Possible antineoplastic agents, part XVI: Synthesis, In Vivo Antitumor and Invitro antiangiogenic study of few glutamic acid analogs

International Journal of Pharmaceutical Sciences Review and Research

Volumn 10, Issue 2, 2011, Pages 118-124

  Sen, Subrata ^a   Sarker, Koushik ^a   Ghosh, Avijit ^a   Mishra, Suvasish ^a   Saha, Abhijit ^a   Goswami, Diptendu ^b   Jha, Tarun ^b   Gupta, Jayanta Kumar ^b   De, Arun Uday ^a  

^a A P C Ray Memorial Cancer Chemotherapeutic Research Unit   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

EAC; Glutamic acid; HUVEC; Thalidomide; Vero

Indexed keywords

1 (3, 4 DIMETHOXYPHENYLSULFONYL) 5 OXO N PHENYLPYRROLIDINE 2 CARBOXAMIDE; 1 (3, 4 DIMETHOXYPHENYLSULFONYL) 5 OXOPYRROLIDINE 2 CARBOXYLIC ACID; 2 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) 5 OXO 5 (PHENYLAMINO) PENTANOIC ACID; 2 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) N1, N5 DIETHYLPENTANEDIAMIDE; 2 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) N1, N5 DIMETHYLPENTANEDIAMIDE; 2 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) N1, N5 DIPHENYLPENTANEDIAMIDE; 2 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) PENTANEDIAMIDE; 2 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) PENTANEDIOIC ACID; 2 (4 ETHOXY 3 METHOXYPHENYLSULFONAMIDO) 5 (BUTYLAMINO) 5 OXOPENTANOIC ACID; 2 (4 ETHOXY 3 METHOXYPHENYLSULFONAMIDO) 5 (ETHYLAMINO) 5 OXOPENTANOIC ACID; 4 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) 5 (METHYLAMINO) 5 OXOPENTANOIC ACID; 5 AMINO 4 (3, 4 DIMETHOXYPHENYLSULFONAMIDO) 5 OXOPENTANOIC ACID; DOXORUBICIN; GLUTAMIC ACID DERIVATIVE; MITOMYCIN C; N BUTYL 1 (3, 4 DIMETHOXYPHENYLSULFONYL) 5 OXOPYRROLIDINE 2 CARBOXAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ASSAY; CELL GROWTH; CELL LINE; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EHRLICH ASCITES TUMOR CELL; FEMALE; GROWTH INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; VERO CELL;

EID: 83255191753     PISSN: None     EISSN: 0976044X     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Graff S, Glutamic acid in malignant tumors, J. Biol. Chem. 13, 1939, 130.
2. Graff S, Rittenberg D, Foster G.L, The Glutamic acid of Malignant tumors, J. Biol. Chem. 133, 1940, 745.
3. th Edition, Mc Graw Hill, 2006, 302-304.
4. Eidinoff M.L, Knoll J.E, Marano B, Cheong L, Cancer Res. 18, 1958, 105.
5. Skeel Roland T, Hand book of cancer chemotherapy, 7th Edn, Lippincott, Williams & Wilkins, New York, 2008, p 157.
6. McPhee S. J, Papadakis M. A, Rabow M. W, Current Medical Diagnosis & treatment, Mac Graw Hill, 2011, p 505, 1398.
7. Bushby S.R.M, Schnitzer R.J, Hawking F, Experimental Chemotherapy, Academic Press Inc., Newyork, 1966, Vol 4, p 383-385.
8. Faigel J.W, Keberle H, Riess W, Schmid K, The metabolic fate of thalidomide, Experientia, 18, 1962, 389.
9. Leach B.E, Ford J.H, Whiffen A.J, Antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus, J.Am.Chem.Soc. 69, 1947, 474.
10. Field J.B, Mireless A, Pachl H.R, Bascoy L, Cano L, Bullock W.K, Experimental evaluation of a new antitumor agent, streptovitacin A. Antibiot.Ann, 6, 1959, 572.
11. Gatenbeck S, Sierankiewicz J, Microbial production of tenuazonic acid analogs, Antimicrob Agents Chemother, 3(2), 1973, 308.
12. Shigeura H.T, Gordon C.N, Biological activity of Tenuazonic acid, Biochemistry, 3(2), 1973, 1132.
13. Tso J.Y, Bower S. G, Zalkin H, Mechanism of Inactivation of Glutamine Amidotransferase by the Antitumor Drug L- (αS,5S)-a-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid (AT-125), Journal of Biological Chemistry, 255, 1980, 6734.
14. Catane R, Von Hoff DD, Glaubiger DL, Muggia FM, Azaserine, DON, and azotomycin: three diazo analogs of Lglutamine with clinical antitumor activity. Cancer Treat Rep., 63, 1979, 1033.
15. Moore J.A, Dice J.R, Nicholaides E.D, Westland R.D, Wittle E.L, Azaserine, synthetic studies. I, J.Am.Chem.Soc. 1954, 76, 2884.
16. Chen C. C, Zee-Cheng K. Y, Some antineoplastic antibiotics, J.Pharm.Sci., 61, 2006, 485.
17. Keren R, Stark A.A, Gamma-glutamyl transpeptidasedependent mutagenicity and cytotoxicity of gammaglutamyl derivatives: a model for biochemical targeting of chemotherapeutic agents, Environ. Mol. Mutagen. 32, 1998, 377.
18. Ingram V.M, Gene Mutations in Human Hæmoglobin: the Chemical Difference between Normal and Sickle Cell Hæmoglobin, Nature, 180, 1957, 326.
19. De A.U, Pal D, Possible Antineoplastic Agents I, J. Pharm. Sci., 64, 1975, 262.
20. De A.U, Pal D, Possible Antineoplastic Agents II, J. Pharm. Sci., 66, 1977, 232.
21. De A.U, Ghosh A.K, Possible Antineoplastic Agents: III Synthesis of 6-Alkyl-2-[4'-methoxyphthalimido] and 6-Alkyl-3-[3',4'-dimethoxyphenyl]glutarimides, J. Ind. Chem. Soc., 53, 1976, 1122
22. De A.U, Ghosh A.K, Possible Antineoplastic Agents: Part IVSynthesis & Antineoplastic Potency of N-Substituted α-(4,5- Dimethoxyphalimido)glutarimides & N-Substituted ß-(4- Bromophenyl)glutarimides, Ind. J. Chem., 16B, 1978, 510.
23. De A.U, Ghosh A.K, Possible Antineoplastic Agents: Part VSynthesis of 6-Alkyl-2- benzenesulphonamido-3- pheylglutarimides, Ind. J. Chem., 16B, 1978, 513.
24. De A.U, Bandyopadhya P, Hore A, Activity of N,N'-Dialkyl-2- (p-substituted benzenesulphonamido)glutarimides on Ehrlich Ascites Carcinoma (EAC), Ind. J. Chem., 19B, 1980, 920.
25. De A.U, Pandey J, Majumder (née Hore) A, Synthesis & Antineoplastic Activity of 5-N-Alkyl-2-p-substituted benzenesulphonyl-L-glutamines, Ind. J. Chem., 21B, 1982, 481.
26. De A.U, Majumder (née Hore) A, Jha T, Debnath A.K, Possible Antineoplastic Agents: Part VIII- Synthesis & Activity of 5-N-Substitued 3-p-substituted phenylglutaramic acids & 5-N-Substituted-2-benzenesulphonyl-3-phenyl-Lglutamines, Ind. J. Chem., 23B, 1984, 97.
27. De A.U, Jha T, Majumder A, Debnath A.K, Possible Antineoplastic Agents IX: Synthesis, Antineoplastic Activity and Quantitative Structure Activity Relationship of 5-NSubstituted-2-(chlorosubstituted benzenesulphonyl)-LGlutamines, Ind. J. Pharm. Sci., 47, 1985, 93.
28. Jha T, Debnath A.K, Majumder A, De A.U, Possible Antineoplastic Agents X: Synthesis, Antineoplastic Activity and QSAR Study of Some 5-N-Substituted-2- (chlorosubstituted benzenesulphonly)-L-glutamines and 5- N-Alkyl-2-(2',5'-dichlorobenzenesulphonyl)-L-glutamines, Ind. J. Pharm. Sci., 49, 1987, 133.
29. Jha T, Debnath A.K, Majumder A, De A.U, Possible Antineoplastic Agents: Part XI- QSAR, Analogs of Glutamines: Synthesis & Biological Activity of Some 5-NAlkyl-2-(substituted benzenesulphonyl)-L-glutamines, Ind. J. Chem., 26B,1987, 542.
30. Debnath A.K Jha T, Majumder A, De A.U, 4-(4'- Substitutedbenzoyl)aminobenzenesulphonyl-L-glutamines as potential antineoplastic agents: Synthesis, biological evaluation and QSAR studies, Ind. J. Chem., 28B, 1989, 843.
31. Purkayastha S.K, Jha T, Pal D.K, De A.U, Possible antineoplastic agents: Part XIII. Synthesis, biological evaluation and QSAR studies of some 1-(Substituted benzenesulphonyl)- 5-oxopyrrolidine-2-carboxylic acid derivatives, Anti-cancer Drug Des., 8, 1993, 95.
32. Purkayastha S.K, De A.U, Possible Antineoplastic Agents: Part 14 - Synthesis, Activity and QSAR Studies of Some 1- (Substituted Benzenesulphonyl)-5-ozopyrrolidine-2- carboxylic acid hydrazides, Bioorg.Med.Chem.Lett., 4, 1994, 377
33. Goswami D, Sen S, De A.U, Possible antineoplastic agents, Part-15: synthesis, biological activity and quantitative structure activity relationship of substituted-2-(4'- methoxybenzenesulphonamido)glutamic acid analogs against Ehrlich ascites carcinoma, Pharmazie, 5, 2001, 56.
34. Goswami D. Possible Antineoplastic Agents: Synthesis, Biological Evaluation QSAR Studies on Some Structural Variants of Glutamic Acid. Kolkata, India, Jadavpur University (2002) 75.