Relationship between electronic structure and cytotoxic activity of tropolones

In Vivo

Volumn 20, Issue 3, 2006, Pages 391-396

  Kurihara, Teruo ^a   Mine, Hiroko ^a   Satoh, Yoshimasa ^a   Wakabayashi, Hidetsugu ^a   Motohashi, Noboru ^b   Sakagami, Hiroshi ^c  

^a JOSAI UNIVERSITY   (Japan)

^b MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^c MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

Author keywords

Cytotoxic activity; Dipole moment ( ); PM3 calculation method; Tropolones

Indexed keywords

2 METHOXYTROPONE; 2,4,6 TRIBROMO 7 METHOXYTROPONE; 2,7 DIBROMOTROPONE; CYTOTOXIC AGENT; TROPOLONE; TROPOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL LINE; CYTOTOXICITY; DIPOLE; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROPHOBICITY; MULTIPLE LINEAR REGRESSION ANALYSIS; PARTITION COEFFICIENT; PHASE TRANSITION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION;

EID: 33646842665     PISSN: 0258851X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Nozoe T, Takase K, Matsumura H, Asao T, Kikuchi K and Ito S: Non-benzenoid aromatic compounds. In: Dai-Yuki Kagaku. Kotake M (ed.). Asakura-Shoten. Tokyo (in Japanese). Vol. 13, pp. 1-656, 1960.
2. Nozoe T, Breslow R, Hafner K, Ito S and Murata I (eds.): Topics in Nonbenzenoid Aromatic Chemistry. Hirokawa Publ Co., Tokyo (in Japanese). Vol. I. pp. 1-295, 1973.
3. Nozoe T, Breslow R, Hafner K, Ito S and Murata I (eds.): Topics in Nonbenzenoid Aromatic Chemistry. Hirokawa Publ Co., Tokyo (in Japanese). Vol. II, pp. 1-379, 1977.
4. Inamori Y, Shinohara S, Tsujibo H, Okabe T, Morita Y, Sakagami Y, Kumeda Y and Ishida N: Antimicrobial activity and metalloprotease inhibition of Hinokitiol-related compounds, the constituents of Thujopsis dolabrata S. and Z. hondai Mak. Biol Pharm Bull 22: 990-993, 1999.
5. Inamori Y, Sakagami Y, Morita Y, Shibata M, Sugiura M, Kumeda Y, Okabe T, Tsujibo H and Ishida N: Antifungal activity of Hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities. Biol Pharm Bull 23: 995-997, 2000.
6. Inamori Y, Nishiguchi K, Matsuo N, Tsujibo H, Baba K and Ishida N: Phytogrowth-inhibitory activities of tropolone and Hinokitiol. Chem Pharm Bull 39: 2378-2381, 1991.
7. Sakagami Y, Inamori Y, Isoyama N, Tsujibo H, Okabe T, Morita Y and Ishida N: Phytogrowth-inhibitory activities of β-dolabrin and γ-thujaplicin, Hinokitiol-related compounds and constituents of Thujopsis dolabrata Sieb. et Zucc. var hondai Makino. Biol Pharm Bull 23: 645-648, 2000.
8. Inamori Y, Tsujibo H, Ohnishi H, Ishii F, Mizugaki M, Aso H and Ishida N: Cytotoxic effect of Hinokitiol and tropolone on the growth of mammalian cells and on blastogenesis of mouse splenic T cells. Biol Pharm Bull 16: 521-523, 1993.
9. Matsumura E, Morita Y, Date T, Tsujibo H, Yasuda M, Okabe T, Ishida N and Inamori Y: Cytotoxicity of the Hinokitiol-related compounds, γ-thujaplicin and β-dolabrin. Biol Pharm Bull 24: 299-302, 2001.
10. Borchardt RT: Catechol O-methyltransferase. 1. Kinetics of tropolone inhibition. J Medic Chem 16: 377-382, 1973.
11. Wakabayashi H, Yokoyama K, Hashiba K, Hashimoto K, Kikuchi H, Nishikawa H, Kurihara T, Satho K, Shioda S, Muto S, Terakubo S, Nakashima H, Motohashi N and Sakagami H: Cytotoxic activity of tropolones against human oral tumor cell lines. Anticancer Res 23: 4757-4764, 2003.
12. PM3 semi-empirical MO calculations were performed by MOPAC version 6 on an Intellistation M Pro personal computer.
13. Ohkura K and Hori H: Analysis of structure-permeability correlation of nitrophenol analogs in newborn rat abdominal skin using semiempirical molecular orbital calculation. Bioorg Med Chem 7: 309-314, 1998.
14. Kurihara T, Yamada T, Yamamoto A, Kawase M, Motohashi N, Sakagami H and Molnar J: Relationship between electronic structure and cytotoxic activity of dopamine and 3-benzazepine derivatives. In Vivo 18: 443-448, 2004.
15. Kurihara T, Noguchi M, Noguchi T, Wakabayashi H, Motohashi N and Sakagami H: Relationship between electronic structure and cytotoxic activity of azulenes. In Vivo 20: 385-390, 2006.