US2006240562A1PendingUtilityA1
Cleavable surfactants and methods of use thereof
Est. expiryMay 29, 2021(expired)· nominal 20-yr term from priority
C07F 9/10C07C 327/22C07C 255/41C07F 7/081C07C 65/03C07C 69/732Y10T436/25375Y10T436/107497Y10T436/10C07D 213/20C07F 9/092
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Claims
Abstract
Cleavable compositions and methods of use especially in MALDI MS analysis of hydrophobic proteins.
Claims
exact text as granted — not AI-modified1 - 35 . (canceled)
36 . A compound, comprising: a cleavable surfactant including a MALDI matrix composition and a hydrophobic group joined together by a cleavable linker.
37 . The compound of 36 , wherein the cleavable linker is a disulfide linker, a thioester linker, or a ketal linker.
38 . The compound of claim 36 , comprising: a cleavable surfactant including a cinnamic group and a hydrophobic group joined together by a cleavable linker.
39 . The compound of claim 36 , comprising: a sinapinic group and a hydrophobic group joined together by a cleavable linker.
40 . A compound of the following Formula:
or a salt thereof, wherein:
Y is a group —H, —OH, or —(CH2) n OH independently on each of C4, C5, or C6 and
wherein n is an integer of from 1 to 5 and wherein Y is H or C3;
X is a group OH or NH2; and
R is a group (CH 2 )mCH 3 , wherein m is an integer of from 1 to 19.
41 . The compound of claim 40 , wherein X is OH.
42 . The compound of claim 40 , wherein R is a group —(CH 2 ) 3 CH 3 , —(CH 2 ) 4 CH 3 , —(CH 2 ) 5 CH 3 , —(CH 2 ) 6 CH 3 , or —(CH 2 ) 7 CH 3 .
43 . A compound of the following formula:
or a salt thereof, wherein:
Y is a group —N(CH 3 ) 2 (CH 2 ) 3 SO 3 − , —N + (CH 3 ) 3 , —SO 3 − , or —SO 4 − , independently on each of C4, C5, or C6 and wherein Y is —H on C3;
X is a group OH or NH2; and
R is a group (CH 2 )mCH 3 , wherein m is an integer of from 1 to 19.
44 . The compound of claim 43 , wherein X is OH.
45 . The compound of claim 43 , wherein R is a group —(CH 2 ) 3 CH 3 , —(CH 2 ) 4 CH 3 , —(CH 2 ) 5 CH 3 , —(CH 2 ) 6 CH 3 , or —(CH 2 ) 7 CH 3 .
46 . A compound of the following formula:
or a salt thereof, wherein:
Y is a group —H, —OH, —(CH2) n OH, —N(CH 3 ) 2 (CH 2 ) 3 SO 3 − , —N + (CH 3 ) 3 , —SO 3 − , or —SO 4 − , independently on each of C4, C5, or C6 and wherein n is an integer of from 1 to 5 and wherein Y is H on C3; and
X is a group —OH or —NH2.
47 . A compound of the formula:
or a salt thereof.
48 . A method for isolating a hydrophobic molecule, comprising:
providing a plasma comprising a hydrophobic molecule; applying a cleavable surfactant with a polar head group and a hydrophobic tail to the plasma so that the surfactant engages the hydrophobic molecule; cleaving the surfactant from the hydrophobic molecule, and analyzing said hydrophobic molecule.
49 . The method of claim 48 , further comprising the step of:
analyzing said hydrophobic molecule.
50 . The method of claim 49 , wherein said analyzing step comprises MALDI MS.
51 . The method of claim 48 , wherein said hydrophobic molecule is a polymer, peptide, polypeptide, proteins, components of a cell sample, component of a tissue sample, lipid, or extracellular component.
52 . The method of claim 48 , further comprising an enzymatic digestion step of the hydrophobic molecule, said enzymatic digestion step occurring either before or after said cleaving step.
53 . The method of claim 49 , wherein the polar head group is a MALDI MS matrix or precursor thereof.
54 . The method of claim 49 , wherein the polar head group comprises a cinnamic acid, derivatives of cinnamic acid, sinapinic acid, alpha-cyano-4-hydroxycinnamic acid (αCHCA), or 2,5-dihydroxybenzoic acid (2,5-DHB).
55 . The method of claim 48 , wherein the cleavable surfactant/detergent compound of the following formula:
56 . The method of claim 55 , wherein the hydrophobic tail comprises an alkyl, alkenyl, or alkynyl group containing 2-20 carbons.
57 . The method of claim 55 , wherein the cleavable linker is acid cleavable, fluoride cleavable, photocleavable, or a disulfide/thioester,
58 . The method of claim 57 , wherein the cleavable linker is selected from the following:
where R 1 is independently —H or —(CH 2 ) 0-19 CH 3 ;
where R 1 is independently —CH 3 ,
X is a group NH 2 or OH. R 1 is —H, —CH 3 , —F, —Cl, —Br, —I, or, —CN. Head groups are attached independently on each of C4, C5, and C6.
59 . The method of claim 55 , wherein the polar head is cationic, anionic, Zwitterionic, a non-ionic carbohydrate, or a MALDI matrix.
60 . The method of claim 59 , wherein the polar head group is selected from N + [(CH) 0-3 CH 3 ] 3 , P + [(CH) 0-3 CH 3 ] 3 ,
wherein n is 1-12; cystine; cystine containing peptides with 6 amino acids or less; furanose; pyranose; polysaccharides with 3 carbohydrates or less; polyethylene glycol; sinapinic acid MALDI matrices; α-cyano-4-hydroxycinnamic acid MALDI matrices; 2,5-dihydroxybenzoic acid; MALDI matrices; and 3,5-dihydroxybenzoic acid MALDI matrices.
61 . A cleavable surfactant/detergent compound of the following formula:
62 . The compound of claim 61 , wherein the MALDI matrix is a sinapinic acid MALDI matrix, α-cyano-4-hydroxycinnamic acid MALDI matrix, 2,5-dihydroxybenzoic acid; MALDI matrix, or a 3,5-dihydroxybenzoic acid MALDI matrices.
63 . A method of isolating a hydrophobic sample comprising contacting said sample with a compound of claim 62 .
64 . A method of performing electrophoresis on a sample, comprising
contacting said sample with a surfactant that is subsequently cleavable from sample, said surfactant being selected from wherein said cleavable linker is acid cleavable, fluoride cleavable, photocleavable, or a disulfide/thioester,
65 . A cleavable surfactant/detergent compound of the following formula:
66 . The compound of claim 65 , wherein the hydrophobic tail comprises an alkyl, alkenyl, or alkynyl group containing 2-20 carbons.
67 . The compound of claim 65 , wherein the cleavable linker is acid cleavable, fluoride cleavable, photocleavable, or a disulfide/thioester,
68 . The compound of claim 67 , wherein the cleavable linker is selected from the following:
where R 1 is independently —H or —(CH 2 ) 0-19 CH 3 ,
R 1 is independently —CH 3 ,
X is a group NH 2 or OH. R 1 is —H, —CH 3 , —F, —Cl, —Br, —I, or, —CN. Head groups are attached independently on each of C4, C5, and C6.
69 . The compound of claim 65 , wherein the polar head is cationic, anionic, Zwitterionic, a non-ionic carbohydrate, or a MALDI matrix.
70 . The compound of claim 69 , wherein the polar head group is selected from
N + [(CH) 0-3 CH 3 ] 3 , P + [(CH) 0-3 CH 3 ] 3 , wherein n is 1-12; cystine; cystine containing peptides with 6 amino acids or less; furanose; pyranose; polysaccharides with 3 carbohydrates or less; polyethylene glycol; sinapinic acid MALDI matrices; α-cyano-4-hydroxycinnamic acid MALDI matrices; 2,5-dihydroxybenzoic acid; MALDI matrices; and 3,5-dihydroxybenzoic acid MALDI matrices.
71 . A compound of claim 65 , of the following formula:
72 . A compound of claim 65 , of the following formula:Cited by (0)
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