Synthesis and Antiproliferative Properties of Bifunctional Allocolchicine Derivatives

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

• 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