SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 50, Issue 42, 2011, Pages 9871-9874

Development of highly cytotoxic and actin-depolymerizing biotin derivatives of aplyronine A

(4) Kita, Masaki a Hirayama, Yuichiro a Sugiyama, Miyuki a Kigoshi, Hideo a

a UNIVERSITY OF TSUKUBA (Japan)

Author keywords

actin depolymerization; antitumor agents; chemical probes; natural products; proteins

Indexed keywords

ANTI-TUMOR AGENTS; CHEMICAL PROBES; CYTOTOXIC; MACROLIDES; MOLECULAR PROBES; NATURAL PRODUCTS; TUMOR CELLS;

COENZYMES; CYTOTOXICITY; DRUG PRODUCTS; ETHYLENE; GLYCOLS; POLYETHYLENE GLYCOLS; PROBES;

PROTEINS;

ACTIN; APLYRONINE A; BIOTIN; MACROLIDE;

ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECT; HELA CELL; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACTINS; BIOTIN; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HUMANS; MACROLIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80053900166 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201103802 Document Type: Article

Times cited : (36)

References (47)

1
- 0027763552
- For the isolation and structures of aplyronines, see: K. Yamada, M. Ojika, T. Ishigaki, Y. Yoshida, H. Ekimoto, M. Arakawa, J. Am. Chem. Soc. 1993, 115, 11020
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11020
- Yamada, K.¹ Ojika, M.² Ishigaki, T.³ Yoshida, Y.⁴ Ekimoto, H.⁵ Arakawa, M.⁶

2
- 0027981566
- M. Ojika, H. Kigoshi, T. Ishigaki, I. Tsukada, T. Tsuboi, T. Ogawa, K. Yamada, J. Am. Chem. Soc. 1994, 116, 7441
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7441
- Ojika, M.¹ Kigoshi, H.² Ishigaki, T.³ Tsukada, I.⁴ Tsuboi, T.⁵ Ogawa, T.⁶ Yamada, K.⁷

3
- 0029066587
- K. Suenaga, T. Ishigaki, A. Sakakura, H. Kigoshi, K. Yamada, Tetrahedron Lett. 1995, 36, 5053
- (1995) Tetrahedron Lett. , vol.36 , pp. 5053
- Suenaga, K.¹ Ishigaki, T.² Sakakura, A.³ Kigoshi, H.⁴ Yamada, K.⁵

4
- 0027716491
- M. Ojika, H. Kigoshi, T. Ishigaki, K. Yamada, Tetrahedron Lett. 1993, 34, 8501
- (1993) Tetrahedron Lett. , vol.34 , pp. 8501
- Ojika, M.¹ Kigoshi, H.² Ishigaki, T.³ Yamada, K.⁴

5
- 0027729914
- for the synthesis of aplyronines, see
- M. Ojika, H. Kigoshi, T. Ishigaki, M. Nishiwaki, I. Tsukada, K. Mizuta, K. Yamada, Tetrahedron Lett. 1993, 34, 8505; for the synthesis of aplyronines, see
- (1993) Tetrahedron Lett. , vol.34 , pp. 8505
- Ojika, M.¹ Kigoshi, H.² Ishigaki, T.³ Nishiwaki, M.⁴ Tsukada, I.⁵ Mizuta, K.⁶ Yamada, K.⁷

6
- 0028133332
- H. Kigoshi, M. Ojika, T. Ishigaki, K. Suenaga, T. Mutou, A. Sakakura, T. Ogawa, K. Yamada, J. Am. Chem. Soc. 1994, 116, 7443
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 7443
- Kigoshi, H.¹ Ojika, M.² Ishigaki, T.³ Suenaga, K.⁴ Mutou, T.⁵ Sakakura, A.⁶ Ogawa, T.⁷ Yamada, K.⁸

7
- 0028294579
- H. Kigoshi, M. Ojika, K. Suenaga, T. Mutou, J. Hirano, A. Sakakura, T. Ogawa, M. Nisiwaki, K. Yamada, Tetrahedron Lett. 1994, 35, 1247
- (1994) Tetrahedron Lett. , vol.35 , pp. 1247
- Kigoshi, H.¹ Ojika, M.² Suenaga, K.³ Mutou, T.⁴ Hirano, J.⁵ Sakakura, A.⁶ Ogawa, T.⁷ Nisiwaki, M.⁸ Yamada, K.⁹

8
- 16044370146
- H. Kigoshi, K. Suenaga, T. Mutou, T. Ishigaki, T. Atsumi, H. Ishiwata, A. Sakakura, T. Ogawa, M. Ojika, K. Yamada, J. Org. Chem. 1996, 61, 5326
- (1996) J. Org. Chem. , vol.61 , pp. 5326
- Kigoshi, H.¹ Suenaga, K.² Mutou, T.³ Ishigaki, T.⁴ Atsumi, T.⁵ Ishiwata, H.⁶ Sakakura, A.⁷ Ogawa, T.⁸ Ojika, M.⁹ Yamada, K.¹⁰

9
- 33847681881
- M. Ojika, H. Kigoshi, Y. Yoshida, T. Ishigaki, M. Nishiwaki, I. Tsukada, M. Arakawa, H. Ekimoto, K. Yamada, Tetrahedron 2007, 63, 3138.
- (2007) Tetrahedron , vol.63 , pp. 3138
- Ojika, M.¹ Kigoshi, H.² Yoshida, Y.³ Ishigaki, T.⁴ Nishiwaki, M.⁵ Tsukada, I.⁶ Arakawa, M.⁷ Ekimoto, H.⁸ Yamada, K.⁹

10
- 58149098544
- For reviews, see: K. Yamada, M. Ojika, H. Kigoshi, K. Suenaga, Nat. Prod. Rep. 2009, 26, 27
- (2009) Nat. Prod. Rep. , vol.26 , pp. 27
- Yamada, K.¹ Ojika, M.² Kigoshi, H.³ Suenaga, K.⁴

11
- 77955101485
- K. Yamada, M. Ojika, H. Kigoshi, K. Suenaga, Proc. Jpn. Acad. Ser. B 2010, 86, 176
- (2010) Proc. Jpn. Acad. Ser. B , vol.86 , pp. 176
- Yamada, K.¹ Ojika, M.² Kigoshi, H.³ Suenaga, K.⁴

12
- 33847789061
- (in Japanese).
- K. Suenaga, H. Kigoshi, J. Synth. Org. Chem. Jpn. 2006, 64, 1273 (in Japanese).
- (2006) J. Synth. Org. Chem. Jpn. , vol.64 , pp. 1273
- Suenaga, K.¹ Kigoshi, H.²

13
- 0029742550
- S. Saito, S. Watabe, H. Ozaki, H. Kigoshi, K. Yamada, N. Fusetani, H. Karaki, J. Biochem. (Tokyo) 1996, 120, 552.
- (1996) J. Biochem. (Tokyo) , vol.120 , pp. 552
- Saito, S.¹ Watabe, S.² Ozaki, H.³ Kigoshi, H.⁴ Yamada, K.⁵ Fusetani, N.⁶ Karaki, H.⁷

14
- 33749059234
- For general reviews on actin-depolymerizing natural products, see: J. S. Allingham, V. A. Klenchin, I. Rayment, Cell. Mol. Life Sci. 2006, 63, 2119
- (2006) Cell. Mol. Life Sci. , vol.63 , pp. 2119
- Allingham, J.S.¹ Klenchin, V.A.² Rayment, I.³

15
- 0344008063
- K. S. Yeung, I. Paterson, Angew. Chem. 2002, 114, 4826
- (2002) Angew. Chem. , vol.114 , pp. 4826
- Yeung, K.S.¹ Paterson, I.²

16
- 0037122039
- references therein.
- Angew. Chem. Int. Ed. 2002, 41, 4632, and references therein.
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4632

17
- 33847244843
- E. Vincent, J. Saxton, C. Baker-Glenn, I. Moal, J. D. Hirst, G. Pattenden, P. E. Shaw, Cell. Mol. Life Sci. 2007, 64, 487.
- (2007) Cell. Mol. Life Sci. , vol.64 , pp. 487
- Vincent, E.¹ Saxton, J.² Baker-Glenn, C.³ Moal, I.⁴ Hirst, J.D.⁵ Pattenden, G.⁶ Shaw, P.E.⁷

18
- 0027159833
- M. Hori, S. Saito, Y. Z. Shin, H. Ozaki, N. Fusetani, H. Karaki, FEBS Lett. 1993, 322, 151
- (1993) FEBS Lett. , vol.322 , pp. 151
- Hori, M.¹ Saito, S.² Shin, Y.Z.³ Ozaki, H.⁴ Fusetani, N.⁵ Karaki, H.⁶

19
- 0028062120
- S. Saito, S. Watabe, H. Ozaki, N. Fusetani, H. Karaki, J. Biol. Chem. 1994, 269, 29710
- (1994) J. Biol. Chem. , vol.269 , pp. 29710
- Saito, S.¹ Watabe, S.² Ozaki, H.³ Fusetani, N.⁴ Karaki, H.⁵

20
- 0031979334
- S. Wada, S. Matsunaga, S. Saito, N. Fusetani, S. Watabe, J. Biochem. 1998, 123, 946.
- (1998) J. Biochem. , vol.123 , pp. 946
- Wada, S.¹ Matsunaga, S.² Saito, S.³ Fusetani, N.⁴ Watabe, S.⁵

21
- 0344270893
- J. Tanaka, Y. Yan, J. Choi, J. Bai, V. A. Klenchin, I. Rayment, Proc. Natl. Acad. Sci. USA 2003, 100, 13851
- (2003) Proc. Natl. Acad. Sci. USA , vol.100 , pp. 13851
- Tanaka, J.¹ Yan, Y.² Choi, J.³ Bai, J.⁴ Klenchin, V.A.⁵ Rayment, I.⁶

22
- 27944486587
- C. Petchprayoon, K. Suwanborirux, J. Tanaka, Y. Yan, T. Sakata, G. Marriott, Bioconjugate Chem. 2005, 16, 1382.
- (2005) Bioconjugate Chem. , vol.16 , pp. 1382
- Petchprayoon, C.¹ Suwanborirux, K.² Tanaka, J.³ Yan, Y.⁴ Sakata, T.⁵ Marriott, G.⁶

23
- 0030777109
- X. Zhang, L. Minale, A. Zampella, C. D. Smith, Cancer Res. 1997, 57, 3751
- (1997) Cancer Res. , vol.57 , pp. 3751
- Zhang, X.¹ Minale, L.² Zampella, A.³ Smith, C.D.⁴

24
- 40749111496
- R. D. Perrins, G. Cecere, I. Paterson, G. Marriott, Chem. Biol. 2008, 15, 287.
- (2008) Chem. Biol. , vol.15 , pp. 287
- Perrins, R.D.¹ Cecere, G.² Paterson, I.³ Marriott, G.⁴

25
- 0028967310
- M. R. Bubb, I. Spector, A. D. Bershadsky, E. D. Korn, J. Biol. Chem. 1995, 270, 3463
- (1995) J. Biol. Chem. , vol.270 , pp. 3463
- Bubb, M.R.¹ Spector, I.² Bershadsky, A.D.³ Korn, E.D.⁴

26
- 0031980743
- S. Saito, S. Watabe, H. Ozaki, M. Jobayashi, T. Suzuki, H. Kobayashi, N. Fusetani, H. Karaki, J. Biochem. (Tokyo) 1998, 123, 571.
- (1998) J. Biochem. (Tokyo) , vol.123 , pp. 571
- Saito, S.¹ Watabe, S.² Ozaki, H.³ Jobayashi, M.⁴ Suzuki, T.⁵ Kobayashi, H.⁶ Fusetani, N.⁷ Karaki, H.⁸

27
- 33644806057
- A. V. Statsuk, R. Bai, J. L. Baryza, V. A. Verma, E. Hamel, P. A. Wender, S. A. Kozmin, Nat. Chem. Biol. 2005, 1, 383
- (2005) Nat. Chem. Biol. , vol.1 , pp. 383
- Statsuk, A.V.¹ Bai, R.² Baryza, J.L.³ Verma, V.A.⁴ Hamel, E.⁵ Wender, P.A.⁶ Kozmin, S.A.⁷

28
- 41949108288
- S. A. Rizvi, D. S. Courson, V. A. Keller, R. S. Rock, S. A. Kozmin, Proc. Natl. Acad. Sci. USA 2008, 105, 4088
- (2008) Proc. Natl. Acad. Sci. USA , vol.105 , pp. 4088
- Rizvi, S.A.¹ Courson, D.S.² Keller, V.A.³ Rock, R.S.⁴ Kozmin, S.A.⁵

29
- 77952872240
- S. A. Rizvi, S. Liu, Z. L. Chen, C. Skau, M. Pytynia, D. R. Kovar, S. J. Chmura, S. A. Kozmin, J. Am. Chem. Soc. 2010, 132, 7288.
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 7288
- Rizvi, S.A.¹ Liu, S.² Chen, Z.L.³ Skau, C.⁴ Pytynia, M.⁵ Kovar, D.R.⁶ Chmura, S.J.⁷ Kozmin, S.A.⁸

30
- 0038348755
- For reviews on small molecules that affect actin dynamics and the cytoskeleton, see: G. Fenteany, S. Zhu, Curr. Top. Med. Chem. 2003, 3, 593
- (2003) Curr. Top. Med. Chem. , vol.3 , pp. 593
- Fenteany, G.¹ Zhu, S.²

31
- 0036909567
- J. R. Peterson, T. J. Mitchison, Chem. Biol. 2002, 9, 1275.
- (2002) Chem. Biol. , vol.9 , pp. 1275
- Peterson, J.R.¹ Mitchison, T.J.²

32
- 0032829103
- For reviews on cancer chemotheraphy, see: I. Spector, F. Braet, N. R. Shochet, M. R. Bubb, Microsc. Res. Tech. 1999, 47, 18
- (1999) Microsc. Res. Tech. , vol.47 , pp. 18
- Spector, I.¹ Braet, F.² Shochet, N.R.³ Bubb, M.R.⁴

33
- 0642286487
- A. Giganti, E. Friederich, Prog. Cell Cycle Res. 2003, 5, 511.
- (2003) Prog. Cell Cycle Res. , vol.5 , pp. 511
- Giganti, A.¹ Friederich, E.²

34
- 0031552092
- K. Suenaga, N. Kamei, Y. Okugawa, M. Takagi, A. Akao, H. Kigoshi, K. Yamada, Bioorg. Med. Chem. Lett. 1997, 7, 269
- (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 269
- Suenaga, K.¹ Kamei, N.² Okugawa, Y.³ Takagi, M.⁴ Akao, A.⁵ Kigoshi, H.⁶ Yamada, K.⁷

35
- 0037016922
- H. Kigoshi, K. Suenaga, M. Takagi, A. Akao, K. Kanematsu, N. Kamei, Y. Okugawa, K. Yamada, Tetrahedron 2002, 58, 1075.
- (2002) Tetrahedron , vol.58 , pp. 1075
- Kigoshi, H.¹ Suenaga, K.² Takagi, M.³ Akao, A.⁴ Kanematsu, K.⁵ Kamei, N.⁶ Okugawa, Y.⁷ Yamada, K.⁸

36
- 33645473657
- T. Kuroda, K. Suenaga, A. Sakakura, T. Handa, K. Okamoto, H. Kigoshi, Bioconjugate Chem. 2006, 17, 524.
- (2006) Bioconjugate Chem. , vol.17 , pp. 524
- Kuroda, T.¹ Suenaga, K.² Sakakura, A.³ Handa, T.⁴ Okamoto, K.⁵ Kigoshi, H.⁶

37
- 31444433185
- K. Hirata, S. Muraoka, K. Suenaga, K. Kuroda, K. Kato, H. Tanaka, M. Yamamoto, M. Takata, K. Yamada, H. Kigoshi, J. Mol. Biol. 2006, 356, 945.
- (2006) J. Mol. Biol. , vol.356 , pp. 945
- Hirata, K.¹ Muraoka, S.² Suenaga, K.³ Kuroda, K.⁴ Kato, K.⁵ Tanaka, H.⁶ Yamamoto, M.⁷ Takata, M.⁸ Yamada, K.⁹ Kigoshi, H.¹⁰

38
- 0345059373
- V. A. Klenchin, J. S. Allingham, R. King, J. Tanaka, G. Marriott, I. Rayment, Nat. Struct. Biol. 2003, 10, 1058.
- (2003) Nat. Struct. Biol. , vol.10 , pp. 1058
- Klenchin, V.A.¹ Allingham, J.S.² King, R.³ Tanaka, J.⁴ Marriott, G.⁵ Rayment, I.⁶

39
- 26844450126
- J. S. Allingham, A. Zampella, M. V. D'Auria, I. Rayment, Proc. Natl. Acad. Sci. USA 2005, 102, 14527.
- (2005) Proc. Natl. Acad. Sci. USA , vol.102 , pp. 14527
- Allingham, J.S.¹ Zampella, A.² D'Auria, M.V.³ Rayment, I.⁴

40
- 15744362287
- V. A. Klenchin, R. King, J. Tanaka, G. Marriott, I. Rayment, Chem. Biol. 2005, 12, 287.
- (2005) Chem. Biol. , vol.12 , pp. 287
- Klenchin, V.A.¹ King, R.² Tanaka, J.³ Marriott, G.⁴ Rayment, I.⁵

41
- 33645453004
- S. A. Rizvi, V. Tereshko, A. A. Kossiakoff, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 3882.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 3882
- Rizvi, S.A.¹ Tereshko, V.² Kossiakoff, A.A.³ Kozmin, S.A.⁴

42
- 77955851838
- references therein.
- M. Kita, H. Watanabe, T. Ishitsuka, Y. Mogi, H. Kigoshi, Tetrahedron Lett. 2010, 51, 4882, and references therein.
- (2010) Tetrahedron Lett. , vol.51 , pp. 4882
- Kita, M.¹ Watanabe, H.² Ishitsuka, T.³ Mogi, Y.⁴ Kigoshi, H.⁵

43
- 0032568650
- R. D. Mullins, J. A. Heuser, T. D. Pollard, Proc. Natl. Acad. Sci. USA 1998, 95, 6181
- (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 6181
- Mullins, R.D.¹ Heuser, J.A.² Pollard, T.D.³

44
- 0034720293
- L. Blanchoin, K. J. Amann, H. N. Higgs, J. B. Marchand, D. A. Kaiser, T. D. Pollard, Nature 2000, 404, 1007.
- (2000) Nature , vol.404 , pp. 1007
- Blanchoin, L.¹ Amann, K.J.² Higgs, H.N.³ Marchand, J.B.⁴ Kaiser, D.A.⁵ Pollard, T.D.⁶

45
- 33749037156
- For a review on the Arp2/3 complex, see.
- For a review on the Arp2/3 complex, see:, E. D. Goley, M. D. Welch, Nat. Rev. Mol. Cell Biol. 2006, 7, 713.
- (2006) Nat. Rev. Mol. Cell Biol. , vol.7 , pp. 713
- Goley, E.D.¹ Welch, M.D.²

46
- 0035941045
- R. C. Robinson, K. Turbedsky, D. A. Kaiser, J. B. Marchand, H. N. Higgs, S. Choe, T. D. Pollard, Science 2001, 294, 1679.
- (2001) Science , vol.294 , pp. 1679
- Robinson, R.C.¹ Turbedsky, K.² Kaiser, D.A.³ Marchand, J.B.⁴ Higgs, H.N.⁵ Choe, S.⁶ Pollard, T.D.⁷

47
- 69249212192
- B. J. Nolen, N. Tomasevic, A. Russell, D. W. Pierce, Z. Jia, C. D. McCormick, J. Hartman, R. Sakowicz, T. D. Pollard, Nature 2009, 460, 1031.
- (2009) Nature , vol.460 , pp. 1031
- Nolen, B.J.¹ Tomasevic, N.² Russell, A.³ Pierce, D.W.⁴ Jia, Z.⁵ McCormick, C.D.⁶ Hartman, J.⁷ Sakowicz, R.⁸ Pollard, T.D.⁹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.