JPH01500189A - ２，７‐ジアザピレニウムジカチオンによる核酸の光切断法および新規ジアザピレン誘導体 - Google Patents

２，７‐ジアザピレニウムジカチオンによる核酸の光切断法および新規ジアザピレン誘導体

Info

Publication number: JPH01500189A
Authority: JP; Japan
Prior art keywords: formula; group; tables; groups; derivative
Prior art date: 1986-04-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP62502670A

Other languages

English (en)

Japanese (ja)

Inventor

レーン　ジャン　マリー

ジャズヴィンスキー　ジャロースロー

ブラッカー　ジョン

Original Assignee

コムパニー　オーリス　アンデュストリエ

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-04-29

Filing date

1987-04-29

Publication date

1989-01-26

1987-04-29 Application filed by コムパニー　オーリス　アンデュストリエ filed Critical コムパニー　オーリス　アンデュストリエ

1989-01-26 Publication of JPH01500189A publication Critical patent/JPH01500189A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 59
PODJSIAAYWCBDV-UHFFFAOYSA-N 5,6-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene Chemical class C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C43 PODJSIAAYWCBDV-UHFFFAOYSA-N 0.000 title claims description 55
108020004707 nucleic acids Proteins 0.000 title claims description 8
150000007523 nucleic acids Chemical class 0.000 title claims description 8
102000039446 nucleic acids Human genes 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 17
239000000126 substance Substances 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000001931 aliphatic group Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
229910052757 nitrogen Chemical group 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 6
150000002430 hydrocarbons Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000004149 thio group Chemical group *S* 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
-1 sulfonato ion Chemical class 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000004020 conductor Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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239000002904 solvent Substances 0.000 description 18
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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238000006467 substitution reaction Methods 0.000 description 5
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
150000003949 imides Chemical class 0.000 description 4
FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
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HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
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UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 3
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
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GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 3
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FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
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108010092160 Dactinomycin Proteins 0.000 description 2
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VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
240000006409 Acacia auriculiformis Species 0.000 description 1
229920000936 Agarose Polymers 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
ZPIPUFJBRZFYKJ-UHFFFAOYSA-N C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 Chemical compound C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 ZPIPUFJBRZFYKJ-UHFFFAOYSA-N 0.000 description 1
108020004638 Circular DNA Proteins 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
230000001482 DNA photocleavage Effects 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
241001071861 Lethrinus genivittatus Species 0.000 description 1
101710163270 Nuclease Proteins 0.000 description 1
BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
DPKHZNPWBDQZCN-UHFFFAOYSA-N acridine orange free base Chemical compound C1=CC(N(C)C)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 DPKHZNPWBDQZCN-UHFFFAOYSA-N 0.000 description 1
239000011543 agarose gel Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000007872 degassing Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000012154 double-distilled water Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
230000005281 excited state Effects 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000012634 fragment Substances 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
239000003550 marker Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
QHADMMAFBAZFTE-UHFFFAOYSA-N naphtho[2,1,8-def]quinoline Chemical class C1=CN=C2C=CC3=CC=CC4=CC=C1C2=C43 QHADMMAFBAZFTE-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000004713 phosphodiesters Chemical class 0.000 description 1
230000002186 photoactivation Effects 0.000 description 1
230000008832 photodamage Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
229960003857 proglumide Drugs 0.000 description 1
239000001294 propane Substances 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
108091008146 restriction endonucleases Proteins 0.000 description 1
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
229920002477 rna polymer Polymers 0.000 description 1
229910052711 selenium Inorganic materials 0.000 description 1
239000011669 selenium Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
238000013519 translation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Saccharide Compounds (AREA)
Photoreceptors In Electrophotography (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

JP62502670A 1986-04-29 1987-04-29 ２，７‐ジアザピレニウムジカチオンによる核酸の光切断法および新規ジアザピレン誘導体 Pending JPH01500189A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR86/06212		1986-04-29
FR8606212A FR2597871B1 (fr)	1986-04-29	1986-04-29	Procede de photoclivage des acides nucleiques a l'aide de dications 2,7-diazapyrenium, nouveaux derives diazapyreniques

Publications (1)

Publication Number	Publication Date
JPH01500189A true JPH01500189A (ja)	1989-01-26

Family

ID=9334745

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP62502670A Pending JPH01500189A (ja)	1986-04-29	1987-04-29	２，７‐ジアザピレニウムジカチオンによる核酸の光切断法および新規ジアザピレン誘導体

Country Status (7)

Country	Link
US (1)	US4925937A (de)
EP (1)	EP0244320B1 (de)
JP (1)	JPH01500189A (de)
AT (1)	ATE78036T1 (de)
DE (1)	DE3780206T2 (de)
FR (1)	FR2597871B1 (de)
WO (1)	WO1987006584A1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4967008A (en) *	1990-01-12	1990-10-30	Sherex Chemical Company, Inc.	Polyamines and their preparation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE755563A (fr) *	1969-09-02	1971-03-01	Polaroid Corp	Dispositif de filtrage variable de lumiere
US3853589A (en) *	1970-11-09	1974-12-10	Ici Ltd	Metal deposition process
ZA706357B (en) *	1970-09-17	1971-05-27	Ici Ltd	Radiation sensitive materials containing nitrogenous cationic compounds
DE3620332A1 (de) *	1986-06-18	1987-12-23	Bayer Ag	Verfahren zur herstellung von tetrachlornaphthalintetracarbonsaeuredianhydrid und -diimid, sowie die neue verbindung 2.3.6.7-tetrachlornaphthalin-1.4.5.8.- tetracarbonsaeurediimid

1986
- 1986-04-29 FR FR8606212A patent/FR2597871B1/fr not_active Expired - Lifetime
1987
- 1987-04-29 DE DE8787400980T patent/DE3780206T2/de not_active Expired - Fee Related
- 1987-04-29 EP EP87400980A patent/EP0244320B1/de not_active Expired - Lifetime
- 1987-04-29 AT AT87400980T patent/ATE78036T1/de not_active IP Right Cessation
- 1987-04-29 WO PCT/FR1987/000142 patent/WO1987006584A1/fr not_active Ceased
- 1987-04-29 JP JP62502670A patent/JPH01500189A/ja active Pending
- 1987-04-29 US US07/141,607 patent/US4925937A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0244320B1 (de)	1992-07-08
EP0244320A1 (de)	1987-11-04
WO1987006584A1 (fr)	1987-11-05
FR2597871B1 (fr)	1990-11-16
DE3780206D1 (de)	1992-08-13
US4925937A (en)	1990-05-15
DE3780206T2 (de)	1993-02-11
FR2597871A1 (fr)	1987-10-30
ATE78036T1 (de)	1992-07-15

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Wang et al.	2010	Nickel (II) and iron (III) selective off-on-type fluorescence probes based on perylene tetracarboxylic diimide
Palmer et al.	1990	DNA-directed alkylating agents. 2. Synthesis and biological activity of platinum complexes linked to 9-anilinoacridine
Arena et al.	1995	Synthesis, characterization, and Interaction with DNA of the Novel metallointercalator cationic complex (2, 2': 6', 2''-terpyridine) methylplatinum (II)
Král et al.	1996	Protonated sapphyrins. Highly effective phosphate receptors
McConnaughie et al.	1995	Novel acridine-triazenes as prototype combilexins: synthesis, DNA binding, and biological activity
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Prokhorov et al.	2011	1, 2, 4-Triazine method of bipyridine ligand synthesis for the preparation of new luminescent Eu (III) complexes
Das et al.	2022	Carbazole appended trans-dicationic pyridinium porphyrin finds supremacy in DNA binding/photocleavage over a non-carbazolyl analogue
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JPH01500189A (ja)	1989-01-26	２，７‐ジアザピレニウムジカチオンによる核酸の光切断法および新規ジアザピレン誘導体
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US6828439B1 (en)	2004-12-07	Compounds, composition, and methods for photodynamic therapy
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