HRP20160079T1 - Postupak industrijskog pročišćavanja biološki aktivnih fikotoksina - Google Patents
Postupak industrijskog pročišćavanja biološki aktivnih fikotoksina Download PDFInfo
- Publication number
- HRP20160079T1 HRP20160079T1 HRP20160079TT HRP20160079T HRP20160079T1 HR P20160079 T1 HRP20160079 T1 HR P20160079T1 HR P20160079T T HRP20160079T T HR P20160079TT HR P20160079 T HRP20160079 T HR P20160079T HR P20160079 T1 HRP20160079 T1 HR P20160079T1
- Authority
- HR
- Croatia
- Prior art keywords
- solution
- phycotoxins
- volume
- extraction
- eluate
- Prior art date
Links
- 231100000769 Phycotoxin Toxicity 0.000 title claims 9
- 238000000034 method Methods 0.000 title claims 9
- 238000000746 purification Methods 0.000 title claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 6
- 238000010828 elution Methods 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 239000008346 aqueous phase Substances 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000008187 granular material Substances 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- 241000192700 Cyanobacteria Species 0.000 claims 2
- 239000005909 Kieselgur Substances 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 239000012141 concentrate Substances 0.000 claims 2
- 230000009089 cytolysis Effects 0.000 claims 2
- 230000007717 exclusion Effects 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 239000006228 supernatant Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- 241000192542 Anabaena Species 0.000 claims 1
- 241000192660 Aphanizomenon Species 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 241001299740 Cylindrospermopsis Species 0.000 claims 1
- 241000761673 Gomphosphaeria Species 0.000 claims 1
- 241000192701 Microcystis Species 0.000 claims 1
- 241001181287 Microseira wollei Species 0.000 claims 1
- PPEKGEBBBBNZKS-UHFFFAOYSA-N Neosaxitoxin Natural products N=C1N(O)C(COC(=O)N)C2N=C(N)NC22C(O)(O)CCN21 PPEKGEBBBBNZKS-UHFFFAOYSA-N 0.000 claims 1
- 241000192497 Oscillatoria Species 0.000 claims 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims 1
- 238000005349 anion exchange Methods 0.000 claims 1
- 239000011324 bead Substances 0.000 claims 1
- 238000005341 cation exchange Methods 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 238000011210 chromatographic step Methods 0.000 claims 1
- 239000012153 distilled water Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 239000001963 growth medium Substances 0.000 claims 1
- 238000000265 homogenisation Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- PPEKGEBBBBNZKS-HGRQIUPRSA-N neosaxitoxin Chemical compound N=C1N(O)[C@@H](COC(=O)N)[C@@H]2NC(=N)N[C@@]22C(O)(O)CCN21 PPEKGEBBBBNZKS-HGRQIUPRSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- 238000002953 preparative HPLC Methods 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- RPQXVSUAYFXFJA-HGRQIUPRSA-N saxitoxin Chemical compound NC(=O)OC[C@@H]1N=C(N)N2CCC(O)(O)[C@@]22N=C(N)N[C@@H]12 RPQXVSUAYFXFJA-HGRQIUPRSA-N 0.000 claims 1
- RPQXVSUAYFXFJA-UHFFFAOYSA-N saxitoxin hydrate Natural products NC(=O)OCC1N=C(N)N2CCC(O)(O)C22NC(N)=NC12 RPQXVSUAYFXFJA-UHFFFAOYSA-N 0.000 claims 1
- 238000000638 solvent extraction Methods 0.000 claims 1
Classifications
-
- 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
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
-
- 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
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Cosmetics (AREA)
- Cephalosporin Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Claims (7)
1. Postupak industrijskog pročišćavanja biološki aktivnih fikotoksina neosaksitoksina, saksitoksina i gonijaulatoksina iz cijanobakterija, taj postupak obuhvaća korake:
a) nabava izvora fikotoksina, točnije klonova cijanobakterijske kulture, koji se razdvajaju u medij kulture i vlažnu granulu cijanobakterijske stanice ili smrznutu granulu cijanobakterijske stanice;
b) ta granula se lizira putem homogenizacije, ekstrakcije otapalom, kuglastog mlina (bead mill), ciklusima smrzavanja/odmrzavanja, ultrazvučno ili enzimatskom lizom;
c) materijal iz lize cijanobakterijskih stanica dobiven u koraku b) podvrgava se hladnoj ekstrakciji i razdvajanju organskih / vodenih faza, točnije smjesi 50% volumena 1:1 kloroform:metanol i 50% volumena 1 mM octene kiseline, na pH između 4 i 5, i nakon čega slijedi razdvajanje organskih i vodenih faza uporabom kloroform:metanol 1:1 po volumenu, što se ponavlja između 1 i 5 puta;
d) dobivanje koncentrata vodene faze dobivene u koraku (c);
e) centrifugiranje koncentrata dobivenog u koraku d) da se dobije supernatant;
f) puštanje supernatanta kroz kolonu dijatomejske zemlje, i ispiranje kolone otopinom za ispiranje; zatim dobivanje fikotoksinskog eluata s otopinom za eluaciju;
g) eluat iz prethodnog koraka se propušta kroz kolone aktivnog ugljena, i te se kolone aktivnog ugljena zatim ispiru destiliranom vodom da se uklone zadržani pigmenti i onečišćenja; fikotoksini se eluiraju s otopinom za eluaciju;
h) eluat iz prethodnog koraka se propušta ponovno kroz kolonu dijatomejske zemlje; kolone se ispiru otopinom kao u koraku f), i fikotoksini se eluiraju ekstrakcijskom otopinom;
i) eluat iz prethodnog koraka se ostavlja u vodenoj fazi uz isparavanje organskih otapala da se dobije djelomično pročišćeni fikotoksinski ekstrakt;
j) djelomično pročišćeni ekstrakt iz prethodnog koraka podvrgava se preparativnoj tekućinskoj kromatografiji visoke učinkovitosti u nekoliko koraka da se dobije čisti biološki aktivni fikotoksin.
2. Postupak prema zahtjevu 1, u kojem se ekstrakcija u koraku (c) ponavlja 3 puta.
3. Postupak prema zahtjevu 1, u kojem je otopina za ispiranje u koracima f) i h) 50 mM octena kiselina, u koraku (f) kolone se ispiru volumenom koji je 5 do 15 puta veći od volumena kolone i otopina za eluaciju je alkoholna ekstrakcijska smjesa.
4. Postupak prema zahtjevu 1, u kojem je otopina za eluaciju u koraku g) alkoholna smjesa za eluaciju.
5. Postupak prema zahtjevu 1, u kojem je otopina u koraku h) smjesa 1:1:1 vol/vol/vol kloroform:metanol:voda.
6. Postupak prema zahtjevu 1, u kojem su kromatografski koraci u koraku j) redom isključivanje po veličini, izmjena aniona, izmjena kationa i isključivanje po veličini.
7. Postupak prema bilo kojem od zahtjeva 1 do 6, u kojem cijanobakterije mogu proizvesti fikotoksine koji pripadaju rodovima Cylindrospermopsis sp, Microcystis sp, Anabaena sp, Gomphosphaeria sp, Oscillatoria sp, Aphanizomenon sp i Lyngbya wollei.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CL2009000723A CL2009000723A1 (es) | 2009-03-24 | 2009-03-24 | Metodo de purificacion industrial de ficotoxinas biologicamente activas que comprende proporcionar una cantidad adecuada de una fuente de ficotoxinas como por ejemplo el cultivo de un clon de cianobacterias. |
| PCT/IB2010/051187 WO2010109386A1 (es) | 2009-03-24 | 2010-03-18 | Método de purificación industrial de ficotoxinas biológicamente activas |
| EP10755518.7A EP2412714B9 (en) | 2009-03-24 | 2010-03-18 | Method for the industrial purification of biologically active phycotoxins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20160079T1 true HRP20160079T1 (hr) | 2016-04-08 |
Family
ID=42780210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20160079TT HRP20160079T1 (hr) | 2009-03-24 | 2016-01-25 | Postupak industrijskog pročišćavanja biološki aktivnih fikotoksina |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP2412714B9 (hr) |
| JP (1) | JP5728774B2 (hr) |
| KR (1) | KR20110130420A (hr) |
| AR (1) | AR075931A1 (hr) |
| BR (1) | BRPI1013548B8 (hr) |
| CA (1) | CA2754154C (hr) |
| CL (1) | CL2009000723A1 (hr) |
| DK (1) | DK2412714T5 (hr) |
| ES (1) | ES2562637T3 (hr) |
| HR (1) | HRP20160079T1 (hr) |
| HU (1) | HUE027480T2 (hr) |
| MX (1) | MX2011010005A (hr) |
| PE (1) | PE20110903A1 (hr) |
| WO (1) | WO2010109386A1 (hr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8957207B2 (en) | 2009-03-24 | 2015-02-17 | Proteus S.A. | Methods for producing phycotoxins |
| EP3492075B1 (en) | 2013-03-15 | 2023-12-13 | The Children's Medical Center Corporation | Neosaxitoxin combination formulations for prolonged local anesthesia |
| US9902625B2 (en) | 2014-09-03 | 2018-02-27 | International Business Machines Corporation | Removal of HAB-produced toxins from bodies of water |
| GB201602576D0 (en) | 2016-02-12 | 2016-03-30 | Bergen Teknologioverforing As | Process |
| CN107602580B (zh) * | 2017-09-08 | 2019-06-11 | 浙江理工大学 | 一种聚酮类化合物及其制备方法和应用 |
| CN109142595A (zh) * | 2018-08-23 | 2019-01-04 | 中国水产科学研究院黄海水产研究所 | 一种麻痹性贝类毒素标准溶液的制备方法 |
| WO2020058750A1 (en) * | 2018-09-21 | 2020-03-26 | The Cawthron Institute Trust Board | A semisynthetic method of preparing neosaxitoxin |
| CN117964629A (zh) * | 2018-09-21 | 2024-05-03 | 考思隆研究所托管委员会 | 将膝沟藻毒素制备性规模转化为新石房蛤毒素 |
| CN114657222A (zh) * | 2022-04-08 | 2022-06-24 | 湖北省水利水电科学研究院 | 一种从水华束丝藻中提取类菌胞素氨基酸的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001413A (en) | 1973-06-12 | 1977-01-04 | Astra Pharmaceutical Products, Inc. | Pharmaceutical local anesthetic composition employing saxitoxin |
| AU6883798A (en) * | 1997-04-02 | 1998-10-22 | Regents Of The University Of California, The | Method of anesthesia |
| CA2466697C (en) * | 2001-11-15 | 2013-09-24 | Micro Algae Corporation | Pharmaceutical compositions containing 3,4-propinoperhydropurines and uses thereof for blocking neuronal transmission |
| CA2821239C (en) * | 2004-05-07 | 2016-04-12 | Phytotox Limited | Phycotoxins and uses thereof |
| DE102006028817A1 (de) * | 2006-06-21 | 2007-12-27 | Evonik Degussa Gmbh | Aufarbeitung von Reaktionslösungen aus Ganzzell-Biotransformationen |
-
2009
- 2009-03-24 CL CL2009000723A patent/CL2009000723A1/es unknown
-
2010
- 2010-03-18 KR KR1020117021288A patent/KR20110130420A/ko active Search and Examination
- 2010-03-18 BR BRPI1013548A patent/BRPI1013548B8/pt active IP Right Grant
- 2010-03-18 DK DK10755518.7T patent/DK2412714T5/en active
- 2010-03-18 WO PCT/IB2010/051187 patent/WO2010109386A1/es active Application Filing
- 2010-03-18 PE PE2011001285A patent/PE20110903A1/es active IP Right Grant
- 2010-03-18 JP JP2012501444A patent/JP5728774B2/ja active Active
- 2010-03-18 EP EP10755518.7A patent/EP2412714B9/en active Active
- 2010-03-18 CA CA2754154A patent/CA2754154C/en active Active
- 2010-03-18 ES ES10755518.7T patent/ES2562637T3/es active Active
- 2010-03-18 HU HUE10755518A patent/HUE027480T2/en unknown
- 2010-03-18 MX MX2011010005A patent/MX2011010005A/es active IP Right Grant
- 2010-03-23 AR ARP100100934A patent/AR075931A1/es active IP Right Grant
-
2016
- 2016-01-25 HR HRP20160079TT patent/HRP20160079T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUE027480T2 (en) | 2016-09-28 |
| DK2412714T3 (en) | 2016-02-01 |
| CA2754154A1 (en) | 2010-09-30 |
| EP2412714B1 (en) | 2015-11-11 |
| CL2009000723A1 (es) | 2009-06-19 |
| CA2754154C (en) | 2013-12-17 |
| ES2562637T3 (es) | 2016-03-07 |
| AR075931A1 (es) | 2011-05-04 |
| BRPI1013548B8 (pt) | 2021-05-25 |
| MX2011010005A (es) | 2011-10-10 |
| DK2412714T5 (en) | 2017-02-27 |
| PE20110903A1 (es) | 2012-01-19 |
| JP5728774B2 (ja) | 2015-06-03 |
| ES2562637T9 (es) | 2017-05-30 |
| BRPI1013548B1 (pt) | 2020-06-09 |
| EP2412714B9 (en) | 2016-11-23 |
| BRPI1013548A2 (pt) | 2016-09-20 |
| EP2412714A4 (en) | 2012-10-10 |
| WO2010109386A1 (es) | 2010-09-30 |
| EP2412714A1 (en) | 2012-02-01 |
| JP2012521408A (ja) | 2012-09-13 |
| KR20110130420A (ko) | 2011-12-05 |
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