Authors:
Sandra Šegan Technology and Metallurgy Institute of Chemistry Njegoševa 12 11000 Belgrade Serbia

Search for other papers by Sandra Šegan in
Current site
Google Scholar
PubMed
Close
,
Dejan Opsenica Technology and Metallurgy Institute of Chemistry Njegoševa 12 11000 Belgrade Serbia

Search for other papers by Dejan Opsenica in
Current site
Google Scholar
PubMed
Close
,
Bogdan Šolaja University of Belgrade Faculty of Chemistry P.O. Box 51 11158 Belgrade Serbia

Search for other papers by Bogdan Šolaja in
Current site
Google Scholar
PubMed
Close
, and
Dušanka Milojković-Opsenica University of Belgrade Faculty of Chemistry P.O. Box 51 11158 Belgrade Serbia

Search for other papers by Dušanka Milojković-Opsenica in
Current site
Google Scholar
PubMed
Close
Restricted access

Seven pairs of cis-trans isomers of bis-steroidal tetraoxanes have been examined by both normal-phase (NP) and reversed-phase (RP) planar chromatography. Unmodified silica gel was used with ethyl acetate-toluene and ethyl acetate-petroleum ether as mobile phases in typical normal-phase systems. CN-silica with the mobile phases methanol-water and acetone-water and RP-18 silica with water-organic modifier (methanol, acetone, or dioxane) mobile phases were used as reversed-phase systems. For the RP systems a good linear correlation was established between RM values and amount ([%] ν/ν ) of organic modifier in the mobile phase (usually r > 0.99). It was found that under both NP and RP conditions cis isomers were more weakly retained than the corresponding trans isomers. The only exception to this was the chromatographic behavior of C(24) methyl esters. It was established that increasing the polarity of substituents at C(24) and C(24a) led to stronger retention in NP systems, i.e. weaker retention in RP systems. Highly selective separation was achieved in all the chromatographic systems investigated. Possible separation mechanisms are discussed on the basis of the results obtained.

  • X.X. Zhu, M. Nichifor , Acc. Chem. Res. 35 (2002) 539–546.

    Nichifor M. , '' (2002 ) 35 Acc. Chem. Res. : 539 -546 .

  • D.B. Salunke, B.G. Hazra, V.S. Pore, M.K. Bhat, P.B. Nahar, M.V. Deshpande , J. Med. Chem. 47 (2004) 1591–1594.

    Deshpande M.V. , '' (2004 ) 47 J. Med. Chem. : 1591 -1594 .

  • P.L. Anelli, L. Lattuada, V. Lorusso, G. Lux, A. Morisetti, P. Morosini, M. Serleti, F. Uggeri , J. Med. Chem. 47 (2004) 3629–3641.

    Uggeri F. , '' (2004 ) 47 J. Med. Chem. : 3629 -3641 .

  • A. Kannan, E. De Clercq, C. Pannecouque, M. Witvrouw, T.L. Hartman, J.A. Turpin, R.W. Buckheit, M. Cushman , Tetrahedron 57 (2001) 9385–9391.

    Cushman M. , '' (2001 ) 57 Tetrahedron : 9385 -9391 .

  • B. Natalini, R. Sardella, E. Camaioni, S. Natalini, R. Pellicciari , Chromatographia 64 (2006) 343–349.

    Pellicciari R. , '' (2006 ) 64 Chromatographia : 343 -349 .

  • S. Scalia , J. Chromatogr. B 671 (1995) 299–317.

    Scalia S. , '' (1995 ) 671 J. Chromatogr. B : 299 -317 .

  • A. Baeyer, V. Villiger , Chem. Ber. 33 (1900) 2479.

    Villiger V. , '' (1900 ) 33 Chem. Ber. : 2479 -.

  • A. Rieche, R. Meister, Chem. Ber. 72 (1939) 1933.

    Meister R. , '' (1939 ) 72 Chem. Ber. : 1933 -.

  • J.L. Vennerstrom, H. Fu, N. Ellis, W.Y. Ager, A.L. Wood Jr, S.L. Andersen, L. Gerena , and W.K. Milhous , J. Med. Chem. 35 (1992) 3023–3027.

    Milhous W.K. , '' (1992 ) 35 J. Med. Chem. : 3023 -3027 .

  • N.M. Todorović, M. Stefanović, B. Tinant, J.-P. Declercq, M.T. Makler, B.A. Šolaja , Steroids 61 (1996) 688–696.

    Šolaja B.A. , '' (1996 ) 61 Steroids : 688 -696 .

  • K.J. McCullough, J.K. Wood, A.K. Bhattacharjee, Y. Dong, D.E. Kyle, W.K. Milhous , and J.L. Vennerstrom , J. Med. Chem. 43 (2000) 1246–1249.

    Vennerstrom J.L. , '' (2000 ) 43 J. Med. Chem. : 1246 -1249 .

  • S. Tonmunphean, A. Wijitkosooma, Y. Tantirungrotechai , Bioorg. Med. Chem. 12 (2004) 2005–2012.

    Tantirungrotechai Y. , '' (2004 ) 12 Bioorg. Med. Chem. : 2005 -2012 .

  • R. Amewu, A.V. Stachulski, S.A. Ward, N.G. Berry, P.G. Bray, J. Davies, G. Labat, L. Vivas, P.M. O’Neill , Org. Biomol. Chem. 4 (2006) 4431–4436.

    O’Neill P.M. , '' (2006 ) 4 Org. Biomol. Chem. : 4431 -4436 .

  • N.C. Waters, G.S. Dow, M.P. Kozar , Exp. Opin. Therap. Pat. 14 (2004) 1125–1138 and references cited therein.

    Kozar M.P. , '' (2004 ) 14 Exp. Opin. Therap. Pat. : 1125 -1138 .

  • G.H. Posner, A.J. McRiner, I.-H. Paik, S. Sur, K. Borstnik, S. Xie, T.A. Shapiro, A. Alagbal, B. Foster , J. Med. Chem. 47(5) (2004) 1299–1301.

    Foster B. , '' (2004 ) 47 J. Med. Chem. : 1299 -1301 .

  • A.G. Griesbeck, T.T. El-Idreesy, L.-O. Höinck, J. Lex, R. Brun , Bioorg. Med. Chem. Lett. 15 (2005) 595–597.

    Brun R. , '' (2005 ) 15 Bioorg. Med. Chem. Lett. : 595 -597 .

  • C. Singh, U. Sharma, G. Saxena, S.K. Puri , Bioorg. Med. Chem. Lett. 17 (2007) 4097–4101.

    Puri S.K. , '' (2007 ) 17 Bioorg. Med. Chem. Lett. : 4097 -4101 .

  • M. Padmanilayam, B. Scorneaux, Y. Dong, J. Chollet, H. Matile, S.A. Charman, D.J. Creek, W.N. Charman, J.S. Tomas, C. Scheurer, S. Wittlin, R. Brun, J.L. Vennerstrom , Bioorg. Med. Chem. Lett. 16 (2006) 5542–5545.

    Vennerstrom J.L. , '' (2006 ) 16 Bioorg. Med. Chem. Lett. : 5542 -5545 .

  • Y. Dong, Y. Tang, J. Chollet, H. Matile, S. Wittlin, S.A. Charman, W.N. Charman, J.S. Tomas, C. Scheurer, C. Snyder, B. Scorneaux, S. Bajpai, S.A. Alexander, X. Wang, M. Padmanilayam, S.R. Cheruku, R. Brun, J.L. Vennerstrom , Bioorg. Med. Chem. 14 (2006) 6368–6382.

    Vennerstrom J.L. , '' (2006 ) 14 Bioorg. Med. Chem. : 6368 -6382 .

  • Y. Tang, Y. Dong, S. Wittlin, S.A. Charman, J. Chollet, F.C.K. Chiu, W.N. Charman, H. Matile, H. Urwyler, A. Dorn, S. Bajpai, X. Wang, M. Padmanilayam, J.M. Karle, R. Brun, L.V. Jonathan , Bioorg. Med. Chem. Lett. 17 (2007) 1260–1265.

    Jonathan L.V. , '' (2007 ) 17 Bioorg. Med. Chem. Lett. : 1260 -1265 .

  • K.J. McCullough, M. Nojima , Curr. Org. Chem. 5(6) (2001) 601–636.

    Nojima M. , '' (2001 ) 5 Curr. Org. Chem. : 601 -636 .

  • J. Li, Y.L. Wu , Curr. Med. Chem. 10(21) (2003) 2197–2230.

    Wu Y.L. , '' (2003 ) 10 Curr. Med. Chem. : 2197 -2230 .

  • D. Opsenica, G. Pocsfalvi, Z. Juranić, B. Tinant, J.-P. Declercq, D.E. Kyle, W.K. Milhous, B.A. Šolaja , J. Med. Chem. 43 (2000) 3274–3282.

    Šolaja B.A. , '' (2000 ) 43 J. Med. Chem. : 3274 -3282 .

  • B. Šolaja, N. Terzić, G. Pocsfalvi, L. Gerena, B. Tinant, D. Opsenica, W.K. Milhous , J. Med. Chem. 45 (2002) 3331–3336.

    Milhous W.K. , '' (2002 ) 45 J. Med. Chem. : 3331 -3336 .

  • I. Opsenica, N. Terzić, D. Opsenica, G. Angelovski, M. Lehnig, P. Eilbracht, B. Tinant, Z. Juranić, K.S. Smith, Y.S. Yang, D.S. Diaz, P.L. Smith, W.K. Milhous, D. Đoković, B.A. Šolaja , J. Med. Chem. 49 (2006) 3790–3799.

    Šolaja B.A. , '' (2006 ) 49 J. Med. Chem. : 3790 -3799 .

  • N. Terzić, D. Opsenica, D. Milić, B. Tinant, K.S. Smith, W.K. Milhous, B.A. Šolaja , J. Med. Chem. 50 (2007) 5118–5127.

    Šolaja B.A. , '' (2007 ) 50 J. Med. Chem. : 5118 -5127 .

  • D. Opsenica, G. Angelovski, G. Pocsfalvi, Z. Juranić, Ž. Žižak, D. Kyle, W.K. Milhous, B.A. Šolaja , Bioorg. Med. Chem. 11 (2003) 2761–2768.

    Šolaja B.A. , '' (2003 ) 11 Bioorg. Med. Chem. : 2761 -2768 .

  • S. Gaica, D. Opsenica, B. Šolaja, Ž. Tešić, D. Milojković-Opsenica , J. Planar Chromatogr. 15 (2002) 299–305.

    Milojković-Opsenica D. , '' (2002 ) 15 J. Planar Chromatogr. : 299 -305 .

  • S. Gaica, D. Opsenica, B. Šolaja, Ž. Tešić, D. Milojković-Opsenica , J. Planar Chromatogr. 17 (2004) 342–349.

    Milojković-Opsenica D. , '' (2004 ) 17 J. Planar Chromatogr. : 342 -349 .

  • M. Natić, R. Marković, D. Milojković-Opsenica, Ž. Tešić , J. Separ. Sci. 30 (2007) 2241–2248.

    Tešić , '' (2007 ) 30 J. Separ. Sci. : 2241 -2248 .

  • M. Stefaniak, A. Niestroj, J. Klupsch, J. Sliwiok, A. Pyka , Chromatographia 62 (2005) 87–89.

    Pyka A. , '' (2005 ) 62 Chromatographia : 87 -89 .

  • Z. Hussain , Chromatographia 63 (2006) 327–330.

    Hussain Z. , '' (2006 ) 63 Chromatographia : 327 -330 .

  • S.A. Mjos , J. Chromatogr. A 1100 (2005) 185–192.

    Mjos S.A. , '' (2005 ) 1100 J. Chromatogr. A : 185 -192 .

  • C. Colominas, J. Teixido, J. Cemell, F.J. Luque, M. Orozco , J. Phys. Chem. B 102 (1998) 2269–2276.

    Orozco M. , '' (1998 ) 102 J. Phys. Chem. B : 2269 -2276 .

  • A. Nasal, D. Siluk, R. Kaliszan , Curr. Med. Chem. 10 (2003) 381–426.

    Kaliszan R. , '' (2003 ) 10 Curr. Med. Chem. : 381 -426 .

  • H. Majstorović, D. Ratkov-Žebeljan, Ž.Lj. Tešić, D.M. Milojković-Opsenica , J. Planar Chromatogr. 17 (2004) 9–13.

    Milojković-Opsenica D.M. , '' (2004 ) 17 J. Planar Chromatogr. : 9 -13 .

  • W. Pru, Y. Vander Heyden, D.L. Massart, T. Kowalska , Acta Chrom. 8 (1998) 98–107.

    Kowalska T. , '' (1998 ) 8 Acta Chrom. : 98 -107 .

  • K. Saitoh, M. Kobayashi, N. Suzuki , Anal. Chem. 53 (1981) 2309–2313.

    Suzuki N. , '' (1981 ) 53 Anal. Chem. : 2309 -2313 .

  • Sz. Nyiredy , J. Chromatogr. B 812 (2004) 35–51.

    Nyiredy Sz. , '' (2004 ) 812 J. Chromatogr. B : 35 -51 .

  • B.K. Lavine, J.S. Ritter, S. Peterson , J. Chromatogr. A 946 (2002) 83–90.

    Peterson S. , '' (2002 ) 946 J. Chromatogr. A : 83 -90 .

  • Collapse
  • Expand

To see the editorial board, please visit the website of Springer Nature.

Manuscript Submission: HERE

For subscription options, please visit the website of Springer Nature.

Journal of Planar Chromatography - Modern TLC
Language English
Size A4
Year of
Foundation
1988
Volumes
per Year
1
Issues
per Year
6
Founder Akadémiai Kiadó
Founder's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 0933-4173 (Print)
ISSN 1789-0993 (Online)

Monthly Content Usage

Abstract Views Full Text Views PDF Downloads
Nov 2023 3 0 0
Dec 2023 16 1 0
Jan 2024 5 0 2
Feb 2024 1 2 0
Mar 2024 0 1 0
Apr 2024 4 0 0
May 2024 0 0 0