Biopolym. Cell. 2010; 26(1):62-71.
Molecular Biophysics
Study of IR spectrum of the testosterone and ethyniltestosterone by quantum-chemical density functional theory
1Minaeva V. A., 1Minaev B. F., 1Kapinus S. S.
  1. B. Khmelnyckyy Cherkasy National University
    81, Shevchenko Blvd., Cherkassy, Ukraine, 18031


Aim. To perform full assignment of IR spectra of steroid hormones, testosterone and ethyniltestosterone and to connect vibrational frequency and intensity of IR absorption bands with the peculiarities of electronic structure and geometry of the above hormones. Methods. Calculations of vibrational frequency and intensity of IR bands of testosterone and ethyniltestosterone are performed using the density functional theory within the B3LYP/6-31G** approach with a complete geometry optimization by the gradient method. Results. Complete assignment of IR absor- ption bands of testosterone and ethyniltestosterone is performed. Conclusions. For the first time the frequencies and normal modes of vibrations are predicted in the low-frequency region of the IR spectrum. Biological importance of the obtained results is discussed.
Keywords: testosterone, ethyniltestosterone, quantum-chemical density functional theory, vibrational IR spectra


[1] Sergeev P. V. Steroid hormones Moscow: Nauka, 1984 240 p.
[2] Meynuoring C. Mechanism of androgens action Moscow: Mir, 1972 224 p.
[3] Kushlinskij N. E., Degtjar V. G. Metabolism and mechanism of androgens action Moscow: RAMS, 2005 182 p.
[4] Kulinskij B. I. Transfer and transduction of hormone signal to different cell compartments. Soros Education J. 1997; N 8 P. 14–19.
[5] Bursi R., Groen M. Application of (quantitative) structureactivity relationships to progestagenes: from serendipity to structure-based design. Eur. J. Med. Chem 2000 35, N 9 P. 787–796 .
[6] Minaev B. F., Minaeva V. A., Pristupa R. M. Geometry and electronic structure study of testosterone, 17-methyl testosterone and ethysterone by density functional method Visn. Cherkas. State Univ. Technol 2006; N 2 P. 134–140.
[7] Becke A. Density-functional thermochemistry. The role of exact exchange J. Chem. Phys 1993 98, N 7 P. 5648– 5655.
[8] Lee C., Yang W., Parr R. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev 1988 37, N 2 P. 785–789.
[9] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery Jr., J. A., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian, H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R. L., Fox D. J., Keith T., Al-Laham M. A., Peng C. Y., Nanayakkara A., Challacombe M., Gill P. M. W., Johnson B., Chen W., Wong M. W., Gonzalez C., Pople J. A. Gaussian 03, Revision C.02 Wallingford CT: Gaussian Inc., 2004.
[10] Minaev B. F., Minaeva V. A. Study of IR spectrum of the 17-estradiol by quantum-chemical density functional theory. Biopolym. Cell. 2006 22, N 5 P. 363–374.
[11] Bellamy LJ. The infra-red spectra of complex molecules. London : Methuen New York : Wiley, 1958.
[12] (National Institute of Advanced Industrial Science and Technology, date of access).
[13] Pat. 2009147 Russian Federation, C07J9/00. N 4908998/04; appl. 08.02.1991. H-phosphonates of hydroxyl-containg steroids as reagents for solid state synthesis of steroid derivatives of oligonucleotides or their analogous / A. G. Venjaminova, Z. A. Sergeeva, V. Z. Bashirova (The patent owner Novosibirsk Institute of Bioorganic Chemistry SB RAS) Publ. 15.03.1994.
[14] Kubli-Garfias C. Ab initio comparative study of the electronic structure of testosterone, epitestosterone and androstendione. J. Mol. Struct. (Theochem) 1998 422, N 1–3 P. 167–177.
[15] Minaeva V. A., Minaev B. F., Hovorun D. N. Vibrational spectra of the steroid hormones, estradiol and estriol, calculated by density functional theory. The role of low-frequency vibrations. Ukr Biokhim Zh. 2008 80, N 4 P. 82–95.