ES2554853T3 - Miméticos de la apolipoproteína A-I - Google Patents
Miméticos de la apolipoproteína A-I Download PDFInfo
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- ES2554853T3 ES2554853T3 ES10741801.4T ES10741801T ES2554853T3 ES 2554853 T3 ES2554853 T3 ES 2554853T3 ES 10741801 T ES10741801 T ES 10741801T ES 2554853 T3 ES2554853 T3 ES 2554853T3
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- 102000005666 Apolipoprotein A-I Human genes 0.000 title description 4
- 108010059886 Apolipoprotein A-I Proteins 0.000 title description 4
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 29
- 150000003839 salts Chemical class 0.000 abstract description 7
- 125000000539 amino acid group Chemical group 0.000 description 39
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 150000008575 L-amino acids Chemical group 0.000 description 5
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 5
- 125000003275 alpha amino acid group Chemical group 0.000 description 5
- 150000008574 D-amino acids Chemical group 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- DCXYFEDJOCDNAF-UWTATZPHSA-N D-Asparagine Chemical group OC(=O)[C@H](N)CC(N)=O DCXYFEDJOCDNAF-UWTATZPHSA-N 0.000 description 3
- ZDXPYRJPNDTMRX-GSVOUGTGSA-N D-glutamine Chemical group OC(=O)[C@H](N)CCC(N)=O ZDXPYRJPNDTMRX-GSVOUGTGSA-N 0.000 description 3
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 3
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 3
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical group OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 3
- -1 Phe Chemical compound 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N Arginine Chemical compound OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical compound CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N Cysteine Chemical compound SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 description 1
- 244000191761 Sida cordifolia Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/775—Apolipopeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/1703—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- A61K38/1709—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K38/00—Medicinal preparations containing peptides
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- General Chemical & Material Sciences (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
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Abstract
Péptido o sal farmacéuticamente aceptable del mismo, en el que el péptido es: Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Inp (SEQ. ID. NO. 16).
Description
y
5
10
en las que n es un número entero de 1 a 4. En una realización, el residuo de aminoácido aromático es un residuo de L-aminoácido. En otra realización, el residuo de aminoácido aromático es un residuo de D-aminoácido. En otra
15 realización, el residuo de aminoácido aromático es un residuo de aminoácido aquiral.
[0043] Las clasificaciones de los residuos de aminoácidos codificados genéticamente y no codificados genéticamente de acuerdo con las categorías definidas anteriormente se resumen en la siguiente tabla. Debe entenderse que la siguiente tabla se incluye sólo con fines ilustrativos y no pretende ser una lista exhaustiva de
20 residuos de aminoácidos que se puede utilizar en los miméticos de ApoA-I descritos en este documento. Otros residuos de aminoácidos no divulgados específicamente en este documento pueden clasificarse fácilmente en base a sus propiedades físicas y químicas observadas en vista de las definiciones proporcionadas en el presente documento. Algunas clasificaciones de residuos de aminoácidos se incluyen en la tabla 2 a continuación.
25 Tabla 2.
- Clasificaciones de algunos residuos de aminoácido
- Clasificación
- Codificado genéticamente No codificado genéticamente
- Hidrófobo
- Aromático
- F, Y, W PhG, NaI, Thi, Tic, Phe(4-Cl), Phe(2-F), Phe(3-F), Phe(4-F), hPhe
- No polar
- L, V, I, M, G, A, P -Ala, t-BuA, t-BuG, Melle, Nle, MeVal, ChA, MeGly, Aib, Nip, hPro
- Alifático
- A, V, L, I, P -Ala, Aib, t-BuA, t-BuG, Melle, ChA, Nle, MeVal, Nip, hPro, Inp, azPro, Pip,
- Hidrófilo
- Ácido
- D, E
- Básico
- H, K, R Dpr, Orn, hArg, Phe(p-NH2), Dbu, Dab, hArg
- Polar
- C, Q, N, S, T Cit, Pen, AcLys, MSO, bAla, hSer, hCys, hSer, Hyp
- Rotura de hélice
- P, G MeGly, L-aminoácidos (en Dpéptidos), D-Pro y otros Daminoácidos (en L-péptidos)
[0044] Como se entenderá por los expertos en la técnica, las clasificaciones definidas anteriormente no son mutuamente excluyentes. De este modo, los residuos de aminoácido que tienen cadenas laterales que muestran dos 30 o más propiedades físico-químicas pueden incluirse en múltiples categorías. Por ejemplo, las cadenas laterales de aminoácidos que tienen grupos aromáticos que están sustituidos adicionalmente con sustituyentes polares, tales como Tyr (Y) o su correspondiente D-enantiómero, pueden mostrar tanto propiedades hidrófobas aromáticas como propiedades polares o hidrófilas, y por lo tanto pueden incluirse tanto en la categoría de aromáticos como de polares. La clasificación apropiada de cualquier residuo de aminoácido será evidente para los expertos en la técnica,
35 especialmente en vista de la descripción proporcionada en el presente documento.
[0045] Además, el residuo de aminoácido Cys (C) o su D-enantiómero correspondiente pueden formar puentes disulfuro con otros residuos de Cys (C) o sus correspondientes D-enantiómeros o con otros aminoácidos que contienen sulfanilo. La capacidad de los residuos de Cys (C) (y otros aminoácidos con cadenas laterales que 40 contienen -SH) de existir en un péptido tanto en forma reducida de -SH libre como en forma oxidada de puentes disulfuro afecta a si los residuos de Cys (C) o sus correspondiente D-enantiómeros contribuyen al carácter neto hidrófobo o hidrófilo de un péptido. Aunque la Cys (C) o su correspondiente D-enantiómero muestran una hidrofobicidad de 0,29 según la escala consenso normalizada de Eisenberg (Eisenberg, 1984, supra), debe entenderse que para los objetivos de la presente invención Cys (C) y su correspondiente D-enantiómero se
45 clasifican como aminoácidos hidrófilos polares, a pesar de las clasificaciones generales definidas anteriormente.
14 5
15
25
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II. Miméticos de ApoA-I
[0046] La presente invención proporciona un péptido mimético de ApoA-I tal como se define en las reivindicaciones adjuntas.
A. Péptidos de Fórmula I
[0047] En una realización, se describen péptidos de 15 a 29 residuos que tienen la siguiente fórmula I
R1-Y1-X1-X2-X3-X4-X5-X6-X7-X8-X9-X10-X11-X12-X13-X14-X15-X16-X17-X18-X19-X20-X21-X22-X23-Y2-R2 Fórmula I
y sales farmacéuticamente aceptable de los mismos, en los que: X1 está ausente o es un residuo de aminoácido básico aquiral, D o L; X2 es un residuo de aminoácido básico aquiral, D o L; X3 es un residuo de aminoácido alifático aquiral, D o L; X4 es un residuo de aminoácido básico aquiral, D o L; X5 es Gln, Asn, D-Gln, D-Asn, o un residuo de aminoácido básico aquiral, D o L; X6 es Gln, Asn, D-Gln, D-Asn, o un residuo de aminoácido básico aquiral, D o L; X7 es un residuo de aminoácido hidrófobo aquiral, D o L; X8 es un residuo de aminoácido hidrófobo aquiral, D o L; X9 es un residuo de aminoácido hidrófilo aquiral, D o L; X10 es Leu, Trp, Gly, NaI, D-Leu, D-Trp, o D-NaI; X11 es Gly o un residuo de aminoácido alifático aquiral, D o L; X12 es un residuo de aminoácido hidrófilo aquiral, D o L; X13 es un residuo de aminoácido hidrófilo aquiral, D o L; X14 es Leu, Trp, Gly, D-Leu, o D-Trp; X15 es Leu, Gly, o D-Leu; X16 es un residuo de aminoácido ácido aquiral, D o L o un residuo de aminoácido básico aquiral, D o L; X17 es un residuo de aminoácido hidrófilo aquiral, D o L; X18 es Leu, Phe, D-Leu, o D-Phe; X19 es Leu, Phe, D-Leu, o D-Phe; X20 es un residuo de aminoácido ácido aquiral, D o L; X21 es Leu, Phe, D-Leu, o D-Phe; X22 es un residuo de aminoácido alifático aquiral, D o L; y X23 es Inp, Nip, azPro, Pip, azPip, D-Nip, o D-Pip; Y1 está ausente o es una secuencia de aminoácidos que tiene de 1 a 7 residuos; Y2 está ausente o es una secuencia de aminoácidos que tiene de 1 a 7 residuos; R1 es H o un grupo protector de amino; R2 es OH o un grupo protector de carboxilo; en los que de cero a ocho residuos X2 a X22 están ausentes; y en los que: a) cada residuo de aminoácido quiral es un residuo de L-aminoácido; b) cada residuo de aminoácido quiral es un residuo de D-aminoácido; c) cada residuo de aminoácido quiral es un residuo de L-aminoácido, a excepción de que uno o más de cada residuo de aminoácido terminal quiral y cada residuo de aminoácido quiral inmediatamente adyacente al mismo es un residuo de D-aminoácido; o d) cada residuo de aminoácido quiral es un residuo de D-aminoácido, a excepción de que uno o más de cada residuo de aminoácido terminal quiral y cada residuo de aminoácido quiral inmediatamente adyacente al mismo es un residuo de L-aminoácido.
[0048] En otra realización, se describen péptidos de 22 a 29 residuos que tienen la siguiente fórmula I:
R1-Y1-X1-X2-X3-X4-X5-X6-X7-X8-X9-X10-X11-X12-X13-X14-X15-X16-X17-X18-X19-X20-X21-X22-X23-Y2-R2 Fórmula I
y sales farmacéuticamente aceptable de los mismos, en la que: X1 está ausente o es un residuo de aminoácido básico aquiral, D o L; X2 es un residuo de aminoácido básico aquiral, D o L; X3 es un residuo de aminoácido alifático aquiral, D o L; X4 es un residuo de aminoácido básico aquiral, D o L; X5 es Gln, Asn, D-Gln, D-Asn, o un residuo de aminoácido básico aquiral, D o L; X6 es un residuo de aminoácido básico aquiral, D o L; X7 es un residuo de aminoácido hidrófobo aquiral, D o L; X8 es un residuo de aminoácido hidrófobo aquiral, D o L; X9 es un residuo de aminoácido hidrófilo aquiral, D o L; X10 es Leu, Trp, Gly, NaI, D-Leu, D-Trp, o D-NaI; X11 es Gly o un residuo de aminoácido alifático aquiral, D o L;
15
19 25
35
45
55
65
- o una sal farmacéuticamente aceptable del mismo.
[0065] En otra realización, X1 está ausente; X15 es Gly; y cada uno de X7, X8, X10, X11, y X14 es distinto de Gly. En una realización, el péptido de fórmula I es: Péptido 10 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Leu-Gly-Glu-Arg-Phe-Leu-Asp-Leu-Val-Inp (SEQ. ID. NO 10); o Péptido 102 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Leu-Gly-Glu-Arg-Phe-Leu-Asp-Leu-Val-Nip (SEQ. ID. NO. 102) Péptido 222 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Leu-Gly-Glu-Arg-Phe-Leu-Asp-Leu-Val-azPro (SEQ. ID. NO. 222) Péptido 314 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Leu-Gly-Glu-Arg-Phe-Leu-Asp-Leu-Val-Pip (SEQ. ID. NO. 314) Péptido 406 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Leu-Gly-Glu-Arg-Phe-Leu-Asp-Leu-Val-azPip (SEQ. ID. NO. 406)
- o una sal farmacéuticamente aceptable del mismo.
[0066] En otra realización, X1 está ausente; X14 es Gly; y cada uno de X7, X8, X10, X11, y X15 es distinto de Gly. En una realización, el péptido de fórmula I es: Péptido 11 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Gly-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Inp (SEQ. ID. NO 11); o Péptido 103 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Gly-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Nip (SEQ. ID. NO. 103) Péptido 223 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Gly-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-azPro (SEQ. ID. NO. 223) Péptido 315 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Gly-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Pip (SEQ. ID. NO. 315) Péptido 407 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Leu-Leu-Glu-Asn-Gly-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-azPip (SEQ. ID. NO 407)
- o una sal farmacéuticamente aceptable del mismo.
[0067] En otra realización, X1 está ausente; X10 es Gly; y cada uno de X7, X8, X11, X14, y X15 es distinto de Gly. En una realización, el péptido de fórmula I es: Péptido 12 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Gly-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Inp (SEQ. ID. NO 12); o Péptido 104 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Gly-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Nip (SEQ. ID. NO. 104) Péptido 224 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Gly-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-azPro (SEQ. ID. NO. 224) Péptido 316 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Gly-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Pip (SEQ. ID. NO. 316) Péptido 408 Lys-Leu-Lys-Gln-Lys-Leu-Ala-Glu-Gly-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-azPip (SEQ. ID. NO 408)
- o una sal farmacéuticamente aceptable del mismo.
[0068] En otra realización, X1 está ausente; X8 es Gly; y cada uno de X7, X10, X11, X14, y X15 es distinto de Gly. En una realización, el péptido de fórmula I es: Péptido 13 Lys-Leu-Lys-Gln-Lys-Leu-Gly-Glu-Leu-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Inp (SEQ. ID. NO 13); o Péptido 105 Lys-Leu-Lys-Gln-Lys-Leu-Gly-Glu-Leu-Leu-Glu-Asn-Leu-Leu-Glu-Arg-Phe-Leu-Asp-Leu-Val-Nip (SEQ. ID. NO. 105)
20
Claims (1)
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imagen1
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| HUE042314T2 (hu) | 2011-02-07 | 2019-06-28 | Cerenis Therapeutics Holding Sa | Lipoprotein komplexek és azok gyártása és alkalmazásai |
| US9644038B2 (en) | 2011-12-21 | 2017-05-09 | The Regents Of The University Of California | Apolipoprotein nanodiscs with telodendrimer |
| WO2013188879A1 (en) | 2012-06-16 | 2013-12-19 | Atherotech, Inc. | Measurement of serum lipoproteins |
| US9239280B2 (en) | 2012-06-16 | 2016-01-19 | Atherotech, Inc. | Measurement of serum lipoproteins |
| CA2947127A1 (en) | 2014-05-02 | 2015-11-19 | Cerenis Therapeutics Holding Sa | Hdl therapy markers |
| WO2016049061A1 (en) | 2014-09-22 | 2016-03-31 | Lawrence Livermore National Security, Llc | Electrochemical flow-cell for hydrogen production and nicotinamide co-factor dependent target reduction, and related methods and systems |
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| WO2017035326A1 (en) | 2015-08-25 | 2017-03-02 | Lawrence Livermore National Security, Llc | Stable nanolipoprotein particles and related compositions methods and systems |
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| US12083223B2 (en) | 2017-05-02 | 2024-09-10 | Lawrence Livermore National Security, Llc | Nanolipoprotein particles and related compositions methods and systems for loading RNA |
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