ZA200700169B - Cationic bacteriochlorophyll derivatives and uses thereof - Google Patents
Cationic bacteriochlorophyll derivatives and uses thereof Download PDFInfo
- Publication number
- ZA200700169B ZA200700169B ZA200700169A ZA200700169A ZA200700169B ZA 200700169 B ZA200700169 B ZA 200700169B ZA 200700169 A ZA200700169 A ZA 200700169A ZA 200700169 A ZA200700169 A ZA 200700169A ZA 200700169 B ZA200700169 B ZA 200700169B
- Authority
- ZA
- South Africa
- Prior art keywords
- amide
- bacteriochlorophyll derivative
- alkyl
- compound
- methoxycarbonylmethyl
- Prior art date
Links
- -1 Cationic bacteriochlorophyll derivatives Chemical class 0.000 title claims description 142
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 410
- DSJXIQQMORJERS-AGGZHOMASA-M bacteriochlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC([C@H](CC)[C@H]3C)=[N+]4C3=CC3=C(C(C)=O)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 DSJXIQQMORJERS-AGGZHOMASA-M 0.000 claims description 211
- 229910052763 palladium Inorganic materials 0.000 claims description 189
- 150000001408 amides Chemical class 0.000 claims description 186
- 125000000217 alkyl group Chemical group 0.000 claims description 145
- 150000001875 compounds Chemical class 0.000 claims description 130
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 92
- 206010028980 Neoplasm Diseases 0.000 claims description 81
- 238000002428 photodynamic therapy Methods 0.000 claims description 69
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 63
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 238000011282 treatment Methods 0.000 claims description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 35
- 230000004962 physiological condition Effects 0.000 claims description 35
- 150000001768 cations Chemical class 0.000 claims description 34
- 229940125898 compound 5 Drugs 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
- 150000001413 amino acids Chemical class 0.000 claims description 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000000524 functional group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 24
- 230000003287 optical effect Effects 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 241000894006 Bacteria Species 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- 108010003118 Bacteriochlorophylls Proteins 0.000 claims description 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
- 239000003504 photosensitizing agent Substances 0.000 claims description 18
- 102000004169 proteins and genes Human genes 0.000 claims description 18
- 108090000623 proteins and genes Proteins 0.000 claims description 18
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 17
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 16
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- 150000004676 glycans Chemical class 0.000 claims description 13
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- 150000002482 oligosaccharides Chemical class 0.000 claims description 13
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- 239000005017 polysaccharide Substances 0.000 claims description 13
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
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- 150000001450 anions Chemical class 0.000 claims description 11
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 10
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 210000002307 prostate Anatomy 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
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- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 7
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- 150000002367 halogens Chemical class 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 claims description 7
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- 230000002147 killing effect Effects 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
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- 229910052718 tin Inorganic materials 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 6
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229940125844 compound 46 Drugs 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims description 6
- 239000012678 infectious agent Substances 0.000 claims description 6
- 150000002892 organic cations Chemical class 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 5
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- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims description 5
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- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims description 5
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 4
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims description 4
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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EP2008665A1 (fr) * | 2007-06-25 | 2008-12-31 | Steba Biotech N.V. | Formulation injectable pour thérapie photodynamique |
JP5620279B2 (ja) | 2008-02-27 | 2014-11-05 | イエダ リサーチ アンド デベロップメント カンパニー リミテッド | 壊死性腫瘍の光線力学的治療及び画像化のためのrgd−(バクテリオ)クロロフィルコンジュゲート |
ES2856698T3 (es) | 2011-08-23 | 2021-09-28 | Yeda Res & Dev | Fotosensibilizadores de (bacterio)clorofila para el tratamiento de enfermedades y trastornos oculares |
PL2971026T3 (pl) | 2013-03-11 | 2021-06-14 | Tookad Ip Sarl | Sposób wytwarzania bakteriochlorofilu a |
RU2548675C9 (ru) * | 2013-05-29 | 2015-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет тонких химических технологий имени М.В. Ломоносова" (МИТХТ им. М.В. Ломоносова) | Аминоамиды в ряду бактериохлорофилла a, обладающие фотодинамической активностью, и способ их получения |
JP6218073B2 (ja) * | 2013-11-26 | 2017-10-25 | 国立大学法人群馬大学 | 細胞・組織内酸素濃度測定のための高感度近赤外りん光イリジウム錯体 |
RU2549953C2 (ru) * | 2013-12-25 | 2015-05-10 | Федеральное государственное унитарное предприятие Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" (ФГУП "ГНЦ "НИОПИК") | Фотосенсибилизатор для фотодинамической терапии |
RU2610566C1 (ru) * | 2015-09-17 | 2017-02-13 | Сергей Сергеевич Брусов | Способ фотодинамической терапии локальных очагов инфекции |
CN105424857A (zh) * | 2015-12-01 | 2016-03-23 | 浙江汇能生物股份有限公司 | 一种二甲基半胱胺盐酸盐的高效液相色谱分析方法 |
WO2018102252A1 (en) * | 2016-11-30 | 2018-06-07 | North Carolina State University | Methods for making bacteriochlorin macrocycles comprising an annulated isocyclic ring and related compounds |
WO2022115443A1 (en) * | 2020-11-24 | 2022-06-02 | The Regents Of The University Of California | Mitochondria targeting quinolinium-drug conjugates and their self-assembling nanoformulations for cancer therapy |
CN115093422B (zh) * | 2022-06-15 | 2023-06-20 | 西北工业大学 | 一种基于代谢标记策略的新型光敏剂及其制备方法和应用 |
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US3050296A (en) * | 1960-12-19 | 1962-08-21 | Trimborn Hans | Transport roller for industrial furnaces |
US3203888A (en) * | 1961-04-24 | 1965-08-31 | Exxon Research Engineering Co | Treating athabaska sands utilizing a flotation gas |
DE2018970A1 (de) | 1970-04-21 | 1971-11-11 | Badische Anilin- & Soda Fabrik AG, 6700 Ludwigshafen | Verfahren zur Herstellung von beta-Aminoäthylsulfoniumverbindungen |
US5330741A (en) * | 1992-02-24 | 1994-07-19 | The Regents Of The University Of California | Long-wavelength water soluble chlorin photosensitizers useful for photodynamic therapy and diagnosis of tumors |
US5744598A (en) * | 1992-06-19 | 1998-04-28 | University Of Toledo | Imines of porphyrins, of porphyrin derivatives, and of related compounds, and pharmaceutical compositions containing such imines |
IL102645A (en) | 1992-07-26 | 1998-02-22 | Yeda Res & Dev | Chlorophyll and bacteriochlorophyll derivatives, their preparation and pharmaceutical compositions comprising them |
US6147195A (en) | 1993-07-26 | 2000-11-14 | Yeda Research And Development Co., Ltd. | Chlorophyll and bacteriochlorophyll derivatives, their preparation and pharmaceutical compositions comprising them |
IL116126A0 (en) * | 1995-11-24 | 1996-01-31 | Yeda Res & Dev | Process for the preparation of bacteriochlorophyllis some novel compounds of this type and pharmaceutical compositions comprising them |
US5770730A (en) | 1996-03-08 | 1998-06-23 | Health Research, Inc. | Synthesis of carbodimide analogs of chlorins and bacteriochlorins and their use for diagnosis and treatment of cancer |
WO2000033833A1 (en) * | 1998-12-09 | 2000-06-15 | Yeda Research And Development Co. Ltd. | Palladium-substituted bacteriochlorophyll derivatives and use thereof |
IL133253A0 (en) * | 1999-12-01 | 2001-04-30 | Yeda Res & Dev | Chlorophyll and bacteriochlorophyll esters, their preparation and pharmaceutical compositions comprising them |
US6573258B2 (en) | 2000-09-27 | 2003-06-03 | Frontier Scientific, Inc. | Photodynamic porphyrin antimicrobial agents |
AU2002312154B2 (en) * | 2001-06-01 | 2008-05-15 | Biolitec Pharma Marketing Ltd | Water-soluble porphyrin derivatives for photodynamic therapy, their use and manufacture |
US20030203888A1 (en) * | 2001-06-06 | 2003-10-30 | Boyle Ross William | Chromophores |
US20050020559A1 (en) | 2001-10-03 | 2005-01-27 | Robinson Byron C | Chlorin photosensitizing agents for use in photodynamic therapy |
US20040266748A1 (en) | 2001-10-03 | 2004-12-30 | Robinson Byron C | Photosensitizing carbamate derivatives |
DE10154436A1 (de) | 2001-11-07 | 2003-05-15 | Rodotech Gmbh | pyro-Bakteriopheophorbidderivate |
GB0130778D0 (en) | 2001-12-21 | 2002-02-06 | Catalyst Biomedica Ltd | Novel compounds |
EP1509129A4 (en) | 2002-05-08 | 2009-03-25 | Yeda Res & Dev | SENSITIZED ONLINE BOLD NUCLEAR PENNOMOGRAPHY PROCESS |
DE60328496D1 (en) * | 2002-06-27 | 2009-09-03 | Health Research Inc | Fluorinierte chlorin und bacteriochlorin photosensitizer für fotodynamische therapie |
IL152900A0 (en) | 2002-11-17 | 2003-06-24 | Yeda Res & Dev | Water-soluble bacteriochlorophyll derivatives and their pharmaceutical uses |
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