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Bioorganic and Medicinal Chemistry

Volumn 18, Issue 16, 2010, Pages 6080-6088

Dimethylaminopyridine derivatives of lupane triterpenoids are potent disruptors of mitochondrial structure and function

(6) Holy, Jon a Kolomitsyna, Oksana b Krasutsky, Dmytro b Oliveira, Paulo J c Perkins, Edward d Krasutsky, Pavel A b

a UNIVERSITY OF MINNESOTA MEDICAL SCHOOL (United States)

b UNIVERSITY OF MINNESOTA DULUTH (United States)

c UNIVERSITY OF COIMBRA (Portugal)

d MERCER UNIVERSITY SCHOOL OF MEDICINE (United States)

Author keywords

Cell proliferation; Dimethylaminopyridine; Lupane triterpenoid; Melanoma; Mitochondria

Indexed keywords

3BETA [2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY] 30 (4 DIMETHYLAMINOPYRIDINIO)LUP 20 EN 28 OIC ACID BROMIDE CHLORIDE; 3BETA [2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY] 30 (4 DIMETHYLAMINOPYRIDINIO)LUP 20 EN 28 OIC ACID DIBROMIDE; 3BETA [2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY]LUP 20 EN 28 OIC ACID BROMIDE; 3BETA [2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY]LUP 20 EN 28 OL BROMIDE; 3BETA [2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY]LUP 20 EN 28 OL CHLORIDE; 3BETA HYDROXY 28 [2 (4 DIMETHYLAMINOPYRIDINIO)PROPANYLOXY]LUP 20 EN 28 OL CHLORIDE; 3BETA HYDROXY 30 (4 DIMETHYLAMINOPYRIDINIO)LUP 20 EN 28 OIC ACID BROMIDE; 3BETA,28 DI[2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY] 30 (4 DIMETHYLAMINOPYRIDINIO)LUP 20 EN 29 BROMIDE DICHLORIDE; 3BETA,28 DI[2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY] 30 (4 DIMETHYLAMINOPYRIDINIO)LUP 20 EN TRIBROMIDE; 3BETA,28 DI[2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY]LUP 20 EN DIBROMIDE; 3BETA,28 DI[2 (4 DIMETHYLAMINOPYRIDINIO)ACETOXY]LUP 20 EN DICHLORIDE; 3BETA,28 DI[2 (4 DIMETHYLAMINOPYRIDINIO)BUTYRYLOXY]LUP 20 EN DIBROMIDE; 3BETA,28 DI[2 (4 DIMETHYLAMINOPYRIDINIO)PROPANYLOXY]LUP 20 EN DICHLORIDE; 3BETA,28 DI[3 (4 DIMETHYLAMINOPYRIDINIO)PROPIONYLOXY]LUP 20 EN DICHLORIDE; 3BETA,28 DI[4 (4 DIMETHYLAMINOPYRIDINIO)BUTYRYLOXY]LUP 20 EN DIBROMIDE; TRITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CELL FUNCTION; CELL GROWTH; CELL PROLIFERATION; CELL STRUCTURE; CELL TRANSFORMATION; CONTROLLED STUDY; DEPOLARIZATION; DRUG POTENCY; FIBROBLAST; FRAGMENTATION REACTION; HUMAN; HUMAN CELL; MITOCHONDRION; STRUCTURE ACTIVITY RELATION;

AMINOPYRIDINES; ANTINEOPLASTIC AGENTS; CELL LINE; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; MELANOMA; MITOCHONDRIA; MITOCHONDRIAL MEMBRANES; TRITERPENES;

EID: 77955472585 PISSN: 09680896 EISSN: None Source Type: Journal
DOI: 10.1016/j.bmc.2010.06.075 Document Type: Article

Times cited : (23)

References (44)

1
- 33751330871
- P. Krasutsky Nat. Prod. Rep. 23 2006 919
- (2006) Nat. Prod. Rep. , vol.23 , pp. 919
- Krasutsky, P.¹

2
- 73349109760
- A. Petronelli, G. Pannitteri, and U. Testa Anticancer Drugs 20 2009 880
- (2009) Anticancer Drugs , vol.20 , pp. 880
- Petronelli, A.¹ Pannitteri, G.² Testa, U.³

3
- 0028847024
- E. Pisha, H. Chai, I.S. Lee, T.E. Chagwedera, N.R. Farnsworth, G.A. Cordell, C.W. Beecher, H.H. Fong, A.D. Kinghorn, and D.M. Brown Nat. Med. 1 1995 1046
- (1995) Nat. Med. , vol.1 , pp. 1046
- Pisha, E.¹ Chai, H.² Lee, I.S.³ Chagwedera, T.E.⁴ Farnsworth, N.R.⁵ Cordell, G.A.⁶ Beecher, C.W.⁷ Fong, H.H.⁸ Kinghorn, A.D.⁹ Brown, D.M.¹⁰

4
- 0037049876
- V. Zuco, R. Supino, S.C. Righetti, L. Cleris, E. Marchesi, C. Gambacorti-Passerini, and F. Formelli Cancer Lett. 175 2002 17
- (2002) Cancer Lett. , vol.175 , pp. 17
- Zuco, V.¹ Supino, R.² Righetti, S.C.³ Cleris, L.⁴ Marchesi, E.⁵ Gambacorti-Passerini, C.⁶ Formelli, F.⁷

5
- 0032969291
- S. Fulda, I. Jeremias, H.H. Steiner, T. Pietsch, and K.M. Debatin Int. J. Cancer 82 1999 435
- (1999) Int. J. Cancer , vol.82 , pp. 435
- Fulda, S.¹ Jeremias, I.² Steiner, H.H.³ Pietsch, T.⁴ Debatin, K.M.⁵

6
- 0033023669
- W. Wick, C. Grimmel, B. Wagenknecht, J. Dichgans, and M. Weller J. Pharmacol. Exp. Ther. 289 1999 1306
- (1999) J. Pharmacol. Exp. Ther. , vol.289 , pp. 1306
- Wick, W.¹ Grimmel, C.² Wagenknecht, B.³ Dichgans, J.⁴ Weller, M.⁵

7
- 0030815250
- S. Fulda, C. Friesen, M. Los, C. Scaffidi, W. Mier, M. Benedict, G. Nunez, P.H. Krammer, M.E. Peter, and K.M. Debatin Cancer Res. 57 1997 4956
- (1997) Cancer Res. , vol.57 , pp. 4956
- Fulda, S.¹ Friesen, C.² Los, M.³ Scaffidi, C.⁴ Mier, W.⁵ Benedict, M.⁶ Nunez, G.⁷ Krammer, P.H.⁸ Peter, M.E.⁹ Debatin, K.M.¹⁰

8
- 0032189535
- S. Fulda, S.A. Susin, G. Kroemer, and K.M. Debatin Cancer Res. 58 1998 4453
- (1998) Cancer Res. , vol.58 , pp. 4453
- Fulda, S.¹ Susin, S.A.² Kroemer, G.³ Debatin, K.M.⁴

9
- 0033646961
- S. Fulda, and K.M. Debatin Med. Pediatr. Oncol. 35 2000 616
- (2000) Med. Pediatr. Oncol. , vol.35 , pp. 616
- Fulda, S.¹ Debatin, K.M.²

10
- 74049157757
- M.N. Laszczyk Planta Med. 75 2009 1549
- (2009) Planta Med. , vol.75 , pp. 1549
- Laszczyk, M.N.¹

11
- 34247526984
- K.T. Liby, M.M. Yore, and M.B. Sporn Nat. Rev. Cancer 7 2007 357
- (2007) Nat. Rev. Cancer , vol.7 , pp. 357
- Liby, K.T.¹ Yore, M.M.² Sporn, M.B.³

12
- 65549127616
- D. Deeb, X. Gao, H. Jiang, S.A. Dulchavsky, and S.C. Gautam Prostate 69 2009 851
- (2009) Prostate , vol.69 , pp. 851
- Deeb, D.¹ Gao, X.² Jiang, H.³ Dulchavsky, S.A.⁴ Gautam, S.C.⁵

13
- 68849092589
- I. Jutooru, G. Chadalapaka, S. Chintharlapalli, S. Papineni, and S. Safe Mol. Carcinog. 48 2009 692
- (2009) Mol. Carcinog. , vol.48 , pp. 692
- Jutooru, I.¹ Chadalapaka, G.² Chintharlapalli, S.³ Papineni, S.⁴ Safe, S.⁵

14
- 34548693457
- A.K. Pathak, M. Bhutani, A.S. Nair, K.S. Ahn, A. Chakraborty, H. Kadara, S. Guha, G. Sethi, and B.B. Aggarwal Mol. Cancer Res. 5 2007 943
- (2007) Mol. Cancer Res. , vol.5 , pp. 943
- Pathak, A.K.¹ Bhutani, M.² Nair, A.S.³ Ahn, K.S.⁴ Chakraborty, A.⁵ Kadara, H.⁶ Guha, S.⁷ Sethi, G.⁸ Aggarwal, B.B.⁹

15
- 67650995911
- N.H. Thoennissen, G.B. Iwanski, N.B. Doan, R. Okamoto, P. Lin, S. Abbassi, J.H. Song, D. Yin, M. Toh, W.D. Xie, J.W. Said, and H.P. Koeffler Cancer Res. 69 2009 5876
- (2009) Cancer Res. , vol.69 , pp. 5876
- Thoennissen, N.H.¹ Iwanski, G.B.² Doan, N.B.³ Okamoto, R.⁴ Lin, P.⁵ Abbassi, S.⁶ Song, J.H.⁷ Yin, D.⁸ Toh, M.⁹ Xie, W.D.¹⁰ Said, J.W.¹¹ Koeffler, H.P.¹²

16
- 35548996805
- Z.X. Xu, J. Liang, V. Haridas, A. Gaikwad, F.P. Connolly, G.B. Mills, and J.U. Gutterman Cell Death Differ. 14 2007 1948
- (2007) Cell Death Differ. , vol.14 , pp. 1948
- Xu, Z.X.¹ Liang, J.² Haridas, V.³ Gaikwad, A.⁴ Connolly, F.P.⁵ Mills, G.B.⁶ Gutterman, J.U.⁷

17
- 77955472774
- PCT/US2007/066896
- PCT/US2007/066896.

18
- 77955471120
- PCT/US2006/011794
- PCT/US2006/011794.

19
- 77955471080
- U.S. Patent 7410,958
- U.S. Patent 7410,958, 2008.
- (2008)

20
- 77955468764
- K. IV Nat. Prod. Commun. 2 2007
- (2007) Nat. Prod. Commun. , vol.2
- V, K.I.¹

21
- 0025341331
- P. Skehan, R. Storeng, D. Scudiero, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107
- (1990) J. Natl. Cancer Inst. , vol.82 , pp. 1107
- Skehan, P.¹ Storeng, R.² Scudiero, D.³ Monks, A.⁴ McMahon, J.⁵ Vistica, D.⁶ Warren, J.T.⁷ Bokesch, H.⁸ Kenney, S.⁹ Boyd, M.R.¹⁰

22
- 10744222249
- V.P. Skulachev, L.E. Bakeeva, B.V. Chernyak, L.V. Domnina, A.A. Minin, O.Y. Pletjushkina, V.B. Saprunova, I.V. Skulachev, V.G. Tsyplenkova, J.M. Vasiliev, L.S. Yaguzhinsky, and D.B. Zorov Mol. Cell Biochem. 256 and 257 2004 341
- (2004) Mol. Cell Biochem. , vol.256-257 , pp. 341
- Skulachev, V.P.¹ Bakeeva, L.E.² Chernyak, B.V.³ Domnina, L.V.⁴ Minin, A.A.⁵ Pletjushkina, O.Y.⁶ Saprunova, V.B.⁷ Skulachev, I.V.⁸ Tsyplenkova, V.G.⁹ Vasiliev, J.M.¹⁰ Yaguzhinsky, L.S.¹¹ Zorov, D.B.¹²

23
- 33745713089
- O.Y. Pletjushkina, K.G. Lyamzaev, E.N. Popova, O.K. Nepryakhina, O.Y. Ivanova, L.V. Domnina, B.V. Chernyak, and V.P. Skulachev Biochim. Biophys. Acta 1757 2006 518
- (2006) Biochim. Biophys. Acta , vol.1757 , pp. 518
- Pletjushkina, O.Y.¹ Lyamzaev, K.G.² Popova, E.N.³ Nepryakhina, O.K.⁴ Ivanova, O.Y.⁵ Domnina, L.V.⁶ Chernyak, B.V.⁷ Skulachev, V.P.⁸

24
- 0036906665
- F. Legros, A. Lombes, P. Frachon, and M. Rojo Mol. Biol. Cell 13 2002 4343
- (2002) Mol. Biol. Cell , vol.13 , pp. 4343
- Legros, F.¹ Lombes, A.² Frachon, P.³ Rojo, M.⁴

25
- 17144429793
- K.J. De Vos, V.J. Allan, A.J. Grierson, and M.P. Sheetz Curr. Biol. 15 2005 678
- (2005) Curr. Biol. , vol.15 , pp. 678
- De Vos, K.J.¹ Allan, V.J.² Grierson, A.J.³ Sheetz, M.P.⁴

26
- 57349160257
- G.M. Cereghetti, A. Stangherlin, O. Martins de Brito, C.R. Chang, C. Blackstone, P. Bernardi, and L. Scorrano Proc. Natl. Acad. Sci. U.S.A. 105 2008 15803
- (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 15803
- Cereghetti, G.M.¹ Stangherlin, A.² Martins De Brito, O.³ Chang, C.R.⁴ Blackstone, C.⁵ Bernardi, P.⁶ Scorrano, L.⁷

27
- 68149100711
- M. Wasilewski, and L. Scorrano Trends Endocrinol. Metab. 20 2009 287
- (2009) Trends Endocrinol. Metab. , vol.20 , pp. 287
- Wasilewski, M.¹ Scorrano, L.²

28
- 72749091027
- J.Y. Deng, S.J. Chen, G.M. Jow, C.W. Hsueh, and C.J. Jeng Chem. Res. Toxicol. 22 2009 1817
- (2009) Chem. Res. Toxicol. , vol.22 , pp. 1817
- Deng, J.Y.¹ Chen, S.J.² Jow, G.M.³ Hsueh, C.W.⁴ Jeng, C.J.⁵

29
- 46549085260
- Y. Zhang, X. Qi, L. Gong, Y. Li, L. Liu, X. Xue, Y. Xiao, X. Wu, and J. Ren Toxicology 249 2008 62
- (2008) Toxicology , vol.249 , pp. 62
- Zhang, Y.¹ Qi, X.² Gong, L.³ Li, Y.⁴ Liu, L.⁵ Xue, X.⁶ Xiao, Y.⁷ Wu, X.⁸ Ren, J.⁹

30
- 34648828532
- D.G. Hardie Nat. Rev. Mol. Cell Biol. 8 2007 774
- (2007) Nat. Rev. Mol. Cell Biol. , vol.8 , pp. 774
- Hardie, D.G.¹

31
- 64549087639
- J. Tian, S. Zhang, G. Li, Z. Liu, and B. Xu Phytother. Res. 23 2009 486
- (2009) Phytother. Res. , vol.23 , pp. 486
- Tian, J.¹ Zhang, S.² Li, G.³ Liu, Z.⁴ Xu, B.⁵

32
- 25144497185
- K. Anbarasi, G. Vani, and C.S. Devi J. Environ. Pathol. Toxicol. Oncol. 24 2005 225
- (2005) J. Environ. Pathol. Toxicol. Oncol. , vol.24 , pp. 225
- Anbarasi, K.¹ Vani, G.² Devi, C.S.³

33
- 0141507973
- H. Lapillonne, M. Konopleva, T. Tsao, D. Gold, T. McQueen, R.L. Sutherland, T. Madden, and M. Andreeff Cancer Res. 63 2003 5926
- (2003) Cancer Res. , vol.63 , pp. 5926
- Lapillonne, H.¹ Konopleva, M.² Tsao, T.³ Gold, D.⁴ McQueen, T.⁵ Sutherland, R.L.⁶ Madden, T.⁷ Andreeff, M.⁸

34
- 65449183737
- M.S. Lavhale, S. Kumar, S.H. Mishra, and S.L. Sitasawad PLoS One 4 2009 e5365
- (2009) PLoS One , vol.4 , pp. 5365
- Lavhale, M.S.¹ Kumar, S.² Mishra, S.H.³ Sitasawad, S.L.⁴

35
- 38549175872
- S. Papineni, S. Chintharlapalli, and S. Safe Mol. Pharmacol. 73 2008 553
- (2008) Mol. Pharmacol. , vol.73 , pp. 553
- Papineni, S.¹ Chintharlapalli, S.² Safe, S.³

36
- 33748627425
- M.K. Roy, M. Kobori, M. Takenaka, K. Nakahara, H. Shinmoto, and T. Tsushida Planta Med. 72 2006 917
- (2006) Planta Med. , vol.72 , pp. 917
- Roy, M.K.¹ Kobori, M.² Takenaka, M.³ Nakahara, K.⁴ Shinmoto, H.⁵ Tsushida, T.⁶

37
- 0032545386
- S. Fulda, C. Scaffidi, S.A. Susin, P.H. Krammer, G. Kroemer, M.E. Peter, and K.M. Debatin J. Biol. Chem. 273 1998 33942
- (1998) J. Biol. Chem. , vol.273 , pp. 33942
- Fulda, S.¹ Scaffidi, C.² Susin, S.A.³ Krammer, P.H.⁴ Kroemer, G.⁵ Peter, M.E.⁶ Debatin, K.M.⁷

38
- 69749094633
- S. Fulda, and G. Kroemer Drug Discovery Today 14 2009 885
- (2009) Drug Discovery Today , vol.14 , pp. 885
- Fulda, S.¹ Kroemer, G.²

39
- 0038492656
- Y. Tan, R. Yu, and J.M. Pezzuto Clin. Cancer Res. 9 2003 2866
- (2003) Clin. Cancer Res. , vol.9 , pp. 2866
- Tan, Y.¹ Yu, R.² Pezzuto, J.M.³

40
- 0037070178
- L. He, and J.J. Lemasters FEBS Lett. 512 2002 1
- (2002) FEBS Lett. , vol.512 , pp. 1
- He, L.¹ Lemasters, J.J.²

41
- 33847695241
- P.S. Brookes, K. Morse, D. Ray, A. Tompkins, S.M. Young, S. Hilchey, S. Salim, M. Konopleva, M. Andreeff, R. Phipps, and S.H. Bernstein Cancer Res. 67 2007 1793
- (2007) Cancer Res. , vol.67 , pp. 1793
- Brookes, P.S.¹ Morse, K.² Ray, D.³ Tompkins, A.⁴ Young, S.M.⁵ Hilchey, S.⁶ Salim, S.⁷ Konopleva, M.⁸ Andreeff, M.⁹ Phipps, R.¹⁰ Bernstein, S.H.¹¹

42
- 0003750420
- Springer Berlin
- V.P. Skulachev Membrane Bioenergetics 1988 Springer Berlin
- (1988) Membrane Bioenergetics
- Skulachev, V.P.¹

43
- 0030872907
- M.P. Murphy Trends Biotechnol. 15 1997 326
- (1997) Trends Biotechnol. , vol.15 , pp. 326
- Murphy, M.P.¹

44
- 0035797118
- J.S. Modica-Napolitano, and J.R. Aprille Adv Drug Delivery Rev. 49 2001 63
- (2001) Adv Drug Delivery Rev. , vol.49 , pp. 63
- Modica-Napolitano, J.S.¹ Aprille, J.R.²

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