Synthesis and Antiproliferative Properties of Bifunctional Allocolchicine Derivatives

Iuliia A. Gracheva; Elena V. Svirshchevskaya; Vladimir I. Faerman; Irina P. Beletskaya; Alexey Yu. Fedorov

doi:10.1055/s-0037-1610146

Synthesis, Table of Contents

Synthesis 2018; 50(14): 2753-2760
DOI: 10.1055/s-0037-1610146

paper

Synthesis and Antiproliferative Properties of Bifunctional Allocolchicine Derivatives

Iuliia A. Gracheva

^aDepartment of Organic Chemistry, N.I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Avenue, 603950 Nizhny Novgorod, Russian Federation Email: afnn@rambler.ru

,

Elena V. Svirshchevskaya

^bLaboratory of Cell Interactions, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry RAS, 16/10 Miklukho-Maklaya Street, 117997 Moscow, Russian Federation

,

Vladimir I. Faerman

^aDepartment of Organic Chemistry, N.I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Avenue, 603950 Nizhny Novgorod, Russian Federation Email: afnn@rambler.ru

,

Irina P. Beletskaya

^cDepartment of Chemistry, M. V. Lomonosov Moscow State University, 1-3 Leninskiye Gory, 119992 Moscow, Russian Federation

,

Alexey Yu. Fedorov*

^aDepartment of Organic Chemistry, N.I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Avenue, 603950 Nizhny Novgorod, Russian Federation Email: afnn@rambler.ru

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Abstract

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Abstract

Based on the natural antimitotic agent colchifoline as a lead structure, a series of novel bifunctional allocolchicine congeners were synthesized from commercial colchicine. The new derivatives maintain good cytotoxicity against T₃M₄, MiaPaCa-2, and PANC-1 cell lines. The presence of functional groups simplifies further modifications of the prepared structures and the design of novel colchicine-derived antitumor compounds with desired pharmacological properties.

Key words

antitumor agents - colchicine - allocolchicine - tubulin - bifunctional derivatives

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References

References

1a Gewirtz DA. Bristol ML. Yalowich JC. Curr. Opin. Investig. Drugs 2010; 11: 612
1b Bae YH. Park K. J. Control. Release 2011; 153: 198

2 Ghosh S. Jha S. In Bioactive Molecules and Medicinal Plants . Ramawat KG. Mérillon JM. Springer-Verlag; Berlin: 2008: 215

3a Goldfinger SE. N. Engl. J. Med. 1972; 287: 1302
3b Graening T. Schmalz H.-G. Angew. Chem. Int. Ed. 2004; 43: 3230
3c Larsson S. Ronsted N. Curr. Top. Med. Chem. 2014; 14: 274

4a Jordan MA. Wilson L. Nat. Rev. Cancer 2004; 4: 253
4b Kumar A. Sharma PR. Mondhe DM. Anti-Cancer Drugs 2017; 28: 250

5a Sarı I. Birlik M. Kasifoğlu T. Eur. J. Rheum. 2014; 1: 21
5b Soskind R. Abazia DT. Bridgeman MB. Expert Opin. Pharmacother. 2017; 18: 1115

6a Cerquaglia C. Diaco M. Nucera G. Regina ML. Montalto M. Manna R. Curr. Drug Targets Inflamm. Allergy 2005; 4: 117
6b Gong Y. Gluud C. Am. J. Gastroenterol. 2005; 100: 1876
6c Saleh Z. Arayssi T. Ther. Adv. Chronic Dis. 2014; 5: 112
6d Morales A. Pari M. López-Lisbona R. Cubero N. Dorca J. Rosell A. Respiration 2016; 91: 251
6e Bibas R. Gaspar NK. Ramos-e-Silva M. J. Drugs Dermatol. 2005; 4: 196

7a Lennerz C. Barman M. Tantawy M. Sopher M. Whittaker P. Int. J. Cardiol. 2017; 249: 127
7b Imazio M. Brucato A. Adler Y. N. Engl. J. Med. 2014; 370: 781
7c Tong DC. Wilson AM. Layland J. Heart 2016; 102: 995
7d Verma S. Eikelboom JW. Nidorf SM. Al-Omran M. Gupta N. Teoh H. Friedrich JO. BMC Cardiovasc. Disord. 2015; 15: 96

8 Weiner JL. Buhler AV. Whatley VJ. Harris RA. Dunwiddie TV. J. Pharmacol. Exp. Ther. 1998; 284: 95

9a Holm JG. Ivyanskiy I. Thomsen SF. J. Dermatolog. Treat. 2017; 29: 80
9b Pereira EG. Guimarães TF. Bottino CB. D’Acri AM. Lima RB. Martins CJ. An. Bras. Dermatol. 2016; 91: 231
9c Zhang J. Rane G. Dai X. Shanmugam MK. Arfuso F. Samy RP. Lai MK. Kappei D. Kumar AP. Sethi G. Ageing Res. Rev. 2016; 25: 55

10a Shi Q. Chen K. Chen X. Brossi A. Verdier-Pinard P. Hamel E. McPhail AT. Tropsha A. Lee K.-H. J. Org. Chem. 1998; 63: 4018
10b Stockdill G. Dewar AE. N. Engl. J. Med. 1984; 310: 597

11 Bhattacharya S. Das A. Datta S. Ganguli A. Chakrabarti G. Tumour Biol. 2016; 37: 10653

12a Putterman C. Benchetrit E. Caraco Y. Levy M. Semin. Arthritis and Rheum. 1991; 21: 143
12b Dickinson M. Juneja S. Br. J. Haematol. 2009; 146: 465
12c Finkelstein Y. Aks SE. Hutson JR. Juurlink DN. Nguyen P. Dubnov-Raz G. Pollak U. Koren G. Bentur Y. Clin. Toxicol. 2010; 48: 407

13 Bockeria OL. Kanametov TN. Ann. Aritmologii. 2015; 12: 141

14a Yang Z. Wu W. Wang J. Liu L. Li L. Yang J. Wang G. Cao D. Zhang R. Tang M. Wen J. Zhu J. Xiang W. Wang F. Ma L. Xiang M. You J. Chen L. J. Med. Chem. 2014; 57: 7977
14b Jain V. Jain B. Tiwari P. Saini J. Jain UK. Pandey RS. Kumar M. Katare OP. Chandra R. Madan J. Anti-Cancer Drugs 2013; 4: 327

15a Svirshchevskaya EV. Gracheva IuA. Kuznetsov AG. Myrsikova EB. Grechikhina MV. Zubareva AA. Fedorov AYu. Med. Chem. (Los Angeles) 2016; 6: 571
15b Crielaard BJ. van der Wal S. Lammers T. Le HT. Hennink WE. Schiffelers RM. Storm G. Fens MH. Int. J. Nanomed. 2011; 6: 2697

16a Arias JL. Mini. Rev. Med. Chem. 2011; 11: 1
16b Thomas A. Teicher BA. Hassan R. Lancet Oncol. 2016; 17: 254
16c Bagnato JD. Eilers AL. Horton RA. Grissom CB. J. Org. Chem. 2004; 69: 8987
16d Kuznetsova NR. Svirshevskaya EB. Sitnikov NS. Abodo L. Sutorius H. Zapke J. Velder J. Tomopoulou P. Oschkinat H. Prokop A. Schmalz H.-G. Fedorov AYu. Vodovozova EL. Russ. J. Bioorg. Chem. 2013; 39: 543

17 Boyé O. Brossi A. In The Alkaloids: Chemistry and Pharmacology . Brossi A. Cordell GA. Academic Press; San Diego: 1992: 125

18a Sitnikov N. Velder J. Abodo L. Cuvelier N. Neudorfl J.-M. Prokop A. Krause G. Fedorov AYu. Schmalz H.-G. Chem. Eur. J. 2012; 18: 12096
18b Sitnikov NS. Kokisheva AS. Fukin GK. Neudorfl J.-M. Sutorius H. Prokop A. Fokin VV. Schmalz H.-G. Fedorov AYu. Eur. J. Org. Chem. 2014; 29: 6481
18c Sitnikov NS. Sintsov AV. Allegro D. Barbier P. Combes S. Onambele LA. Prokop A. Schmalz H.-G. Fedorov AYu. MedChemComm 2015; 6: 2158
18d Voitovich YuV. Shegravina ES. Sitnikov NS. Faerman VI. Fokin VV. Schmalz H.-G. Combes S. Allegro D. Barbier P. Beletskaya IP. Svirshchevskaya EV. Fedorov AYu. J. Med. Chem. 2015; 58: 692
18e Gracheva IuA. Voitovich IuV. Faerman VI. Sitnikov NS. Myrsikova EV. Schmalz H.-G. Svirshevskaya EV. Fedorov AYu. Eur. J. Med. Chem. 2017; 126: 432
18f Shchegravina ES. Maleev AA. Ignatov SK. Gracheva IuA. Stein A. Schmalz H.-G. Gavryushin AE. Zubareva AA. Svirshchevskaya EV. Fedorov AYu. Eur. J. Med. Chem. 2017; 141: 51
18g Shchegravina ES. Knyazev D. Svirshevskaya EV. Beletskaya IP. Schmalz H.-G. Fedorov AYu. Eur. J. Org. Chem. 2016; 34: 5620

19a Sugio K. Maruyama M. Tsurufuji S. Sharma PN. Brossi A. Life Sci. 1987; 40: 35
19b Sharma PN. Brossi A. Silverton JV. Chignell CF. J. Med. Chem. 1984; 27: 1729
19c Pırıldar S. Sütlüpinar N. Atasever B. Erdem-Kuruca S. Papouskova B. Šimánek V. Pharmaceut. Biol. 2010; 48: 32

20 Gracheva IuA. Svirshchevskaya EV. Zaburdaeva EA. Fedorov AYu. Synthesis 2017; 49: 4335
21 Nguyen TL. McGrath C. Hermone AR. Burnett JC. Zaharevitz DW. Day BW. Wipf P. Hamel E. Gussio R. J. Med. Chem. 2005; 48: 6107
22 Mosmann T. J. Immunol. Methods 1983; 65: 55

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