Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity

Derin C. D'Amico; Toshi Aya; Jason Human; Christopher Fotsch; Jian Jeffrey Chen; Kaustav Biswas; Bobby Riahi; Mark H. Norman; Christopher A. Willoughby; Randall Hungate; Paul J. Reider; Gloria Biddlecome; Dianna Lester-Zeiner; Carlo Van Staden; Eileen Johnson; Augustus Kamassah; Leyla Arik; Judy Wang; Vellarkad N. Viswanadhan; Robert D. Groneberg; James Zhan; Hideo Suzuki; Andras Toro; David A. Mareska; David E. Clarke; Darren M. Harvey; Laurence E. Burgess; Ellen R. Laird; Benny Askew; Gordon Ng

doi:10.1021/jm061224g

Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity

Derin C. D'Amico
, Toshi Aya
, Jason Human
, Christopher Fotsch
, Jian Jeffrey Chen
, Kaustav Biswas
, Bobby Riahi
, Mark H. Norman
, Christopher A. Willoughby
, Randall Hungate
, Paul J. Reider
, Gloria Biddlecome
, Dianna Lester-Zeiner
, Carlo Van Staden
, Eileen Johnson
, Augustus Kamassah
, Leyla Arik
, Judy Wang
, Vellarkad N. Viswanadhan
, Robert D. Groneberg

James Zhan, Hideo Suzuki, Andras Toro, David A. Mareska, David E. Clarke, Darren M. Harvey, Laurence E. Burgess, Ellen R. Laird, Benny Askew, Gordon Ng

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

23 Scopus citations

Abstract

We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed ∼30% of the gained affinity between "flexible" 4 (K_i = 132 nM) and "rigid" 28 (K_i = 0.77 nM) to decreased conformational entropy.

Original language	English (US)
Pages (from-to)	607-610
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	50
Issue number	4
DOIs	https://doi.org/10.1021/jm061224g
State	Published - Feb 22 2007
Externally published	Yes

All Science Journal Classification (ASJC) codes

Drug Discovery
Molecular Medicine

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10.1021/jm061224g

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D'Amico, D. C., Aya, T., Human, J., Fotsch, C., Chen, J. J., Biswas, K., Riahi, B., Norman, M. H., Willoughby, C. A., Hungate, R., Reider, P. J., Biddlecome, G., Lester-Zeiner, D., Van Staden, C., Johnson, E., Kamassah, A., Arik, L., Wang, J., Viswanadhan, V. N., ... Ng, G. (2007). Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity. Journal of Medicinal Chemistry, 50(4), 607-610. https://doi.org/10.1021/jm061224g

@article{64a17b4db9f64404ad5e28a8b2021662,

title = "Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity",

abstract = "We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed ∼30\% of the gained affinity between {"}flexible{"} 4 (Ki = 132 nM) and {"}rigid{"} 28 (Ki = 0.77 nM) to decreased conformational entropy.",

author = "D'Amico, \{Derin C.\} and Toshi Aya and Jason Human and Christopher Fotsch and Chen, \{Jian Jeffrey\} and Kaustav Biswas and Bobby Riahi and Norman, \{Mark H.\} and Willoughby, \{Christopher A.\} and Randall Hungate and Reider, \{Paul J.\} and Gloria Biddlecome and Dianna Lester-Zeiner and \{Van Staden\}, Carlo and Eileen Johnson and Augustus Kamassah and Leyla Arik and Judy Wang and Viswanadhan, \{Vellarkad N.\} and Groneberg, \{Robert D.\} and James Zhan and Hideo Suzuki and Andras Toro and Mareska, \{David A.\} and Clarke, \{David E.\} and Harvey, \{Darren M.\} and Burgess, \{Laurence E.\} and Laird, \{Ellen R.\} and Benny Askew and Gordon Ng",

year = "2007",

month = feb,

day = "22",

doi = "10.1021/jm061224g",

language = "English (US)",

volume = "50",

pages = "607--610",

journal = "Journal of Medicinal Chemistry",

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D'Amico, DC, Aya, T, Human, J, Fotsch, C, Chen, JJ, Biswas, K, Riahi, B, Norman, MH, Willoughby, CA, Hungate, R, Reider, PJ, Biddlecome, G, Lester-Zeiner, D, Van Staden, C, Johnson, E, Kamassah, A, Arik, L, Wang, J, Viswanadhan, VN, Groneberg, RD, Zhan, J, Suzuki, H, Toro, A, Mareska, DA, Clarke, DE, Harvey, DM, Burgess, LE, Laird, ER, Askew, B & Ng, G 2007, 'Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity', Journal of Medicinal Chemistry, vol. 50, no. 4, pp. 607-610. https://doi.org/10.1021/jm061224g

TY - JOUR

T1 - Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity

AU - D'Amico, Derin C.

AU - Aya, Toshi

AU - Human, Jason

AU - Fotsch, Christopher

AU - Chen, Jian Jeffrey

AU - Biswas, Kaustav

AU - Riahi, Bobby

AU - Norman, Mark H.

AU - Willoughby, Christopher A.

AU - Hungate, Randall

AU - Reider, Paul J.

AU - Biddlecome, Gloria

AU - Lester-Zeiner, Dianna

AU - Van Staden, Carlo

AU - Johnson, Eileen

AU - Kamassah, Augustus

AU - Arik, Leyla

AU - Wang, Judy

AU - Viswanadhan, Vellarkad N.

AU - Groneberg, Robert D.

AU - Zhan, James

AU - Suzuki, Hideo

AU - Toro, Andras

AU - Mareska, David A.

AU - Clarke, David E.

AU - Harvey, Darren M.

AU - Burgess, Laurence E.

AU - Laird, Ellen R.

AU - Askew, Benny

AU - Ng, Gordon

PY - 2007/2/22

Y1 - 2007/2/22

N2 - We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed ∼30% of the gained affinity between "flexible" 4 (Ki = 132 nM) and "rigid" 28 (Ki = 0.77 nM) to decreased conformational entropy.

AB - We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed ∼30% of the gained affinity between "flexible" 4 (Ki = 132 nM) and "rigid" 28 (Ki = 0.77 nM) to decreased conformational entropy.

UR - https://www.scopus.com/pages/publications/33847414932

UR - https://www.scopus.com/pages/publications/33847414932#tab=citedBy

U2 - 10.1021/jm061224g

DO - 10.1021/jm061224g

M3 - Article

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AN - SCOPUS:33847414932

SN - 0022-2623

VL - 50

SP - 607

EP - 610

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 4

ER -

Identification of a nonpeptidic and conformationally restricted bradykinin B1 receptor antagonist with anti-inflammatory activity

Abstract

All Science Journal Classification (ASJC) codes

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