Abstract
Various aspects of interaction of the antitumour glycopeptide antibiotic bleomycin with nucleic acids are considered. Data on equilibrium binding parameters obtained by various physicochemical methods have been collected and compared. The contribution of N- and C-terminal domains of the glycopeptide molecule to the binding with DNA and sequence specificity of DNA cleavage are discussed. Data on a recently created new class of compounds – bleomycin – oligonucleotide conjugates – are presented. These compounds, like antibiotics, possess DNA-cleaving activity (also in a catalytic manner) together with high selectivity towards a selected nucleotide sequence. The bibliography includes 267 references.
References
1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) ,
1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
5.
Umezawa H., Ishizuka M., Maeda K., Takeuchi T.
Cancer ,
1967
6.
SUZUKI H., NAGAI K., YAMAKI H., TANAKA N., UMEZAWA H.
Journal of Antibiotics ,
2012
7.
UMEZAWA H., ISHIZUKA M., KIMURA K., IWANAGA J., TAKEUCHI T.
Journal of Antibiotics ,
1968
8.
TAKEUCHI M., YAMAMOTO T.
Journal of Antibiotics ,
1968
9.
9
V. H. Lynch
Carnegie Inst. Year Book ,
1954
10.
Mosher M.B., Deconti R.C., Bertino J.R.
Cancer ,
1972
11.
Rudders R.A.
Blood ,
1972
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
13.
Blum R.H., Carter S.K., Agre K.
Cancer ,
1973
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. ,
1958
15.
15
A. S. Holt
"Research in Photosynthesis" ,
1957
16.
17.
Müller W.E., Zahn R.K.
Progress in Nucleic Acid Research and Molecular Biology ,
1977
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1959
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1954
21.
WATANABE M., TAKABE Y., KATSUMATA T., TERASIMA T., UMEZAWA H.
Journal of Antibiotics ,
1973
22.
Yamazaki Z., Müller W.E., Zahn R.K.
Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis ,
1973
23.
SARTIANO G.P., WINKELSTEIN A., LYNCH W., BOGGS S.S.
Journal of Antibiotics ,
1973
24.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR ,
1951
25.
Onishi T., Shimada K., Takagi Y.
Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis ,
1973
26.
MIYAKI M., KITAYAMA T., ONO T.
Journal of Antibiotics ,
1974
27.
TAKITA T., MURAOKA Y., YOSHIOKA T., FUJII A., MAEDA K., UMEZAWA H.
Journal of Antibiotics ,
2012
28.
TAKITA T., MURAOKA Y., NAKATANI T., FUJII A., UMEZAWA Y., NAGANAWA H., UMEZAWA H.
Journal of Antibiotics ,
2012
29.
Takita T., Umezawa Y., Saito S., Morishima H., Naganawa H., Umezawa H., Tsuchiya T., Miyake T., Kageyama S., Umezawa S., Muraoka Y., Suzuki M., Otsuka M., Narita M., Kobayashi S., et. al.
Tetrahedron Letters ,
1982
30.
Nagai K., Yamaki H., Suzuki H., Tanaka N., Umezawa H.
Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis ,
1969
31.
NAGAI K., SUZUKI H., TANAKA N., UMEZAWA H.
Journal of Antibiotics ,
1969
32.
NAGAI K., SUZUKI H., TANAKA N., UMEZAWA H.
Journal of Antibiotics ,
1969
33.
SUZUKI H., NAGAI K., YAMAKI H., TANAKA N., UMEZAWA H.
Journal of Antibiotics ,
2012
34.
SUZUKI H., NAGAI K., AKUTSU E., YAMAKI H., TANAKA N., UMEZAWA H.
Journal of Antibiotics ,
2012
35.
Sausville E.A., Peisach J., Horwitz S.B.
Biochemical and Biophysical Research Communications ,
1976
36.
Sausville E.A., Peisach J., Horwitz S.B.
Biochemistry ,
1978
37.
Sausville E.A., Stein R.W., Peisach J., Horwitz S.B.
Biochemistry ,
1978
38.
Chien M., Grollman A.P., Horwitz S.B.
Biochemistry ,
1977
39.
TAKITA T., MURAOKA Y., NAKATANI T., FUJII A., IITAKA Y., UMEZAWA H.
Journal of Antibiotics ,
2012
40.
Glickson J.D., Pillai R.P., Sakai T.T.
Proceedings of the National Academy of Sciences of the United States of America ,
1981
41.
Petering D.H., Byrnes R.W., Antholine W.E.
Chemico-Biological Interactions ,
1990
42.
Dabrowiak J.C., Greenaway F.T., Longo W.E., Van Husen M., Crooke S.T.
Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis ,
1978
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. ,
1870
44.
Dabrowiak J.C.
Journal of Inorganic Biochemistry ,
1980
45.
Sugiura Y., Suzuki T., Otsuka M., Kobayashi S., Ohno M., Takita T., Umezawa H.
Journal of Biological Chemistry ,
1983
46.
Kittaka A., Sugano Y., Otsuka M., Ohno M., Sugiura Y., Umezawa H.
Tetrahedron Letters ,
1986
47.
Povirk L.F., Hogan M., Dattagupta N.
Biochemistry ,
1979
48.
Povirk L.F., Hogan M., Dattagupta N., Buechner M.
Biochemistry ,
1981
49.
49
A. A. Krasnovskii
Biofizika ,
1958
50.
Albertini J.P., Garnier-Suillerot A.
Biochemistry ,
1982
51.
Albertini J.P., Garnier-Suillerot A.
Biochemistry ,
1984
52.
HIROAKI H., NAKAYAMA T., IKEHARA M., UESUGI S.
Chemical and Pharmaceutical Bulletin ,
2011
53.
53
D. Porretand E. Rabinowitch
Nature ,
1937
54.
Huang C., Galvan L., Crooke S.T.
Biochemistry ,
1980
55.
Boger D.L., Colletti S.L., Honda T., Menezes R.F.
Journal of the American Chemical Society ,
1994
56.
Caspary W.J., Lanzo D.A., Niziak C.
Biochemistry ,
1982
57.
KASAI H., NAGANAWA H., TAKITA T., UMEZAWA H.
Journal of Antibiotics ,
2012
58.
Sakai T.T., Riordan J.M., Glickson J.D.
Biochemistry ,
1982
59.
Chang C.H., Meares C.F.
Biochemistry ,
1984
60.
Sakai T.T., Riordan J.M., Booth T.E., Glickson J.D.
Journal of Medicinal Chemistry ,
1981
61.
61
A. N. Terenin
1959
62.
UMEZAWA H., ASAKURA H., ODA K., HORI S., HORI M.
Journal of Antibiotics ,
2012
63.
ASAKURA H., HORI M., UMEZAWA H.
Journal of Antibiotics ,
1975
64.
64
Chem. Zentr. II ,
1931
65.
Carter B.J., de Vroom E., Long E.C., van der Marel G.A., van Boom J.H., Hecht S.M.
Proceedings of the National Academy of Sciences of the United States of America ,
1990
66.
Stubbe J., Kozarich J.W.
Chemical Reviews ,
1987
67.
Chen D.M., Sakai T.T., Glickson J.D., Patel D.J.
Biochemical and Biophysical Research Communications ,
1980
68.
Pillai R.P., Rama Krishna N., Sakai T.T., Glickson J.D.
Biochemical and Biophysical Research Communications ,
1980
69.
Sakai T.T., Riordan J.M., Kumar N.G., Haberle F.J., Elgavish G.A., Glickson J.D., Levy A.
Journal of Biomolecular Structure and Dynamics ,
1983
70.
Sakai T.T., Riordan J.M., Glickson J.D.
Biochimica et Biophysica Acta - General Subjects ,
1983
71.
Booth T.E., Sakai T.T., Glickson J.D.
Biochemistry ,
1983
72.
Gamcsik M.P., Glickson J.D., Zon G.
Journal of Biomolecular Structure and Dynamics ,
1990
73.
Urata H., Ueda Y., Usami Y., Akagi M.
Journal of the American Chemical Society ,
1993
74.
Wu W., Vanderwall D.E., Stubbe J., Kozarich J.W., Turner C.J.
Journal of the American Chemical Society ,
1994
75.
Manderville R.A., Ellena J.F., Hecht S.M.
Journal of the American Chemical Society ,
1994
76.
Kross J., Henner W.D., Haseltine W.A., Rodriquez L., Levin M.D., Hecht S.M.
Biochemistry ,
1982
77.
Fisher L.M., Kuroda R., Sakai T.T.
Biochemistry ,
1985
78.
Kilkuskie R.E., Suguna H., Yellin B., Murugesan N., Hecht S.M.
Journal of the American Chemical Society ,
1985
79.
Farinas E., Tan J.D., Baidya N., Mascharak P.K.
Journal of the American Chemical Society ,
1993
80.
Guajardo R.J., Hudson S.E., Brown S.J., Mascharak P.K.
Journal of the American Chemical Society ,
1993
81.
Boger D.L., Honda T., Menezes R.F., Colletti S.L.
Journal of the American Chemical Society ,
1994
82.
MURAOKA Y., FUJII A., YOSHIOKA T., TAKITA T., UMEZAWA H.
Journal of Antibiotics ,
2012
83.
SUGIURA Y., ISHIZU K., MIYOSHI K.
Journal of Antibiotics ,
2012
84.
Berry D.E., Chang L.H., Hecht S.M.
Biochemistry ,
1985
85.
Levy M.J., Hecht S.M.
Biochemistry ,
1988
86.
Antholine W.E., Petering D.H., Saryan L.A., Brown C.E.
Proceedings of the National Academy of Sciences of the United States of America ,
1981
87.
Antholine W.E., Petering D.H.
Biochemical and Biophysical Research Communications ,
1979
88.
Sugiura Y.
Journal of Inorganic Biochemistry ,
1979
89.
Burger R.M., Peisach J., Horwitz S.B.
Journal of Biological Chemistry ,
1981
90.
SUGIURA Y.
Journal of Antibiotics ,
2012
91.
Sugiura Y.
Journal of the American Chemical Society ,
1980
92.
Chikira M., Antholine W.E., Petering D.H.
Journal of Biological Chemistry ,
1989
93.
IITAKA Y., NAKAMURA H., NAKATANI T., MURAOKA Y., FUJII A., TAKITA T., UMEZAWA H.
Journal of Antibiotics ,
2012
94.
Akkerman M.A., Neijman E.W., Wijmenga S.S., Hilbers C.W., Bermel W.
Journal of the American Chemical Society ,
1990
95.
Shields H., McGlumphy C., Hamrick P.J.
Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression ,
1982
96.
Chikira M., Sato T., Antholine W.E., Petering D.H.
Journal of Biological Chemistry ,
1991
97.
Shields H., Charles M.
Biochimica et Biophysica Acta - General Subjects ,
1984
98.
98
W. Franke
Chem. Zentr. ,
1954
99.
Neidle S., Abraham Z.
Critical Reviews in Biochemistry ,
1984
100.
Waring M.J.
Annual Review of Biochemistry ,
1981
101.
TAKITA T., MURAOKA Y., FUJII A., ITOH H., MAEDA K., UMEZAWA H.
Journal of Antibiotics ,
2012
102.
Lin S.Y., Grollman A.P.
Biochemistry ,
1981
103.
Miller K.J., Lauer M., Caloccia W.
Biopolymers ,
1985
104.
Hénichart J., Bernier J., Helbecque N., Houssin R.
Nucleic Acids Research ,
1985
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR ,
1958
106.
106
F. Fichter
Helv. Chim. Acta ,
1927
107.
Bernier J.L., Henichart J.P., Catteau J.P.
Analytical Biochemistry ,
1981
108.
Krugh T.R., Wittlin F.N., Cramer S.P.
Biopolymers ,
1975
109.
Patel D.J.
Accounts of Chemical Research ,
1979
110.
Feigon J., Denny W.A., Leupin W., Kearns D.R.
Journal of Medicinal Chemistry ,
1984
111.
Wilson W.D., Jones R.L.
Nucleic Acids Research ,
1982
112.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. ,
1952
113.
Murakami H., Mori H., Taira S.
Journal of Theoretical Biology ,
1976
114.
Gabbay E.J., Adawadkar P.D., Wilson W.D.
Biochemistry ,
1976
115.
Kuroda R., Neidle S., Riordan J.M., Sakai T.T.
Nucleic Acids Research ,
1982
116.
Riordan J.M., Sakai T.T.
Journal of Medicinal Chemistry ,
1983
117.
117
V. V. Levchenko
Zhur. Obshch. Khim. ,
1948
118.
Sugiura Y., Suzuki T.
Journal of Biological Chemistry ,
1982
119.
Sugiyama H., Kilkuskie R.E., Hecht S.M., Van der Marel G.A., Van Boom J.H.
Journal of the American Chemical Society ,
1985
120.
Yamamoto K., Kawanishi S.
Biochemical and Biophysical Research Communications ,
1992
121.
Sobell H.M., Jain S.C.
Journal of Molecular Biology ,
1972
122.
Suzuki T., Kuwahara J., Sugiura Y.
Biochemical and Biophysical Research Communications ,
1983
123.
Hertzberg R.P., Caranfa M.J., Hecht S.M.
Biochemistry ,
1988
124.
Kuwahara J., Sugiura Y.
Proceedings of the National Academy of Sciences of the United States of America ,
1988
125.
Petrusek R.L., Anderson G.L., Garner T.F., Fannin Q.L., Kaplan D.J., Zimmer S.G., Hurley L.H.
Biochemistry ,
1981
126.
Nightingale K.P., Fox K.R.
Nucleic Acids Research ,
1993
127.
Murakami H., Mori H., Taira S.
Journal of Theoretical Biology ,
1973
128.
ONISHI T., IWATA H., TAKAGI Y.
Journal of Biochemistry ,
1975
129.
Ishida R., Takahashi T.
Biochemical and Biophysical Research Communications ,
1975
130.
William Lown J., Sim S.
Biochemical and Biophysical Research Communications ,
1977
131.
131
N. Thooi
Compt. rend. ,
1958
132.
Sugiura Y.
Journal of the American Chemical Society ,
1980
133.
SUGIURA Y., KIKUCHI T.
Journal of Antibiotics ,
2012
134.
Oberley L.W., Buettner G.R.
FEBS Letters ,
1979
135.
Lown J.W., Joshua A.V.
Biochemical Pharmacology ,
1980
136.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1954
137.
Rodriguez L.O., Hecht S.M.
Biochemical and Biophysical Research Communications ,
1982
138.
Burger R.M., Peisach J., Blumberg W.E., Horwitz S.B.
Journal of Biological Chemistry ,
1979
139.
KURAMOCHI H., TAKAHASHI K., TAKITA T., UMEZAWA H.
Journal of Antibiotics ,
2012
140.
Pratviel G., Bernadou J., Meunier B.
Biochemical Pharmacology ,
1989
141.
141
Friedl.
142.
Natrajan A., Hecht S.M., Van der Marel G.A., Van Boom J.H.
Journal of the American Chemical Society ,
1990
143.
Sam J.W., Tang X., Peisach J.
Journal of the American Chemical Society ,
1994
144.
Hecht S.M.
Accounts of Chemical Research ,
1986
145.
Knorre D.G., Fedorova O.S., Frolova E.I.
Russian Chemical Reviews ,
1993
146.
Giloni L., Takeshita M., Johnson F., Iden C., Grollman A.P.
Journal of Biological Chemistry ,
1981
147.
Wu J.C., Kozarich J.W., Stubbe J.
Journal of Biological Chemistry ,
1983
148.
Wu J.C., Kozarich J.W., Stubbe J.
Biochemistry ,
1985
149.
Kozarich J.W., Worth L., Frank B.L., Christner D.F., Vanderwall D.E., Stubbe J.
Science ,
1989
150.
Worth L., Frank B.L., Christner D.F., Absalon M.J., Stubbe J., Kozarich J.W.
Biochemistry ,
1993
151.
Uesugi S., Shida T., Ikehara M., Kobayashi Y., Kyogoku Y.
Nucleic Acids Research ,
1984
152.
Murugesan N., Xu C., Ehrenfeld G.M., Sugiyama H., Kilkuskie R.E., Rodriguez L.O., Chang L.H., Hecht S.M.
Biochemistry ,
1985
153.
Rabow L.E., Stubbe J., Kozarich J.W., McGall G.H.
Journal of the American Chemical Society ,
1990
154.
Wu J.C., Stubbe J., Kozarich J.W.
Biochemistry ,
1985
155.
Structure of the alkali-labile product formed during iron(II)-bleomycin-mediated DNA strand scission
Sugiyama H., Xu C., Murugesan N., Hecht S.M.
Journal of the American Chemical Society ,
1985
156.
Sugiyama H., Xu C., Murugesan N., Hecht S.M., Van der Marel G.A., Van Boom J.H.
Biochemistry ,
1988
157.
Rabow L.E., Stubbe J., Kozarich J.W.
Journal of the American Chemical Society ,
1990
158.
Burger R.M., Peisach J., Horwitz S.B.
Journal of Biological Chemistry ,
1982
159.
Absalon M.J., Krishnamoorthy C.R., McGall G., Kozarich J.W., Stubbe J.
Nucleic Acids Research ,
1992
160.
Gajewski E., Aruoma O.I., Dizdaroglu M., Halliwell B.
Biochemistry ,
1991
161.
KOHDA K., KASAI H., OGAWA T., SUZUKI T., KAWAZOE Y.
Chemical and Pharmaceutical Bulletin ,
2011
162.
Maxam A.M., Gilbert W.
Proceedings of the National Academy of Sciences of the United States of America ,
1977
163.
164
1917
164.
165
Friedl.
165.
Povirk L.F., Köhnlein W., Hutchinson F.
Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis ,
1978
166.
167
Friedl.
167.
Kross J., Henner W.D., Hecht S.M., Haseltine W.A.
Biochemistry ,
1982
168.
169
Friedl.
169.
Comparison of the sequence specificity of bleomycin cleavage in two slightly different DNA sequences
Murray V., Martin R.F.
Nucleic Acids Research ,
1985
170.
Lloyd R.S., Haidle C.W., Robberson D.L.
Biochemistry ,
1978
171.
Lloyd R.S., Haidle C.W., Robberson D.L.
Gene ,
1979
172.
173
Friedl.
173.
Mirabelli C.K., Huang C.H., Crooke S.T.
Biochemistry ,
1983
174.
Griinwade J.E., Cason E.B., Beerman T.A.
Nucleic Acids Research ,
1987
175.
Mascharak P.K., Sugiura Y., Kuwahara J., Suzuki T., Lippard S.J.
Proceedings of the National Academy of Sciences of the United States of America ,
1983
176.
Gold B., Dange V., Moore M.A., Eastman A., Van der Marel G.A., Van Boom J.H., Hecht S.M.
Journal of the American Chemical Society ,
1988
177.
Williams L.D., Goldberg I.H.
Biochemistry ,
1988
178.
Murray V., Tan L., Matthews J., Martin R.F.
Journal of Biological Chemistry ,
1988
179.
Hertzberg R.P., Caranfa M.J., Hecht S.M.
Biochemistry ,
1985
180.
Behe M., Felsenfeld G.
Proceedings of the National Academy of Sciences of the United States of America ,
1981
181.
Long E.C., Hecht S.M., Van der Marel G.A., Van Boom J.H.
Journal of the American Chemical Society ,
1990
182.
Muller W.E., Yamazaki Z., Breter H., Zahn R.K.
FEBS Journal ,
1972
183.
184
F. Haurowitz
"The Chemistry and Function of Proteins" ,
1965
184.
Haidle C.W., Bearden J.
Biochemical and Biophysical Research Communications ,
1975
185.
Krishnamoorthy C.R., Vanderwall D.E., Kozarich J.W., Stubbe J.
Journal of the American Chemical Society ,
1988
186.
Haidle C.W., Kuo M.T., Weiss K.K.
Biochemical Pharmacology ,
1972
187.
Carter B.J., Reddy K.S., Hecht S.M.
Tetrahedron ,
1991
188.
Carter B.J., Holmes C.E., Van Atta R.B., Dange V., Hecht S.M.
Nucleosides and Nucleotides ,
1991
189.
Hüttenhofer A., Hudson S., Noller H.F., Mascharak P.K.
Journal of Biological Chemistry ,
1992
190.
Holmes C.E., Carter B.J., Hecht S.M.
Biochemistry ,
1993
191.
Duff R.J., de Vroom E., Geluk A., Hecht S.M., van der Marel G.A., van Boom J.H.
Journal of the American Chemical Society ,
1993
192.
Holmes C.E., Hecht S.M.
Journal of Biological Chemistry ,
1993
193.
Hecht S.M.
Bioconjugate Chemistry ,
1994
194.
Morgan M.A., Hecht S.M.
Biochemistry ,
1994
195.
197
J. Sicher
Chem. Listy ,
1955
196.
Takeshita M., Kappen L.S., Grollman A.P., Eisenberg M., Goldberg I.H.
Biochemistry ,
1981
197.
Morii T., Matsuura T., Saito I., Suzuki T., Kuwahara J., Sugiura Y.
Journal of the American Chemical Society ,
1986
198.
Morii T., Saito I., Matsuura T., Kuwahara J., Sugiura Y.
Journal of the American Chemical Society ,
1987
199.
Sugiyama H., Ehrenfeld G.M., Shipley J.B., Kilkuskie R.E., Chang L., Hecht S.M.
Journal of Natural Products ,
1985
200.
Sugiyama H., Kilkuskie R.E., Chang L.H., Ma L.T., Hecht S.M., Van der Marel G.A., Van Boom J.H.
Journal of the American Chemical Society ,
1986
201.
Oppenheimer N.J., Rodriguez L.O., Hecht S.M.
Proceedings of the National Academy of Sciences of the United States of America ,
1979
202.
Oppenheimer N.J., Chang C., Chang L.H., Ehrenfeld G., Rodriguez L.O., Hecht S.M.
Journal of Biological Chemistry ,
1982
203.
Shipley J.B., Hecht S.M.
Chemical Research in Toxicology ,
1988
204.
NAKAYAMA Y., KUNISHIMA M., OMOTO S., TAKITA T., UMEZAWA H.
Journal of Antibiotics ,
2012
205.
MURAOKA Y., KOBAYASHI H., FUJII A., KUNISHIMA M., FUJII T., NAKAYAMA Y., TAKITA T., UMEZAWA H.
Journal of Antibiotics ,
2012
206.
Ehrenfeld G.M., Shipley J.B., Heimbrook D.C., Sugiyama H., Long E.C., Van Boom J.H., Van der Marel G.A., Oppenheimer N.J., Hecht S.M.
Biochemistry ,
1987
207.
McLean M.J., Dar A., Waring M.J.
Journal of Molecular Recognition ,
1989
208.
Suzuki T., Kuwahara J., Goto M., Sugiura Y.
Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression ,
1985
209.
Carter B.J., Murty V.S., Reddy K.S., Wang S.N., Hecht S.M.
Journal of Biological Chemistry ,
1990
210.
KONISHI M., SAITO K., NUMATA K., TSUNO T., ASAMA K., TSUKIURA H., NAITO T., KAWAGUCHI H.
Journal of Antibiotics ,
2012
211.
Mirabelli C., Mong S., Huang C., Crooke S.T.
Biochemical and Biophysical Research Communications ,
1979
212.
Mirabelli C.K., Huang C., Prestayko A.W., Crooke S.T.
Cancer Chemotherapy and Pharmacology ,
1982
213.
215
N. D. Tomashov
Zh. Prikl. Khim. ,
1970
214.
Sugano Y., Kittaka A., Otsuka M., Ohno M., Sugiura Y., Umezawa H.
Tetrahedron Letters ,
1986
215.
217
1925
216.
Otsuka M., Kittaka A., Ohno M., Suzuki T., Kuwahara J., Sugiura Y., Umezawa H.
Tetrahedron Letters ,
1986
217.
Kittaka A., Sugano Y., Otsuka M., Ohno M.
Tetrahedron ,
1988
218.
Otsuka M., Masuda T., Haupt A., Ohno M., Shiraki T., Sugiura Y., Maeda K.
Journal of the American Chemical Society ,
1990
219.
Kopka M.L., Yoon C., Goodsell D., Pjura P., Dickerson R.E.
Proceedings of the National Academy of Sciences of the United States of America ,
1985
220.
Hamamichi N., Natrajan A., Hecht S.M.
Journal of the American Chemical Society ,
1992
221.
223
1959
222.
Kane S.A., Natrajan A., Hecht S.M.
Journal of Biological Chemistry ,
1994
223.
Fox K.R., Grigg G.W., Waring M.J.
Biochemical Journal ,
1987
224.
226
Chem. Abs. ,
1961
225.
Nightingale K.P., Fox K.R.
Biochemical Journal ,
1992
226.
Klug A., Jack A., Viswamitra M.A., Kennard O., Shakked Z., Steitz T.A.
Journal of Molecular Biology ,
1979
227.
229
1959
228.
230
Chem. Abs. ,
1962
229.
231
1960
230.
232
Chem. Abs. ,
1960
231.
Goodchild J.
Bioconjugate Chemistry ,
1990
232.
Hélène C., Toulmé J.
Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression ,
1990
233.
235
R. Peffen
1967
234.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. ,
1969
235.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. ,
1969
236.
TAKITA T., FUJII A., FUKUOKA T., UMEZAWA H.
Journal of Antibiotics ,
2012
237.
239
Mendelbaum H. G.
Bull. Soc. chim. France ,
1973
238.
Zarytova V.F., Sergeyev D.S., Godovikova T.S.
Bioconjugate Chemistry ,
1993
239.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" ,
1954
240.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) ,
1958
241.
SERGEEV D.S., ZARYTOVA V.F., MAMAEV S.V., GODOVIKOVA T.S., VLASSOV V.V.
Antisense Research and Development ,
2016
242.
Vlassov V.V., Zarytova V.F., Kutiavin I.V., Mamaev S.V., Podyminogin M.A.
Nucleic Acids Research ,
1986
243.
245
G. A. Meerson
1958
244.
Hélène C.
Current Opinion in Biotechnology ,
1993
245.
Fedorova O.S., Knorre D.G., Podust L.M., Zarytova V.F.
FEBS Letters ,
1988
246.
Povsic T.J., Strobel S.A., Dervan P.B.
Journal of the American Chemical Society ,
1992
247.
Takasugi M., Guendouz A., Chassignol M., Decout J.L., Lhomme J., Thuong N.T., Hélène C.
Proceedings of the National Academy of Sciences of the United States of America ,
1991
248.
Strobel S.A., Dervan P.B.
Science ,
1990
249.
François J.C., Saison-Behmoaras T., Barbier C., Chassignol M., Thuong N.T., Hélène C.
Proceedings of the National Academy of Sciences of the United States of America ,
1989
250.
252
D. Goerrig
1956
251.
Arnott S., Selsing E.
Journal of Molecular Biology ,
1974
252.
Pilch D.S., Levenson C., Shafer R.H.
Proceedings of the National Academy of Sciences of the United States of America ,
1990
253.
255
Tomita M
Chem. Abs. ,
1939
254.
Hertzberg R.P., Dervan P.B.
Biochemistry ,
1984
255.
Van Atta R.B., Bernadou J., Meunier B., Hecht S.M.
Biochemistry ,
1990
256.
Murugesan N., Ehrenfeld G.M., Hecht S.M.
Journal of Biological Chemistry ,
1982
257.
Murugesan N., Hecht S.M.
Journal of the American Chemical Society ,
1985
258.
260
C. Friedel
Compt. rend. ,
1876
259.
Buettner G.R., Moseley P.L.
Biochemistry ,
1992
260.
Povirk L.F.
Biochemistry ,
1979
261.
Aruoma O.I., Halliwell B., Gajewski E., Dizdaroglu M.
Journal of Biological Chemistry ,
1989
262.
Dizdaroglu M., Aruoma O.I., Halliwell B.
Biochemistry ,
1990
263.
265
E. A. Ostroumov
Zavod. Lab. ,
1935
264.
266
N. G. Mudrik
1975
265.
Ueda K., Kobayashi S., Sakai H., Komano T.
Journal of Biological Chemistry ,
1985
266.
Sugiyama H., Sera T., Dannoue Y., Marumoto R., Saito I.
Journal of the American Chemical Society ,
1991