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US 2025/0085251 A1Published application
Polycyclic aromatic bridges for molecular electronic sensors
AssigneeRoswell Biotechnologies, Inc.
InventorsBarry Merriman, Tim Geiser, Paul W. Mola, Darryl Rideout
Life of this patent
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Abstract
In various embodiments, synthetic bridge molecules are disclosed, usable in molecular electronics sensors. In various aspects, bridge molecules comprise fused ring polycyclic aromatic hydrocarbon structures in the shape of a long and narrow ribbon, with end groups on opposite short ends for selective binding to metal electrodes, one or more substituents near the midpoint of a long edge for binding to a probe molecule, and one or more additional substituent groups for solubility or other effects. In various embodiments, the bridge molecules herein are conducting, and provide a closed circuit in a sensor when forming a bridge between gapped electrodes.
Claims13
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising:
- an electrically conductive sp2-hybridized polycyclic aromatic hydrocarbon nanoribbon of fused benzene rings each in a single fixed orientation, the nanoribbon having a generally rectangular sheet-like configuration and a periphery defined by two substantially parallel longer top and bottom edges and two substantially parallel shorter left and right edges, wherein the single fixed orientation of each fused ring results in a zig-zag periodicity along either the longer edges or the shorter edges of the nanoribbon, and wherein the nanoribbon measures from about 3 nm to about 100 nm in length and from about 0.23 nm to about 23 nm in width;
- a substituent L covalently bonded to the left shorter edge of the nanoribbon;
- a substituent R covalently bonded to the right shorter edge of the nanoribbon, wherein L and R each comprise at least one sulfur atom or a carbene precursor moiety capable of bonding to a metal electrode or a metal contact disposed on an electrode;
- at least one attachment group P covalently bonded to any edge of the nanoribbon and capable of bonding to a probe molecule;
- and
- at least one substituent S covalently bonded to any edge of the nanoribbon, the substituent capable of affecting at least one of solubility or conformation of the synthetic bridge molecule or capable of promoting self-assembly of the synthetic bridge molecule to at least one of the metal electrode, the metal contact on an electrode, or the probe molecule, in fabrication of the molecular electronics sensor.
3 more elements
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising the structure:
- wherein:
- n and m are independently 0 to 30;
- W and Y are independently selected from —O—, —CH2—, CR8R9, CH2CR8R9, CR8CR9CH2, OCR8R9, and CR8R9O, wherein R8 and R9 are attached to the same carbon atom and independently selected from H, CH3, C2H5, CH2CH2CH3, or (CH2)x(OCH2CH2)yOR10, wherein x is 2 to 10, y is 10 to 40 and R10 is H, Me, or Et, and wherein R8 and R9 can optionally link to form a ring, wherein O is optionally linked directly to the aromatic ring, and wherein W and Y can optionally be exchanged with one another within a ring;
- W′ and Y′ are independently selected from —O—, —CH2—, CR8R9, CH2CR8R9, CR8CR9CH2, OCR8R9, and CR8R9O, wherein R8 and R9 are attached to the same carbon atom and independently selected from H, CH3, C2H5, CH2CH2CH3, or (CH2)x(OCH2CH2)yOR10, wherein x is 2 to 10, y is 10 to 40 and R10 is H, Me, or Et, and wherein R8 and R9 can optionally link to form a ring, wherein O is optionally linked directly to the aromatic ring, and wherein W′ and Y′ can optionally be exchanged with one another within a ring;
- R1 is a moiety selected from (i) ester linked PEG chains (CH2)xCO(OCH2CH2)yOR13 or (CH2)xOC—OCH2CH2CH2 (OCH2CH2)yOR13, wherein x is from 0 to 10, y is from 10 to 40, and R13 is Me or H:
- or (ii) a water-soluble, ester-linked dendron comprising 8 to 64 branches, each derivatized with water-solubilizing PEG chains of structure (CH2CH2O)zR14, wherein z is from 1 to 8 and R14 is H or Me, wherein the ester-linkage of R1 optionally comprises a 1) photocleavable, 2) redox-cleavable, 3) acid cleavable or 4) base-cleavable linker such that the dendron can be removed using 1) light, 2) an oxidizing or reducing agent, 3) an acid or 4) a base, respectively;
- R2 is a moiety selected from (i) ester linked PEG chains (CH2)xCO(OCH2CH2)yOR13 or (CH2)xOC—OCH2CH2CH2 (OCH2CH2)yOR13 wherein x is from 0 to 10, y is from 10 to 40, and R13 is Me or H:
- (ii) a water-soluble, ester-linked dendron linked from the nanoribbon with 4 to 16 branches, each derivatized with water-solubilizing PEG chains (CH2CH2O)zR14 wherein z is from 1 to 4 and R14 is H or Me, wherein the ester-linkage of R2 optionally comprises a 1) photocleavable, 2) redox-cleavable, 3) acid cleavable or 4) base-cleavable linker such that the dendron can be removed using 1) light, 2) an oxidizing or reducing agent, 3) an acid or 4) a base, respectively;
- W″ and Y″ are independently selected from —S—, —CH2—, CH2CH2, CR11R12, and SCR11R12, wherein R11 and R12 are bonded to the same carbon atom and independently selected from H, CH3, C2H5, CH2CH2CH3, CH2CH2SCH3, SCH3, or SCH2CH2SCH3, and wherein R8 and R9 can optionally link to form a ring, wherein S is optionally linked directly to the aromatic ring, and wherein W″ and Y″ can optionally be exchanged with one another within a ring;
- R5 is H, SMe, or CH2CH2SMe;
- R6 is H, SMe, SCH2CH2SMe, SCH2C(CH2SMe)3, SH, CS2H, CH2SMe, CH2SH, CH2CS2H, 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-yl or 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-thioyl;
- and
- R7 is H, SMe, SCH2CH2SMe, SH, CS2H, CH2SMe, CH2SH, CH2CS2H, 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-yl or 6-[1,3-diisopropyl-1H-benzo[d]imidazol-3-ium]-thioyl.
10 more elements
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising the structure,
- wherein:
- n=2;
- m=3 to 500;
- R1 is selected from:
- (1) an ester linked PEG chain having the structure (CH2)xCO(OCH2CH2)yOR13 or (CH2)xOC—OCH2CH2CH2(OCH2CH2)yOR13, wherein x is from 3 to 10, y is from 10 to 40, and R13 is Me or H;
- (2) an ether linked PEG chain having the structure (CH2)xO—CH2CH2CH2(OCH2CH2)yOR13, wherein x>2, y is from 10 to 40, and R13 is Me or H;
- or (3) a water-soluble ester-linked dendron, comprising 8 to 64 branches, each derivatized with water-solubilizing PEG chains (CH2CH2O)zR14, wherein z is from 1 to 8 and R14 is H or Me;
- and wherein the ester-linkage of R1 can optionally include a 1) photocleavable, 2) redox-cleavable, 3) acid cleavable or 4) base-cleavable linker so that the dendron can be removed using 1) light, 2) an oxidizing or reducing agent, 3) an acid or 4) a base, respectively, after the cap portion of the molecule is linked to gold electrodes;
- R2 is selected from:
- (1) an ester linked PEG chain having the structure (CH2)xCO(OCH2CH2)yOR13 or (CH2)xOC—OCH2CH2CH2(OCH2CH2)yOR13, wherein x is from 3 to 10, y is from 10 to 40, and R13 is Me or H;
- (2) an ether linked PEG chain having the structure (CH2)xO—CH2CH2CH2(OCH2CH2)yOR13, wherein x>2, y is from 10 to 40, and R13 is Me or H;
- or (3) —H;
- R3=—(CH2)nC(O)NH—CH[(CH2)/(CH2)R18][CH2CH2—O—CH2CH2O—(CH2)s—R19), wherein n, r and s are independently between 2 and 7;
- and wherein R18 and R19 are independently selected from —N3, —CC—H, —NHCO-biotin, —CHO, —COCH3 and —O—NH2, with the proviso that R18 and R19 cannot react with one another;
- R4 is H or SCH2CH2SCH3;
- and
- R5 is-SH or SCH2CH2SCH3.
14 more elements
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising the structure,
- wherein:
- n and m are independently 0 to 30;
- R1=R2=—(CH2)4C(O)O-PEG-48;
- R3=H or —NR9R10, wherein R9 is linked to a DNA polymerase cysteine residue and R10 is either H or R10 forms a ring with R9 that does not include the polymerase, or R10 is linked to a DNA polymerase cysteine residue that is distinct from the residue linked to R9.
- R4=R5=H
- R6=CH2SCH2CH2SCH3 or H;
- R7=CH2SCH2CH2SCH3 or H;
- and
- R8=CH2SCH2CH2SCH3 or —SH.
6 more elements
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising the structure:
- wherein n is an integer chosen such that the length of the synthetic bridge molecule is from about 5 nm to about 30 nm.
A synthetic bridge molecule for use in a molecular electronics sensor, the molecule comprising the structure:
Dependencies are inferred from the claim text.