Synthesis, Characterization and Anticancer Screening of Psammosilenin B: A Cyclic Octapeptide

Nirmala V. Shinde; Avinash S. Dhake; Kishan P. Haval

doi:10.14233/ajchem.2015.18612

Issue

Vol. 27 No. 3 (2015): Vol 27 Issue 3

Issue Published : January 19, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization and Anticancer Screening of Psammosilenin B: A Cyclic Octapeptide

https://doi.org/10.14233/ajchem.2015.18612

Nirmala V. Shinde

Department of Pharmaceutical Sciences, Jawaharlal Nehru Technological University, Kakinada-533 003, India; Department of Pharmaceutical Chemistry, S.M.B.T. College of Pharmacy, Nandi Hills, Dhamangaon-422 403, India

Avinash S. Dhake

Department of Pharmaceutical Chemistry, S.M.B.T. College of Pharmacy, Nandi Hills, Dhamangaon-422 403, India

Kishan P. Haval

Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Sub Centre, Osmanabad-413 501, India

Corresponding Author(s) : Nirmala V. Shinde

nirmalampharm@rediffmail.com

Asian Journal of Chemistry, Vol. 27 No. 3 (2015): Vol 27 Issue 3
Article Published : January 18, 2015

Abstract

Synthesis and anticancer screening of cyclic octapeptide, Psammosilenin B is described. The structure of synthesized compound was confirmed by spectral analysis including FTIR, ¹H NMR, ¹³C NMR, MS and elemental analysis. From the results of screening against 60 human tumour cell lines, it was concluded that the newly synthesized cyclopeptide possessed prominant anticancer activity against HOP-92 cell lines of non small cell lung cancer, PC3 cell lines of prostate cancer and significant activity against HL-60(TB) cell lines of leukemia cancer in comparision with DTP One Dose Mean Graph of vincristine.

Keywords

Cyclic peptide Anticancer p-Nitrophenyl ester method Solution phase synthesis

V. Shinde, N., S. Dhake, A., & P. Haval, K. (2015). Synthesis, Characterization and Anticancer Screening of Psammosilenin B: A Cyclic Octapeptide. Asian Journal of Chemistry, 27(3), 1153–1156. https://doi.org/10.14233/ajchem.2015.18612

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References

H. Yoshioka, T. Aoki, H. Goko, K. Nakatsu, T. Noda, H. Sakakibara, T. Take, A. Nagata, J. Abe, T. Wakamiya, T. Shiba and T. Kaneko, Tetrahedron Lett., 12, 2043 (1971); doi:10.1016/S0040-4039(01)96775-9.
S.B.H. Kent, Annu. Rev. Biochem., 57, 957 (1988); doi:10.1146/annurev.bi.57.070188.004521.
T. Imaeda, Y. Hamada and T. Shioiri, Tetrahedron, 35, 591 (1994); doi:10.1016/S0040-4039(00)75846-1.
H. Morita, N. Yoshida, K. Takeya, H. Itokawa and O. Shirota, Tetrahedron, 52, 2795 (1996); doi:10.1016/0040-4020(95)01094-7.
R. Fernández, S. Omar, M. Feliz, E. Quinoá and R. Riguera, Tetrahedron Lett., 30, 6017 (1992); doi:10.1016/S0040-4039(00)61115-2.
J. Schimana, K. Gebhardt, A. Höltzel, D.G. Schmid, R. Süssmuth, J. Müller, R. Pukall and H.-P. Fiedler, J. Antibiot., 55, 565 (2002); doi:10.7164/antibiotics.55.565.
L. Bourel-Bonnet, K.V. Rao, M.T. Hamann and A. Ganesan, J. Med. Chem., 48, 1330 (2005); doi:10.1021/jm049841x.
M.A. Fara, J.J. Di’az-Mochon and M. Bradley, Tetrahedron Lett., 47, 1011 (2006); doi:10.1016/j.tetlet.2005.11.127.
S.H. Joo, Biomol. Ther., 20, 19 (2012); doi:10.4062/biomolther.2012.20.1.019.
N.V. Shinde, M. Himaja, S.K. Bhosale and R.D. Wagh, Asian J. Chem., 22, 996 (2010).
R. Dahiya and H. Gautam, Bull. Pharm. Res., 1, 1 (2011).
S. Chaudhary, H. Kumar, H. Verma and A. Rajpoot, Int. J. Pharm. Tech. Res., 4, 194 (2012).
J. Zhong and Y. Chau, Mol. Cancer Ther., 7, 2933 (2008); doi:10.1158/1535-7163.MCT-08-0528.
A.G. Shilabin, N. Kasanah, D.E. Wedge and M.T. Hamann, J. Med. Chem., 50, 4340 (2007); doi:10.1021/jm061288r.
Z.T. Ding and Y.C. Wang, Chin. Chem. Lett., 10, 1037 (1999).
M. Bodanszky and A. Bodanszky, Practice of Peptide Synthesis, Springer-Verlag, New York, p. 78 (1984).
NCI-60 DTP Human Tumor Cell Line Screen; http://dtp.nci.nih.gov/branches/btb/ivclsp.html.

References

H. Yoshioka, T. Aoki, H. Goko, K. Nakatsu, T. Noda, H. Sakakibara, T. Take, A. Nagata, J. Abe, T. Wakamiya, T. Shiba and T. Kaneko, Tetrahedron Lett., 12, 2043 (1971); doi:10.1016/S0040-4039(01)96775-9.

S.B.H. Kent, Annu. Rev. Biochem., 57, 957 (1988); doi:10.1146/annurev.bi.57.070188.004521.

T. Imaeda, Y. Hamada and T. Shioiri, Tetrahedron, 35, 591 (1994); doi:10.1016/S0040-4039(00)75846-1.

H. Morita, N. Yoshida, K. Takeya, H. Itokawa and O. Shirota, Tetrahedron, 52, 2795 (1996); doi:10.1016/0040-4020(95)01094-7.

R. Fernández, S. Omar, M. Feliz, E. Quinoá and R. Riguera, Tetrahedron Lett., 30, 6017 (1992); doi:10.1016/S0040-4039(00)61115-2.

J. Schimana, K. Gebhardt, A. Höltzel, D.G. Schmid, R. Süssmuth, J. Müller, R. Pukall and H.-P. Fiedler, J. Antibiot., 55, 565 (2002); doi:10.7164/antibiotics.55.565.

L. Bourel-Bonnet, K.V. Rao, M.T. Hamann and A. Ganesan, J. Med. Chem., 48, 1330 (2005); doi:10.1021/jm049841x.

M.A. Fara, J.J. Di’az-Mochon and M. Bradley, Tetrahedron Lett., 47, 1011 (2006); doi:10.1016/j.tetlet.2005.11.127.

S.H. Joo, Biomol. Ther., 20, 19 (2012); doi:10.4062/biomolther.2012.20.1.019.

N.V. Shinde, M. Himaja, S.K. Bhosale and R.D. Wagh, Asian J. Chem., 22, 996 (2010).

R. Dahiya and H. Gautam, Bull. Pharm. Res., 1, 1 (2011).

S. Chaudhary, H. Kumar, H. Verma and A. Rajpoot, Int. J. Pharm. Tech. Res., 4, 194 (2012).

J. Zhong and Y. Chau, Mol. Cancer Ther., 7, 2933 (2008); doi:10.1158/1535-7163.MCT-08-0528.

A.G. Shilabin, N. Kasanah, D.E. Wedge and M.T. Hamann, J. Med. Chem., 50, 4340 (2007); doi:10.1021/jm061288r.

Z.T. Ding and Y.C. Wang, Chin. Chem. Lett., 10, 1037 (1999).

M. Bodanszky and A. Bodanszky, Practice of Peptide Synthesis, Springer-Verlag, New York, p. 78 (1984).

NCI-60 DTP Human Tumor Cell Line Screen; http://dtp.nci.nih.gov/branches/btb/ivclsp.html.

Issue

Vol. 27 No. 3 (2015): Vol 27 Issue 3

Synthesis, Characterization and Anticancer Screening of Psammosilenin B: A Cyclic Octapeptide

Corresponding Author(s) : Nirmala V. Shinde

Abstract

Keywords

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