Bi-functional compound positively charged at first ph and negatively charged at second ph, solid support comprising the bi-functional compound, and method of isolating nucleic acid using the same

A solid support on which a bi-functional compound is immobilized, comprising:

• a substrate, and
• a bi-functional compound immobilized on the substrate, the bi-functional compound being positively charged at a first pH and negatively charged at a second pH, and represented by Formula I below:
• Q-X-Q1 (Formula I)
• wherein Q or Q1 is a group represented by —X1—R1—Y1 where X1 is —O—, —S—, or —NR2— or a combination comprising at least one of the foregoing, where R2 is hydrogen, halogen, and a substituted or unsubstituted C1-C10 alkyl, R1 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, a substituted or unsubstituted C2-C10 alkynylene, r a combination comprising at least one of the foregoing, Y1 is a group represented by
• where R3 and R4 are each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, or R3 and R4 are bound to each other to form an alicyclic or aromatic group, or Y1 is a group that is represented by
• and has a 4- to 8-membered alicyclic ring or a 6- to 8-membered aromatic ring where R6 and R7 are each independently hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, with a proviso that R6 is not halogen, at least one of Q and Q1 has a primary or secondary amino group,
• X is a compound represented by
• wherein L is a bond, —O—, —CO—, —S—, —SO2—, —CH2—, —C(CH3)2—, —C(CF3)2—, or a combination comprising at least one of the foregoing,
• wherein the carbonyl group and the carboxyl group are substituted at any available carbon position except for a ring connection portion,
• or a combination comprising at least one of the foregoing, or
• a bi-functional compound that is positively charged at a first pH and negatively charged at a second pH, wherein the bi-functional compound is linked to at least one monomer comprising monomers represented by M0, M1, M2, M3, or a combination comprising at least one of the foregoing, below, and wherein the bi-functional compound comprises at least one of a monomer with A and at least one of a monomer with B,
• wherein A is a group represented by —OH or —X2—R11—Y2 where X2 is O—, —S—, —NR12—, or a combination comprising at least one of the foregoing, where R12 is hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, or a combination comprising at least one of the foregoing, R11 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, a substituted or unsubstituted C2-C10 alkynylene, or a combination comprising at least one of the foregoing, and Y2 is —COOH, —SO3H, —SO2H, —SOH, —H2PO4, —HPO4−, —PO42−, or a combination comprising at least one of the foregoing,
• B is a group represented by —X3—R13—Y3 where X3 is O—, —S—, —NR14—, or a combination comprising at least one of the foregoing, where R14 is hydrogen, halogen, and a substituted or unsubstituted C1-C10 alkyl, R13 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, and a substituted or unsubstituted C2-C10 alkynylene, or a combination comprising at least one of the foregoing, Y3 is a group represented by
• where R3 and R4 are each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, or R3 and R4 are bound to each other to form an alicyclic or aromatic ring, or Y3 is a group that is represented by
• and has a 4- to 8-membered alicyclic ring or a 6- to 8-membered aromatic ring where R6 and R7 are each independently hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, with a proviso that R6 is not halogen, R8 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, a substituted or unsubstituted C2-C10 alkynylene, or a combination comprising at least one of the foregoing, R9 and R10 are each independently hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, wherein the bi-functional compound comprising A and B has a polymerization degree of about 2 to about 30,000.

A method of isolating a nucleic acid, the method comprising:

• contacting a bi-functional compound with a sample comprising a nucleic acid at a first pH;
• and
• exposing the bi-functional compound with the nucleic acid bound thereto at a second pH that is higher than the first pH to release the nucleic acid from the bi-functional compound,
• the bi-functional compound being positively charged at a first pH and negatively charged at a second pH, and represented by Formula I below:
• Q-X-Q1 (Formula I)
• wherein Q or Q1 is a group represented by —X1—R1—Y1 where X1 is —O—, —S—, or —NR2— or a combination comprising at least one of the foregoing, where R2 is hydrogen, halogen, and a substituted or unsubstituted C1-C10 alkyl, R1 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, a substituted or unsubstituted C2-C10 alkynylene, r a combination comprising at least one of the foregoing, Y1 is a group represented by
• where R3 and R4 are each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, or R3 and R4 are bound to each other to form an alicyclic or aromatic group, or Y1 is a group that is represented by
• and has a 4- to 8-membered alicyclic ring or a 6- to 8-membered aromatic ring where R6 and R7 are each independently hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, with a proviso that R6 is not halogen, at least one of Q and Q1 has a primary or secondary amino group,
• X is a compound represented by
• wherein L is a bond, —O—, —CO—, —S—, —SO2—, —CH2—, —C(CH3)2—, —C(CF3)2—, or a combination comprising at least one of the foregoing,
• wherein the carbonyl group and the carboxyl group are substituted at any available carbon position except for a ring connection portion,
• or a combination comprising at least one of the foregoing, or
• a bi-functional compound that is positively charged at a first pH and negatively charged at a second pH, wherein the bi-functional compound is linked to at least one monomer comprising monomers represented by M0, M1, M2, M3, or a combination comprising at least one of the foregoing, below, and wherein the bi-functional compound comprises at least one of a monomer with A and at least one of a monomer with B,
• wherein A is a group represented by —OH or —X2—R11—Y2 where X2 is —O—, —S—, —NR12—, or a combination comprising at least one of the foregoing, where R12 is hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, or a combination comprising at least one of the foregoing, R11 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, a substituted or unsubstituted C2-C10 alkynylene, or a combination comprising at least one of the foregoing, and Y2 is —COOH, —SO3H, —SO2H, —SOH, —H2PO4, —HPO4−, —PO42−, or a combination comprising at least one of the foregoing,
• B is a group represented by —X3—R13—Y3 where X3 is O—, —S—, —NR14—, or a combination comprising at least one of the foregoing, where R14 is hydrogen, halogen, and a substituted or unsubstituted C1-C10 alkyl, R13 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, and a substituted or unsubstituted C2-C10 alkynylene, or a combination comprising at least one of the foregoing, Y3 is a group represented by
• where R3 and R4 are each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, or R3 and R4 are bound to each other to form an alicyclic or aromatic ring, or Y3 is a group that is represented by
• and has a 4- to 8-membered alicyclic ring or a 6- to 8-membered aromatic ring where R6 and R7 are each independently hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, with a proviso that R6 is not halogen, R8 is a substituted or unsubstituted C1-C10 alkylene, a substituted or unsubstituted C3-C10 cycloalkylene, a substituted or unsubstituted C2-C10 alkenylene, a substituted or unsubstituted C2-C10 alkynylene, or a combination comprising at least one of the foregoing, R9 and R10 are each independently hydrogen, halogen, a substituted or unsubstituted C1-C10 alkyl, a substituted or unsubstituted C3-C10 cycloalkyl, a substituted or unsubstituted C2-C10 alkenyl, a substituted or unsubstituted C2-C10 alkynyl, or a combination comprising at least one of the foregoing, wherein the bi-functional compound comprising A and B has a polymerization degree of about 2 to about 30,000.

A solid support on which a bi-functional compound is immobilized, comprising the sequential reaction product of:

• a substrate,
• a surface treatment agent,
• a dianhydride or polyanhydride, and
• a nitrogen-containing compound,
• wherein the bi-functional compound is positively charged at a first pH and negatively charged at a second pH.