2012.06.040

M3 - Article

C2 - 22820546

AN - SCOPUS:84874651560

VL - 92

SP - 506

EP - 511

JO - Life Sciences

JF - Life Sciences

SN - 0024-3205

IS - 8-9

ER -

Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluation of their anti-inflammatory activity

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this