PL231816B1 - 1'Palmitoyl-2'-(3,7-Dimethyl-3-vinylocta-6-enyl)-sn-glycero-3'-phosphocholine and method for obtaining it - Google Patents
1'Palmitoyl-2'-(3,7-Dimethyl-3-vinylocta-6-enyl)-sn-glycero-3'-phosphocholine and method for obtaining itInfo
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- PL231816B1 PL231816B1 PL418945A PL41894516A PL231816B1 PL 231816 B1 PL231816 B1 PL 231816B1 PL 418945 A PL418945 A PL 418945A PL 41894516 A PL41894516 A PL 41894516A PL 231816 B1 PL231816 B1 PL 231816B1
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- dimethyl
- vinylocta
- phosphocholine
- palmitoyl
- glycero
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Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 1’-palmitoilo-2’-(3,7-dimetylo-3-winylokta-6-enylo)-sn-glicero-3’-fosfocholina o wzorze 1, przedstawionym na rysunku.The subject of the invention is 1'-palmitoyl-2 '- (3,7-dimethyl-3-vinylocta-6-enyl) -sn-glycero-3'-phosphocholine of the formula 1, shown in the drawing.
Przedmiotem wynalazku jest także sposób otrzymywania 1 ’-palmitoilo-2’-(3,7-dimetylo-3-winylokta-6-enylo)-sn-glicero-3'-fosfocholiny o wzorze 1.The invention also relates to a method for the preparation of 1 '-palmitoyl-2' - (3,7-dimethyl-3-vinylocta-6-enyl) -sn-glycero-3'-phosphocholine of formula 1.
Związek ten może znaleźć zastosowanie w przemyśle farmaceutycznym jako prolek w terapii chorób nowotworowych.This compound may find application in the pharmaceutical industry as a prodrug in the treatment of neoplastic diseases.
Dotychczas znana jest fosfatydylocholina zawierająca cząsteczkę kwasu palmitynowego w pozycji sn-1 i resztę kwasu geranylowego w pozycji sn-2, która posiada udokumentowaną aktywność cytotoksyczną względem komórek nowotworowych białaczki linii MV4-11 (Gliszczyńska A i in., PlosOne, 11(6), e0157278).So far, phosphatidylcholine containing a palmitic acid molecule in the sn-1 position and a geranylic acid residue in the sn-2 position, which has a documented cytotoxic activity against the neoplastic cells of the MV4-11 leukemia line, is known (Gliszczyńska A et al., PlosOne, 11 (6), e0157278).
Kwas 3,7-dimetylo-3-winylookta-6-enowy jest rozgałęzionym analogiem strukturalnym kwasu geranylowego, który przy atomie węgla C-3 łańcucha izoprenoidowego posiada ugrupowanie winylowe.3,7-dimethyl-3-vinylocta-6-enoic acid is a branched structural analog of geranylic acid which has a vinyl moiety at the C-3 carbon of the isoprenoid chain.
Z opisu zgłoszenia wynalazku P.418652 znana jest fosfatydylocholina zawierająca dwie cząsteczki kwasu 3,7-dimetylo-3-winylookta-6-enowego jednocześnie w pozycji sn-1 i sn-2 fosfatydylocholiny. Nie jest znana w literaturze fosfatydylocholina zawierająca cząsteczkę kwasu palmitynowego w pozycji sn-1 i cząsteczkę kwasu 3,7-dimetylo-3-winylookta-6-enowego w pozycji sn-2.From the description of the invention application P.418652 there is known phosphatidylcholine containing two 3,7-dimethyl-3-vinylocta-6-enoic acid molecules simultaneously in the sn-1 and sn-2 positions of phosphatidylcholine. It is not known in the literature that phosphatidylcholine contains a palmitic acid molecule in the sn-1 position and a 3,7-dimethyl-3-vinylocta-6-enoic acid molecule in the sn-2 position.
Istotą wynalazku jest fosfolipidowa pochodna, którą jest 1’-palmitoilo-2’-(3,7-dimetylo-3-winylokta-6-enylo)-sn-glicero-3'-fosfocholina, zawierająca kwas palmitynowy w pozycji sn-1 oraz kwas 3,7-dimetylo-3-winylookta-6-enowy w pozycji sn-2.The essence of the invention is a phospholipid derivative, which is 1'-palmitoyl-2 '- (3,7-dimethyl-3-vinylocta-6-enyl) -sn-glycero-3'-phosphocholine, containing palmitic acid in the sn-1 position and 3,7-dimethyl-3-vinylocta-6-enoic acid at the sn-2 position.
Istota sposobu, według wynalazku polega na tym, że do mieszaniny 1-palmitoilo-sn-glicero-3-fosfocholiny, kwasu 3,7-dimetylo-3-winylookta-6-enowego i 4-dimetyloaminopirydyny rozpuszczonych w bezwodnym chlorku metylenu albo chloroformie, dodaje się WW-dicykloheksylokarbodiimid rozpuszczony w jednym z wyżej wymienionych rozpuszczalników, po czym całość miesza się przez co najmniej 1 dobę, a następnie wydziela powstały produkt 1 ’-palmitoilo-2’-(3,7-dimetylo-3-winylokta-6-enylo)-sn-glicero-3’-fosfocholinę.The essence of the method according to the invention consists in the fact that a mixture of 1-palmitoyl-sn-glycero-3-phosphocholine, 3,7-dimethyl-3-vinylocta-6-enoic acid and 4-dimethylaminopyridine dissolved in anhydrous methylene chloride or chloroform, WW-dicyclohexylcarbodiimide dissolved in one of the above-mentioned solvents is added, followed by stirring for at least 1 day, and then isolating the resulting product 1'-palmitoyl-2 '- (3,7-dimethyl-3-vinylocta-6- enyl) -sn-glycero-3'-phosphocholine.
Korzystnie jest, gdy proces estryfikacji prowadzi się w temperaturze od 18 do 55°C.Preferably, the esterification process is carried out at a temperature of 18 to 55 ° C.
Korzystnie jest, gdy jako rozpuszczalnik w reakcji estryfikacji stosuje się bezwodny chlorek metylenu lub bezwodny chloroform.Preferably, anhydrous methylene chloride or anhydrous chloroform is used as the esterification solvent.
Zasadniczą zaletą wynalazku jest otrzymanie z dużą wydajnością i wysoką czystością 1 '-palmitoilo-2’-(3,7-dimetylo-3-winylokta-6-enylo)-sn-glicero-3’-fosfocholiny o wzorze 1.The main advantage of the invention is the preparation of 1'-palmitoyl-2 '- (3,7-dimethyl-3-vinylocta-6-enyl) -sn-glycero-3'-phosphocholine of formula 1 with high yield and high purity.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an embodiment.
P r z y k ł a d 1.P r z k ł a d 1.
Do roztworu osuszonej 1-palmitoilo-sn-glicero-3-fosfocholiny (150 mg, 0.302 mmol) rozpuszczonej w bezwodnym chlorku metylenu (CH2CI2, 1 cm3) dodaje się kwas 3,7-dimetylo-3-winylookta-6-enowego (119 mg, 604 mmol), 4-dimetyloaminopirydynę (DMAP) (74 mg, 0.604 mmol) rozpuszczoną w 3 cm3 bezwodnego chlorku metylenu oraz W,W-dicykloheksylokarbodiimidu (DCC) (268 mg, 1.3 mmol) rozpuszczonego również w 5 cm3 bezwodnego chlorku metylenu. Zawiesinę miesza się intensywnie w temperaturze 40°C w atmosferze N2 przez 72 godziny. Po tym czasie mieszaninę poreakcyjną odsącza się pod zmniejszonym ciśnieniem na lejku Schotta, a do przesączu dodaje się żywicę jonowymienną (DOWEX 50W X8 w formie H+) i miesza przez 30 minut. Następnie żywicę jonowymienną odsącza się, a rozpuszczalnik odparowuje się pod zmniejszonym ciśnieniem. Surowy produkt oczyszcza się za pomocą chromatografii kolumnowej na żelu krzemionkowym stosując jako eluent mieszaninę rozpuszczalników CHCb:MeOH:H2O, 65:25:4 (v/v/v). Otrzymuje się 118 mg (0.176 mmol) 1'-palmitoilo-2’-(3,7-dimetylo-3-winylokta-6-enylo)-sn-glicero-3’-fosfocholiny z wydajnością 58% w postaci mazistej substancji o czystości >99% (wg HPLC).To a dried solution of 1-palmitoyl-sn-glycero-3-phosphocholine (150 mg, 0.302 mmol) dissolved in dry methylene chloride (CH2Cl2, 1 cm 3) was added acid 3,7-dimethyl-3-winylookta-6-enoic acid ( 119 mg, 604 mmol), 4-dimethylaminopyridine (DMAP) (74 mg, 0.604 mmol) dissolved in 3 cm 3 of dry methylene chloride and N, N- dicyclohexylcarbodiimide (DCC) (268 mg, 1.3 mmol) dissolved also in 5 cm 3 anhydrous methylene chloride. The suspension is stirred vigorously at 40 ° C under N2 for 72 hours. After this time, the reaction mixture was filtered under reduced pressure on a Schott funnel, and an ion exchange resin (DOWEX 50W X8 in H + form) was added to the filtrate and stirred for 30 minutes. The ion exchange resin is then filtered off and the solvent is evaporated off under reduced pressure. The crude product was purified by column chromatography on silica gel using a solvent mixture of CHCl2: MeOH: H2O 65: 25: 4 (v / v / v) as the eluent. 118 mg (0.176 mmol) of 1'-palmitoyl-2 '- (3,7-dimethyl-3-vinylocta-6-enyl) -sn-glycero-3'-phosphocholine are obtained with a yield of 58% in the form of a greasy substance of purity > 99% (by HPLC).
Dane spektroskopowe otrzymanego związku są następujące:The spectroscopic data of the obtained compound are as follows:
1H NMR (600 MHz, CDCI3/CD3OD 2:1 (v/v)), δ: 0.62 (t, J = 7.2 Hz, 6H, CH3(CH2)14C(O) (A), CH3(CH2)14C(O) (B)), 0.88 (s, 6H, CH3-11 (A), CH3-11 (B)), 1.00-1.03 (m, 48H, CH3(CH2)12CH2CH2C(O) (A), CH3(CH2)12CH2CH2C(O) (B)), 1.15 (m, 4H, CH2-4 (A), CH2-4 (B)), 1.32, 1.40 (dwa s, 12H, CH3-8 (A), CH3-8 (B), CH3-12 (A), CH3-12 (B)), 1.33-1.36 (m, 4H, CH3(CH2)13CH2CH2C(O) (A), CH3(CH2)13CH2CH2C(O) (B)), 1.65 (m, 4H, CH2-5 (A), CH2-5 (B)), 2.05 (t, J = 7.8 Hz, 4H, CH3(CH2)13CH2C(O) (A), CH3(CH2)13CH2C(O) (B)), 2.07-2.14 (cztery d, J = 13.2 Hz, dwa układy AB, 4H, CH2-2 (A), CH2-2 (B)), 2.96 (s, 18H, -N(CH3)3 (A), -N(CH3)3 (B)), 3.35 (m, 4H, CH2-3 (A), CH2-3 (B)), 3.69-3.73 (m, 4H, CH2-3' (A), CH2-3' (B)), 3.87 (m, 2H, jeden z CH2-1' (A), jeden z CH2-1' (B)), 3.99 (m, 4H, CH2-a (A), CH2-a (B)), 4.14 (m, 2H, jeden z CH2-1’ (A), jeden z CH2-1’ (B)), 4.68-4.72 (dwa d, J = 17.4, 2H, jeden z CH2-10 (A), jeden z CH2-10 (B)), 4.77-4.79 (dwa d, J = 10.8 Hz, 2H, jeden 1 H NMR (600 MHz, CDCl3 / CD3OD 2: 1 (v / v)) δ: 0.62 (t, J = 7.2 Hz, 6H, CH3 (CH2) 14C (O) (A) CH3 (CH2) 14C (O) (B)), 0.88 (s, 6H, CH3-11 (A), CH3-11 (B)), 1.00-1.03 (m, 48H, CH3 (CH2) 12CH2CH2C (O) (A), CH3 (CH2) 12CH2CH2C (O) (B)), 1.15 (m, 4H, CH2-4 (A), CH2-4 (B)), 1.32, 1.40 (two s, 12H, CH3-8 (A), CH3 -8 (B), CH3-12 (A), CH3-12 (B)), 1.33-1.36 (m, 4H, CH3 (CH2) 13CH2CH2C (O) (A), CH3 (CH2) 13CH2CH2C (O) ( B)), 1.65 (m, 4H, CH2-5 (A), CH2-5 (B)), 2.05 (t, J = 7.8 Hz, 4H, CH3 (CH2) 13CH2C (O) (A), CH3 ( CH2) 13CH2C (O) (B)), 2.07-2.14 (four d, J = 13.2 Hz, two AB circuits, 4H, CH2-2 (A), CH2-2 (B)), 2.96 (s, 18H, -N (CH3) 3 (A), -N (CH3) 3 (B)), 3.35 (m, 4H, CH2-3 (A), CH2-3 (B)), 3.69-3.73 (m, 4H, CH2-3 '(A), CH2-3' (B)), 3.87 (m, 2H, one of CH2-1 '(A), one of CH2-1' (B)), 3.99 (m, 4H, CH2-a (A), CH2-a (B)), 4.14 (m, 2H, one from CH2-1 '(A), one from CH2-1' (B)), 4.68-4.72 (two d, J = 17.4, 2H, one from CH2-10 (A), one from CH2-10 (B)), 4.77-4.79 (two d, J = 10.8 Hz, 2H, one
PL 231 816 B1 z CH2-10 (A), jeden z CH2-IO (B)), 4.78-4.80 (m, 2H, H-6 (A), H-6 (B)), 4.94-4.97 (m, 2H, H-2' (A), H-2' (B)), 5.52-5.57 (dwa dd, J = 17.4, 10.8 Hz, 2H, H-9 (A), H-9 (B));PL 231 816 B1 of CH2-10 (A), one of CH2-IO (B)), 4.78-4.80 (m, 2H, H-6 (A), H-6 (B)), 4.94-4.97 (m , 2H, H-2 '(A), H-2' (B)), 5.52-5.57 (two dd, J = 17.4, 10.8 Hz, 2H, H-9 (A), H-9 (B)) ;
13C NMR (151 MHz, CDCI3/CD3OD 2:1 (v/v)) δ: 13.37 (CH3(CH2)14C(O) (A), (CH3(CH2)14C(O) (B)), 16.85, 24.91 (C-8 (A), C-8 (B), C-12 (A), C-12 (B)), 22.15 (CH3CH2(CH2)13C(O) (A), CH3CH2(CH2)13C(O) (B)), 22.33, 22.35 (C-5 (A), C-5 (B)), 22.43, 22.47 (C-11 (A), C-11 (B)), 24.33 (CH3(CH2)12CH2CH2C(O) (A) , CH3(CH2)12CH2CH2C(O) (B)), 28.64, 28.78, 28.84, 28.98, 29.11, 29.13, 29.16, 31.42 (CH3CH2(CH2)hCH2CH2C(O) (A), CH3CH2(CH2)nCH2CH2C(O) (B)), 33.57 (CH3(CH2)13CH2C(O) (A), CH3(CH2)13CH2C(O) (B)), 38.73, 38.75 (C-3 (A), C-3 (B)), 40.21,40.22 (C-4 (A), C-4 (B)), 44.38, 44.43 (C-2 (A), C-2 (B)), 53.56 (t, J = 3.6 Hz, -N(CH3)3 (A), -N(CH3)3 (B)), 58.59 (d, J = 4.9 Hz, C-α (A), C-a (B) ), 62.39, 62.40 (C-1' (A), C-1' (B)), 63.04 (d, J = 5.1 Hz (C-3' (A)), 63.07 (d, J = 5.3 Hz, (C-3' (B)), 65.98 (m, C-β (A), C-β (B)), 69.88 (d, J = 8.0 Hz, C-2' (A), C-2' (B)), 111.75 (C-10 (A), C-10 (B)), 123.80 (C-6 (A), C-6 (B)), 130.92 (C-7 (A), C-7 (B)), 144.73, 144.76 (C-9 (A), C-9 (B)), 170.95 (C-1 (A), C-1 (B)), 173.59 (CH3(CH2)13CH2C(O) (A), CH3(CH2)13CH2C(O) (B)); 13 C NMR (151 MHz, CDCl3 / CD3OD 2: 1 (v / v)) δ: 13.37 (CH3 (CH2) 14C (O) (A), (CH3 (CH2) 14C (O) (B)), 16.85 , 24.91 (C-8 (A), C-8 (B), C-12 (A), C-12 (B)), 22.15 (CH3CH2 (CH2) 13C (O) (A), CH3CH2 (CH2) 13C (O) (B)), 22.33, 22.35 (C-5 (A), C-5 (B)), 22.43, 22.47 (C-11 (A), C-11 (B)), 24.33 (CH3 (CH2) 12CH2CH2C (O) (A), CH3 (CH2) 12CH2CH2C (O) (B)), 28.64, 28.78, 28.84, 28.98, 29.11, 29.13, 29.16, 31.42 (CH3CH2 (CH2) hCH2CH2C (O) (A ), CH3CH2 (CH2) nCH2CH2C (O) (B)), 33.57 (CH3 (CH2) 13CH2C (O) (A), CH3 (CH2) 13CH2C (O) (B)), 38.73, 38.75 (C-3 ( A), C-3 (B)), 40.21,40.22 (C-4 (A), C-4 (B)), 44.38, 44.43 (C-2 (A), C-2 (B)), 53.56 (t, J = 3.6 Hz, -N (CH3) 3 (A), -N (CH3) 3 (B)), 58.59 (d, J = 4.9 Hz, C-α (A), Ca (B)) , 62.39, 62.40 (C-1 '(A), C-1' (B)), 63.04 (d, J = 5.1 Hz (C-3 '(A)), 63.07 (d, J = 5.3 Hz, ( C-3 '(B)), 65.98 (m, C-β (A), C-β (B)), 69.88 (d, J = 8.0 Hz, C-2' (A), C-2 '( B)), 111.75 (C-10 (A), C-10 (B)), 123.80 (C-6 (A), C-6 (B)), 130.92 (C-7 (A), C-7 (B)), 144.73, 144.76 (C-9 (A), C-9 (B)), 170.95 (C-1 (A), C-1 (B)), 173.59 (CH3 (CH2) 13CH2C (O) (A), CH3 (CH2) 13CH2C (O) (B));
31P NMR (243 MHz, CDCb/CD3OD 2:1 (v/v)) δ: -0.80; 31 P NMR (243 MHz, CDCb / CD3OD 2: 1 (v / v)) δ: -0.80;
(a, β) - oznacza sygnały pochodzące od choliny(a, β) - indicates choline-derived signals
P r z y k ł a d 2.P r z k ł a d 2.
Postępuje się tak jak w przykładzie 1, z tym, że jako rozpuszczalnik w reakcji estryfikacji stosuje się bezwodny chloroform. Otrzymuje się 114 mg 1'-palmitoilo-2'-(3,7-dimetylo-3-winylokta-6-enylo)-snglicero-3'-fosfocholiny z wydajnością 56% w postaci mazistej substancji o czystości >99% (wg HPLC).The procedure is as in Example 1, except that anhydrous chloroform is used as the esterification solvent. 114 mg of 1'-palmitoyl-2 '- (3,7-dimethyl-3-vinylocta-6-enyl) -snglycero-3'-phosphocholine are obtained with a yield of 56% as a greasy substance> 99% pure (according to HPLC ).
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