Relationship between biological activity and dipole moment in benzo[a]phenothiazines

Noboru Motohashi, Teruo Kurihara, Wataru Yamanaka, Kazue Satoh, Hiroshi Sakagami, J. Molnár

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Relationship between the biological activity and two different dipole moments were investigated in 9 benzo[a]phenothiazines [1-8] by calculating the dipole moment with the PM3 method. 12H-Benzo[a]phenothiazine [1], 9-methyl-12H-benzo[a]phenothiazine [2], 10-methyl-12H-benzo[a]phenothiazine[3] and 11-methyl-12H-benzo[a]phenothiazine [4) induced monocytic differentiation of human myelogenous leukemic cell lines and displayed antitumor activity. These active compounds showed a significantly smaller value of calculated ground-state dipole moment (μ(g)) and larger value of first excited-state dipole moment (μ(e)). The μ(e)/μ(g) ratio of four active compounds [1-4] ranged from 3.25 to 4.38, whereas that of three inactive compounds [5,6,7] ranged from 1.77 to 2.72. These two different dipole moments might be useful parameters for estimation of the biological activity of benzo[a]phenothiazines [1-8].

Original languageEnglish
Pages (from-to)3431-3435
Number of pages5
JournalAnticancer Research
Volume17
Issue number5 A
Publication statusPublished - Sep 1997

Fingerprint

benzophenothiazine
Cell Line

Keywords

  • Antitumor activity
  • Benzo[a]phenothiazine
  • Differentiation
  • Dipole moment

ASJC Scopus subject areas

  • Cancer Research
  • Oncology

Cite this

Motohashi, N., Kurihara, T., Yamanaka, W., Satoh, K., Sakagami, H., & Molnár, J. (1997). Relationship between biological activity and dipole moment in benzo[a]phenothiazines. Anticancer Research, 17(5 A), 3431-3435.

Relationship between biological activity and dipole moment in benzo[a]phenothiazines. / Motohashi, Noboru; Kurihara, Teruo; Yamanaka, Wataru; Satoh, Kazue; Sakagami, Hiroshi; Molnár, J.

In: Anticancer Research, Vol. 17, No. 5 A, 09.1997, p. 3431-3435.

Research output: Contribution to journalArticle

Motohashi, N, Kurihara, T, Yamanaka, W, Satoh, K, Sakagami, H & Molnár, J 1997, 'Relationship between biological activity and dipole moment in benzo[a]phenothiazines', Anticancer Research, vol. 17, no. 5 A, pp. 3431-3435.
Motohashi N, Kurihara T, Yamanaka W, Satoh K, Sakagami H, Molnár J. Relationship between biological activity and dipole moment in benzo[a]phenothiazines. Anticancer Research. 1997 Sep;17(5 A):3431-3435.
Motohashi, Noboru ; Kurihara, Teruo ; Yamanaka, Wataru ; Satoh, Kazue ; Sakagami, Hiroshi ; Molnár, J. / Relationship between biological activity and dipole moment in benzo[a]phenothiazines. In: Anticancer Research. 1997 ; Vol. 17, No. 5 A. pp. 3431-3435.
@article{378331428b614b94a81e6277501a0a3f,
title = "Relationship between biological activity and dipole moment in benzo[a]phenothiazines",
abstract = "Relationship between the biological activity and two different dipole moments were investigated in 9 benzo[a]phenothiazines [1-8] by calculating the dipole moment with the PM3 method. 12H-Benzo[a]phenothiazine [1], 9-methyl-12H-benzo[a]phenothiazine [2], 10-methyl-12H-benzo[a]phenothiazine[3] and 11-methyl-12H-benzo[a]phenothiazine [4) induced monocytic differentiation of human myelogenous leukemic cell lines and displayed antitumor activity. These active compounds showed a significantly smaller value of calculated ground-state dipole moment (μ(g)) and larger value of first excited-state dipole moment (μ(e)). The μ(e)/μ(g) ratio of four active compounds [1-4] ranged from 3.25 to 4.38, whereas that of three inactive compounds [5,6,7] ranged from 1.77 to 2.72. These two different dipole moments might be useful parameters for estimation of the biological activity of benzo[a]phenothiazines [1-8].",
keywords = "Antitumor activity, Benzo[a]phenothiazine, Differentiation, Dipole moment",
author = "Noboru Motohashi and Teruo Kurihara and Wataru Yamanaka and Kazue Satoh and Hiroshi Sakagami and J. Moln{\'a}r",
year = "1997",
month = "9",
language = "English",
volume = "17",
pages = "3431--3435",
journal = "Anticancer Research",
issn = "0250-7005",
publisher = "International Institute of Anticancer Research",
number = "5 A",

}

TY - JOUR

T1 - Relationship between biological activity and dipole moment in benzo[a]phenothiazines

AU - Motohashi, Noboru

AU - Kurihara, Teruo

AU - Yamanaka, Wataru

AU - Satoh, Kazue

AU - Sakagami, Hiroshi

AU - Molnár, J.

PY - 1997/9

Y1 - 1997/9

N2 - Relationship between the biological activity and two different dipole moments were investigated in 9 benzo[a]phenothiazines [1-8] by calculating the dipole moment with the PM3 method. 12H-Benzo[a]phenothiazine [1], 9-methyl-12H-benzo[a]phenothiazine [2], 10-methyl-12H-benzo[a]phenothiazine[3] and 11-methyl-12H-benzo[a]phenothiazine [4) induced monocytic differentiation of human myelogenous leukemic cell lines and displayed antitumor activity. These active compounds showed a significantly smaller value of calculated ground-state dipole moment (μ(g)) and larger value of first excited-state dipole moment (μ(e)). The μ(e)/μ(g) ratio of four active compounds [1-4] ranged from 3.25 to 4.38, whereas that of three inactive compounds [5,6,7] ranged from 1.77 to 2.72. These two different dipole moments might be useful parameters for estimation of the biological activity of benzo[a]phenothiazines [1-8].

AB - Relationship between the biological activity and two different dipole moments were investigated in 9 benzo[a]phenothiazines [1-8] by calculating the dipole moment with the PM3 method. 12H-Benzo[a]phenothiazine [1], 9-methyl-12H-benzo[a]phenothiazine [2], 10-methyl-12H-benzo[a]phenothiazine[3] and 11-methyl-12H-benzo[a]phenothiazine [4) induced monocytic differentiation of human myelogenous leukemic cell lines and displayed antitumor activity. These active compounds showed a significantly smaller value of calculated ground-state dipole moment (μ(g)) and larger value of first excited-state dipole moment (μ(e)). The μ(e)/μ(g) ratio of four active compounds [1-4] ranged from 3.25 to 4.38, whereas that of three inactive compounds [5,6,7] ranged from 1.77 to 2.72. These two different dipole moments might be useful parameters for estimation of the biological activity of benzo[a]phenothiazines [1-8].

KW - Antitumor activity

KW - Benzo[a]phenothiazine

KW - Differentiation

KW - Dipole moment

UR - http://www.scopus.com/inward/record.url?scp=0030778440&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030778440&partnerID=8YFLogxK

M3 - Article

C2 - 9413182

AN - SCOPUS:0030778440

VL - 17

SP - 3431

EP - 3435

JO - Anticancer Research

JF - Anticancer Research

SN - 0250-7005

IS - 5 A

ER -