Home / Publications / Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship

Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship

Nikolay Alekseevich Zefirov 1, 2
Nikolay Alekseevich Zefirov
, 
Ann Kruth 3
Ann Kruth
, 
Birgit Wobith 3
Birgit Wobith
, 
Evgeniya Vladimirovna Nurieva 1
Evgeniya Vladimirovna Nurieva
, 
Syed Riyaz 4
Syed Riyaz
, 
Ch. Venkata Ramana Reddy 4
Ch. Venkata Ramana Reddy
, 
Sergei A Kuznetsov 3
Sergei A Kuznetsov
, 
Ol'ga Nikolaevna Zefirova 1, 2
Ol'ga Nikolaevna Zefirova
10.1016/j.mencom.2018.09.007
Published 2018-09-07
Communication , Volume 28, Issue 5, 475-478
7
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Zefirov N. A. et al. Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 475-478.
GOST all authors (up to 50) Copy
Zefirov N. A., Kruth A., Wobith B., Nurieva E. V., Riyaz S., Venkata Ramana Reddy C., Kuznetsov S. A., Zefirova O. N. Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 475-478.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.09.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.007
TI - Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship
T2 - Mendeleev Communications
AU - Zefirov, Nikolay Alekseevich
AU - Kruth, Ann
AU - Wobith, Birgit
AU - Nurieva, Evgeniya Vladimirovna
AU - Riyaz, Syed
AU - Venkata Ramana Reddy, Ch.
AU - Kuznetsov, Sergei A
AU - Zefirova, Ol'ga Nikolaevna
PY - 2018
DA - 2018/09/07
PB - Mendeleev Communications
SP - 475-478
IS - 5
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Zefirov,
author = {Nikolay Alekseevich Zefirov and Ann Kruth and Birgit Wobith and Evgeniya Vladimirovna Nurieva and Syed Riyaz and Ch. Venkata Ramana Reddy and Sergei A Kuznetsov and Ol'ga Nikolaevna Zefirova},
title = {Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.007},
number = {5},
pages = {475--478},
doi = {10.1016/j.mencom.2018.09.007}
}
MLA
Cite this
MLA Copy
Zefirov, Nikolay Alekseevich, et al. “Novel bridged and caged C4-podophyllotoxin derivatives as microtubule disruptors: synthesis, cytotoxic evaluation and structure–activity relationship.” Mendeleev Communications, vol. 28, no. 5, Sep. 2018, pp. 475-478. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.007.

Abstract

New podophyllotoxin C4-derivatives with bridged and cage moieties were synthesized by the Steglich esterification of podophyllotoxin with polycyclic carboxylic acids or by etherication with (adamantan-1-yl)methanol in the presence of BF3·Et2O with the following separation of diastereomers. Most of the target compounds inhibited the growth of human lung carcinoma A549 cells, induced apoptosis, stimulated shortening of microtubules or induced their unusual curling and involution. The activity depends on the slightest differences in the structures of alicyclic moieties and the type of the bond between podophyllotoxin and alicyclic group.

References

1.
Recent Advances in the Chemistry and Biology of Podophyllotoxins
Yu X., Che Z., Xu H.
Chemistry - A European Journal, 2017
2.
Recent Progress on C-4-Modified Podophyllotoxin Analogs as Potent Antitumor Agents
Liu Y., Tian J., Qian K., Zhao X., Morris-Natschke S.L., Yang L., Nan X., Tian X., Lee K.
Medicinal Research Reviews, 2014
3.
Podophyllotoxin derivatives: a patent review (2012 – 2014)
Kamal A., Ali Hussaini S.M., Rahim A., Riyaz S.
Expert Opinion on Therapeutic Patents, 2015
4.
Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins
López-Pérez J.L., del Olmo E., de Pascual-Teresa B., Abad A., San Feliciano A.
Bioorganic and Medicinal Chemistry Letters, 2004
5.
Synthesis and Antimitotic and Tubulin Interaction Profiles of Novel Pinacol Derivatives of Podophyllotoxins
Abad A., López-Pérez J.L., del Olmo E., García-Fernández L.F., Francesch A., Trigili C., Barasoain I., Andreu J.M., Díaz J.F., San Feliciano A.
Journal of Medicinal Chemistry, 2012
6.
Molecular Shape Diversity of Combinatorial Libraries:  A Prerequisite for Broad Bioactivity
Sauer W.H., Schwarz M.K.
Journal of Chemical Information and Computer Sciences, 2003
7.
GVK Biosciences Pvt. Ltd Proprietary Databases, https://www.gostardb.com.
8.
B.T. Yajie, X. Li, Patent CN 102875565, 2013.
9.
Zefirova O.N., Nurieva E.V., Lemcke H., Ivanov A.A., Zyk N.V., Weiss D.G., Kuznetsov S.A., Zefirov N.S.
Mendeleev Communications, 2008
10.
Synthesis of adamantane derivatives. XII. Schmidt reaction of adamantan-2-one
Sasaki T., Eguchi S., Toru T.
Journal of Organic Chemistry, 1970
11.
L. Tafesse, N. Tsuno, X. Zhou, Patent ES 2583146, 2016.
12.
Synthesis and Reactions of 3- and 3,7-Substituted Bicyclo[3.3.1]nonanes
Liu J., Gauger G., Kovacic P.
Journal of Organic Chemistry, 1973
13.
A convergent synthesis of alkyne–azide cycloaddition derivatives of 4-α,β-2-propyne podophyllotoxin depicting potent cytotoxic activity
Zilla M.K., Nayak D., Vishwakarma R.A., Sharma P.R., Goswami A., Ali A.
European Journal of Medicinal Chemistry, 2014
15.
Nurieva E.V., Zefirov N.A., Mamaeva A.V., Grishin Y.K., Kuznetsov S.A., Zefirova O.N.
Mendeleev Communications, 2017
16.
Vasilenko D.A., Averina E.B., Zefirov N.A., Wobith B., Grishin Y.K., Rybakov V.B., Zefirova O.N., Kuznetsova T.S., Kuznetsov S.A., Zefirov N.S.
Mendeleev Communications, 2017
17.
Synthesis and biological testing of (5Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones as antimitotic agents
Beloglazkina A.A., Wobith B., Barskaia E.S., Zefirov N.A., Majouga A.G., Beloglazkina E.K., Zyk N.V., Kuznetsov S.A., Zefirova O.N.
Medicinal Chemistry Research, 2016
18.
Unusual Tubulin-Clustering Ability of Specifically C7-Modified Colchicine Analogues
Zefirova O.N., Lemcke H., Lantow M., Nurieva E.V., Wobith B., Onishchenko G.E., Hoenen A., Griffiths G., Zefirov N.S., Kuznetsov S.A.
ChemBioChem, 2013
19.
Myosin Va Bound to Phagosomes Binds to F-Actin and Delays Microtubule-dependent Motility
Al-Haddad A., Shonn M.A., Redlich B., Blocker A., Burkhardt J.K., Yu H., Hammer J.A., Weiss D.G., Steffen W., Griffiths G., Kuznetsov S.A.
Molecular Biology of the Cell, 2001
20.
What is an apoptotic index measuring? A commentary
Potten C.
British Journal of Cancer, 1996
21.
Novel antimitotic agents related to tubuloclustin: synthesis and biological evaluation
Zefirova O.N., Nurieva E.V., Wobith B., Gogol V.V., Zefirov N.A., Ogonkov A.V., Shishov D.V., Zefirov N.S., Kuznetsov S.A.
Molecular Diversity, 2017
22.
Synthesis of steroid analogs of tubuloclustin, their cytotoxicity and effect on microtubules of A549 carcinoma cells
Nurieva E.V., Zefirov N.A., Mamaeva A.V., Wobith B., Kuznetsov S.A., Zefirova O.N.
Russian Chemical Bulletin, 2018