Synthesis of new phosphate derivative of benzothiazole and its inhibiting effect on two series of human neuroblastoma cell growth

Mahshid Nikpour Nezhati; Gholam Hossein Riazi; Homayon Ahmad Panahi; Elham Moniri; Nasir Ahmad Rajabi; Mohammad Mehdi Sadughi; Natasha Rahmani Zaker; Robab Ardekani; Reihaneh Kooshkestani

Korean Journal of Chemical Engineering, Vol.30, No.3, 675-679, March, 2013

DOI10.1007/s11814-012-0191-0 Export Citation

Synthesis of new phosphate derivative of benzothiazole and its inhibiting effect on two series of human neuroblastoma cell growth

Mahshid Nikpour Nezhati^{1, †}, Gholam Hossein Riazi², Homayon Ahmad Panahi¹, Elham Moniri³, Nasir Ahmad Rajabi^{4, 5}, Mohammad Mehdi Sadughi^{1, 6}, Natasha Rahmani Zaker⁷, Robab Ardekani⁸, and Reihaneh Kooshkestani¹

¹Department of Chemistry, Islamic Azad University, Central Tehran Branch, Tehran, Iran
²Department of Pharmacology, Tehran University, Tehran, Iran
³Department of Chemistry, Islamic Azad University, Varamin Branch (Pishva), Iran
⁴Department of Chemistry, Imam Khomeini International University (IKIU), Qazvine, Iran
⁵Young Researchers Club, Islamic Azad University, Central Tehran Branch, Tehran, Iran
⁶Young Researchers Club, Islamic Azad University, Ghaemshahr Branch, Tehran, Iran
⁷Department of Microbiology, Islamic Azad University, Science and Research Campus, Tehran, Iran
⁸Department of Biochemistry, Alzahra University, Tehran, Iran

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The sodium salt of di ((1-hydroxy-2-benzothiazolium-1-yl) ethyliden-1,1-H-bisphosphonic acid) orthophosphate was synthesized and its toxicity and viability effects screened on two different human neuroblastoma cell lines. This novel derivative of benzothiazole provides a new compound in connection with research and therapeutic application for tumor cell growth inhibition. Benzothiazole was alkylated in reaction with bromoacetic acid and then converted to its H-bisphosphonic acid derivative in presence of H3PO3/POCl3. The procedure led to formation of two molecules of corresponding H-bisphosphonic acid which attached together via a phosphate bridge. The investigated compound exhibits activities (IC50 value) ranging from 14-23 μM (corresponding to human neuroblastoma SK-BE (2) and SK-NM-C cells).

Keywords:Benzothiazole;Bromoacetic Acid;Neuroblastoma;Viability;SK-BE (2);SK-NM-C

[References]

Reszka AA, Rodan GA, Mini. Rev. Med. Chem., 4, 711 (2004)
Green JR, Oncologist,, 9(Suppl. 4), 9, 3 (2004)
Martin MB, Grimely JS, Lewis JC, Heath HT, Bailey BN, Kendrick H, Yardley V, Caldera A, Lira R, Urbina JA, Moreno SNJ, Docampo R, Croft SL, Oldfield E, J. Med. Chem., 44, 909 (2001)
Yardley V, Khan AA, Martin MB, Slifer TL, Araujo FG, Moreno SNJ, Docampo R, Croft SL, Oldfield E, Antimicrob.Agents Chemother., 46, 929 (2002)
Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimely JS, Van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E, J. Med.Chem., 45, 2904 (2002)
Sanders JM, Ghosh S, Chan JMW, Meints G, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E, J. Med. Chem., 47, 375 (2004)
Riebeling C, Forsea AM, Raisova M, Orfanos CE, Geilen CC, Br. J. Cancer., 87, 366 (2002)
Forsea AM, Muller C, Rieibeling C, Orfanos CE, Geilen CC, Br. J. Cancer., 91, 803 (2004)
Kitagawa Y, Hiraga T, Yura Y, Yoneda T, Oncol. Rep., 13, 211 (2005)
Chuah C, Barnes DJ, Kwok M, Corbin A, Deininger MWN, Druker BJ, Melo JV, Leukemia., 19, 1896 (2005)
Roelofs AJ, Thompson K, Gordon S, Rogers MJ, Clin Cancer Res., (Suppl. 20),, 12, 6222s (2006)
Kimmel DB, J. Dent Res., 86, 1022 (2007)
Luhe A, Kunkele KP, Haiker M, Schad K, Zihlmann C, Bauss F, Suter L, Pfister T, Toxicol. In Vitro., 22, 899 (2008)
Erez R, Ebner S, Attali B, Shbat D, Bioorganic & Medicinal Chemistry Letters., 18, 816 (2008)
Maris JM, Matthay KK, J. Clin. Oncol., 17, 2264 (1999)
Kiran YB, et al., European J. Med. Chem., 43, 885 (2008)
Dubois SG, Kalika Y, Lukens JN, J. Pediatr. Hematol. Oncol., 21, 181 (1999)
Sohare Y, Shimada H, Scadeng M, Pollack H, Yamada S, Ye W, Reynolds CP, DeClerck YA, Cancer Res., 63, 3026 (2003)
Widler L, Jaeggi KA, Glatt M, Muller K, Bachmann R, Bisping M, Born AR, Cortesi R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green JR, J. Med.Chem., 45, 3721 (2002)
Takeuchi M, Sakamoto S, Yoshida M, Abe T, Isomura Y, Chem. Pharm. Bull., 41, 688 (1993)
Takeuchi M, Sakamoto S, Kawamuki K, Kurihara H, Nakahara H, Isomura Y, Chem. Pharm.Bull., 46, 1703 (1998)
Lavielle G, Hautefaye P, Schaeffer C, Boutin JA, Cudennec CA, Pierre A, A. J. Med. Chem., 34, 1998 (1991)
Smith AB, Taylor CM, Bencovic SJ, Hirshmann R, Tetrahedron Lett., 35, 6853 (1994)
Turhanen P, Vepsalainen J, Beilstein J. Org. Chem., 4, 7 (2008)
Kiran YB, Devendranath Reddy C, Gunasekar D, Suresh Reddy C, Annette Leon, Luiz CA, Barbosa C, European J. Med. Chem., 43, 885 (2008)
Turhanen PA, Vepsalainen JJ, Synthesis., 13, 2119 (2005)
Turhanen PA, Ahlgren MJ, Jarvinen T, Vepsalainen JJ, Synthesis., 4, 633 (2001)

[1] Reszka AA, Rodan GA, Mini. Rev. Med. Chem., 4, 711 (2004)

[2] Green JR, Oncologist,, 9(Suppl. 4), 9, 3 (2004)

[3] Martin MB, Grimely JS, Lewis JC, Heath HT, Bailey BN, Kendrick H, Yardley V, Caldera A, Lira R, Urbina JA, Moreno SNJ, Docampo R, Croft SL, Oldfield E, J. Med. Chem., 44, 909 (2001)

[4] Yardley V, Khan AA, Martin MB, Slifer TL, Araujo FG, Moreno SNJ, Docampo R, Croft SL, Oldfield E, Antimicrob.Agents Chemother., 46, 929 (2002)

[5] Martin MB, Sanders JM, Kendrick H, de Luca-Fradley K, Lewis JC, Grimely JS, Van Brussel EM, Olsen JR, Meints GA, Burzynska A, Kafarski P, Croft SL, Oldfield E, J. Med.Chem., 45, 2904 (2002)

[6] Sanders JM, Ghosh S, Chan JMW, Meints G, Wang H, Raker AM, Song Y, Colantino A, Burzynska A, Kafarski P, Morita CT, Oldfield E, J. Med. Chem., 47, 375 (2004)

[7] Riebeling C, Forsea AM, Raisova M, Orfanos CE, Geilen CC, Br. J. Cancer., 87, 366 (2002)

[8] Forsea AM, Muller C, Rieibeling C, Orfanos CE, Geilen CC, Br. J. Cancer., 91, 803 (2004)

[9] Kitagawa Y, Hiraga T, Yura Y, Yoneda T, Oncol. Rep., 13, 211 (2005)

[10] Chuah C, Barnes DJ, Kwok M, Corbin A, Deininger MWN, Druker BJ, Melo JV, Leukemia., 19, 1896 (2005)

[11] Roelofs AJ, Thompson K, Gordon S, Rogers MJ, Clin Cancer Res., (Suppl. 20),, 12, 6222s (2006)

[12] Kimmel DB, J. Dent Res., 86, 1022 (2007)

[13] Luhe A, Kunkele KP, Haiker M, Schad K, Zihlmann C, Bauss F, Suter L, Pfister T, Toxicol. In Vitro., 22, 899 (2008)

[14] Erez R, Ebner S, Attali B, Shbat D, Bioorganic & Medicinal Chemistry Letters., 18, 816 (2008)

[15] Maris JM, Matthay KK, J. Clin. Oncol., 17, 2264 (1999)

[16] Kiran YB, et al., European J. Med. Chem., 43, 885 (2008)

[17] Dubois SG, Kalika Y, Lukens JN, J. Pediatr. Hematol. Oncol., 21, 181 (1999)

[18] Sohare Y, Shimada H, Scadeng M, Pollack H, Yamada S, Ye W, Reynolds CP, DeClerck YA, Cancer Res., 63, 3026 (2003)

[19] Widler L, Jaeggi KA, Glatt M, Muller K, Bachmann R, Bisping M, Born AR, Cortesi R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green JR, J. Med.Chem., 45, 3721 (2002)

[20] Takeuchi M, Sakamoto S, Yoshida M, Abe T, Isomura Y, Chem. Pharm. Bull., 41, 688 (1993)

[21] Takeuchi M, Sakamoto S, Kawamuki K, Kurihara H, Nakahara H, Isomura Y, Chem. Pharm.Bull., 46, 1703 (1998)

[22] Lavielle G, Hautefaye P, Schaeffer C, Boutin JA, Cudennec CA, Pierre A, A. J. Med. Chem., 34, 1998 (1991)

[23] Smith AB, Taylor CM, Bencovic SJ, Hirshmann R, Tetrahedron Lett., 35, 6853 (1994)

[24] Turhanen P, Vepsalainen J, Beilstein J. Org. Chem., 4, 7 (2008)

[25] Kiran YB, Devendranath Reddy C, Gunasekar D, Suresh Reddy C, Annette Leon, Luiz CA, Barbosa C, European J. Med. Chem., 43, 885 (2008)

[26] Turhanen PA, Vepsalainen JJ, Synthesis., 13, 2119 (2005)

[27] Turhanen PA, Ahlgren MJ, Jarvinen T, Vepsalainen JJ, Synthesis., 4, 633 (2001)