Structure/activity correlations for auxins

Acta Botanica Croatica

Volumn 58, Issue , 1999, Pages 27-37

  Kojić Prodić, Biserka ^a   Magnus, Volker ^a   Antolić, Snježana ^a   Tomić, Sanja ^a   Salopek Sondi, Branka ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Auxin; Indole 3 acetic acid; Molecular recognition; QSAR; Quantitative structure activity relationship; Similarity analysis

Indexed keywords

EID: 0007992658     PISSN: 03650588     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. ANTOLIĆ, S., KOJIĆ-PRODIĆ, B., TOMIĆ, S., NIGOVIĆ, B., MAGNUS, V., COHEN, J. D., 1996: Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (auxin). Acta Crystallogr. B52, 651-661.
2. ANTOLIĆ, S., SALOPEK, B., KOJIĆ-PRODIĆ, B., MAGNUS, V., COHEN, J. D., 1999: Structural characterization and auxin properties of dichlorinated indole-3-acetic acids. Plant Growth Regul. 27, 21-31.
3. BURES, M.G., BLACK-SCHAEFER, C., GARDNER, G., 1991: The discovery of novel auxin transport inhibitors by molecular modelling and three-dimensional pattern analysis. J. Computer-Aided Mol. Design 5, 323-334.
4. BÖHM, H.-J., KLEBE, G., KUBINYI, H. (eds.), 1996: Wirkstoffdesign. Spektrum, Akademischer Verlag, Heidelberg.
5. CHANDRASEKHAR, K., RAGHUNATHAN, S., 1982: A reinvestigation of the structure of (3-indolyl)acetic acid. Acta Crystallogr. B38, 2534-2535.
6. EDGERTON, M.D., TROPSHA, A., JONES, A.M., 1994: Modelling the auxin-binding site of auxin-binding protein 1 of maize. Phytochemistry 35, 1111-1123.
7. FISCHER, E., 1894: Einfluss der Confǐguration auf die Wirkung der Enzyme. Ber. Dtsch. Chem. Ges. 27, 2985-2993.
8. GSCHWEND, D.A., GOOD, A.C., KUNTZ, J.D., 1996: Molecular docking towards drug discovery. J. Mol. Recognition 9, 175-186.
9. HATANO, T., KATAYAMA, M., MARUMO, S., 1987: 5,6-Dichloroindole-3-acetic acid as a potent auxin: its synthesis and biological activity. Experientia 43, 1237-1239.
10. HATANO, T., KATO, Y., KATAYAMA, M., MARUMO, S., 1989: A new antiauxin, α-(5,7-dichloroindole-3-)isobutyric acid: its chemical synthesis and biological activity. Experientia 45, 400-402.
11. JÖNSSON, Å. 1961: Chemical structure and growth activity of auxins and antiauxins. In: RUHLAND, W. (ed.), Encyclopedia of Plant Physiology, vol. 14, 960-1006. Springer-Verlag, Berlin.
12. KAETHNER, J.M., 1977: Conformational change theory for auxin structure-activity relationship. Nature 267, 19-23.
13. KARLE, I.L., BRITTS, K., GUM, P., 1964: Crystal and molecular structure of 3-indolylacetic acid. Acta Crystallogr. 17, 496-499.
14. KATEKAR, G.F., 1979: Auxins: on the nature of the receptor site and molecular requirements for auxin activity. Phytochemistry 18, 223-233.
15. KOJIĆ-PRODIĆ, B., NIGOVIĆ, B., TOMIĆ, S., ILIĆ, N., MAGNUS, V., KONJEVIĆ, R., GIBA, Z., DUAX, W.L., 1991: Structural studies on 5-(n-alkyl)-substituted derivatives of the plant hormone, indol-3-ylacetic acid. Acta Crystallogr. B47, 1010-1019.
16. KOSHLAND, D., JR., 1994: The key-lock theory and the induced fit theory. Angew. Chem. Int. Ed. Engl. 33, 2375-2378.
17. KUBINYI, H. (ed.), 1993: 3D QSAR in Drug Design. ESCOM, Leiden.
18. MCRAE, D.H., BONNER, J., 1952: Diortho substituted phenoxyacetic acids as antiauxins. Plant Physiol. 27, 834-838.
19. NAPIER, R.M., 1995: Towards an understanding of ABP1. J. Exp. Botany 46, 1787-1795.
20. NAPIER, R.M., VENIS, M.A., 1995: Auxin action and auxin-binding proteins. New Phytol. 129, 167-201.
21. NIGOVIĆ, B., ANTOLIĆ, S., KOJIĆ-PRODIĆ, B., KIRALJ, R., MAGNUS, V., SALOPEK-SONDI, B., 1999: Correlation of structural and physico-chemical parameters with the bioactivity of alkylated derivatives of indole-3-acetic acid, a phytohormone (auxin). Acta Crystallogr. B55, in press.
22. NIGOVIĆ, B., KOJIĆ-PRODIĆ, B., ANTOLIĆ, S., TOMIĆ, S., PUNTAREC, V., COHEN, J.D., 1996: Structural studies on monohalogenated derivatives of the phytohormone indole-3-acetic acid (auxin). Acta Crystallogr. B52, 332-343.
23. RAKHAMINOVA, A. B., KHAVKIN, E. E., YAGUZHINSKY, L. S., 1978: Postroenie modeli retseptora auksinov. Biokhimiya 43, 806-823.
24. RAMEK, M., TOMIĆ, S., 1998 a: RHF Conformational analysis of the auxin phytohormones n-ethyl-indole-3-acetic acid (n=4,5,6). Int. J. Quantum Chem.-Quantum Biology Symposium 70, 1169-1175.
25. RAMEK, M., TOMIĆ, S., 1998 b: Ab initio RHF investigation of mono- and dichlorinated indole-3-acetic acid (IAA) phytohormones. J. Mol. Struct. (Theochem.) 454, 167-173.
26. RAMEK, M., TOMIĆ, S., KOJIĆ-PRODIĆ, B., 1995: Systematic ab initio SCF conformational analysis of indol-3-ylacetic acid phytohormone (auxin): comparison with experimental and molecular mechanics calculations. Int. J. Quantum Chem. 22, 75-81.
27. RAMEK, M., TOMIĆ, S., KOJIĆ-PRODIĆ, B., 1996: Comparative ab initio SCF conformational study of 4-chloro-indole-3-acetic acid and indole-3-acetic acid phytohormones (auxins). Int. J. Quantum Chem. 23, 3-9.
28. RAY, P.M., DOHRMANN, U., HERTEL, R., 1977: Specificity of auxin-binding sites on maize coleoptile membranes as possible receptor sites for auxin action. Plant Physiol. 60, 585-591.
29. RUBERY, P.H., 1987: Auxin transport. In: DAVIES, P.J. (ed.), Plant hormones and their role in plant growth and development, 341-362. Martinus Nijhoff Publishers, Dordrecht.
30. SCHNEIDER, E.A., WIGHTMAN, F., 1978: Auxins. In: LETHAM, D.S., GOODWIN, T.W., HIGGINS, T.J.V. (eds.), Phytohormones and related compounds - a comprehensive treatise, vol. 1, 29-105. Elsevier, Amsterdam.
31. THIMANN, K.V., 1977: Hormone action in the whole life of plants. The University of Massachusetts Press, Amherst.
32. TOMIĆ, S., GABDOULLINE, R.R., KOJIĆ-PRODIĆ, B., WADE, R., 1998 a: Classification of auxin plant hormones by interaction property similarity indices. J. Computer-Aided Mol. Design 12, 63-79.
33. TOMIĆ, S., RAMEK, M., KOJIĆ-PRODIĆ, B., 1998 b: Combined ab initio SCF and molecular mechanics studies of propionic and isobutyric acids and their indole derivatives related to the phytohormone auxin (indole-3-acetic acid). Croat. Chem. Acta 71, 511-525.
34. TUOMINEN, H., PUECH, L., FINK, S., SUNDBERG, B., 1997: A radial concentration gradient of indole-3-acetic acid is related to secondary xylem development in hybrid aspen. Plant Physiol. 115, 577-585.
35. UGGLA, C., MELLEROWICZ, E.J., SUNDBERG, B., 1998: Indole-3-acetic acid controls cambial growth in Scots pine by positional signaling. Plant Physiol. 117, 113-121.
36. VENIS, M.A., NAPIER, R.M., 1995: Auxin receptors and auxin binding proteins. Crit. Rev. Plant Sci. 14, 27-47.