# US 11,029,303 B2 · PAH antibodies and uses thereof

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- Number: US 11,029,303 B2
- Document ID: US11029303B2
- Status: Granted
- Kind: B2
- Application number: 15/827,241
- Filed: 2017-11-30
- Published: 2018-08-16
- Granted: 2021-06-08
- Earliest claimed: 2015-06-01
- Assignees: The Administrators of the Tulane Educational Fund
- Applicants: The Administrators of the Tulane Educational Fund
- Inventors: Diane Blake; Yue Sun
- Web page: https://patentgrep.com/patent/US11029303B2

## CPC

- G01N 33/2835: {Specific substances contained in the oils or fuels}
- C07K 16/005: {constructed by phage libraries}
- C07K 16/44: against material not provided for elsewhere {, e.g. haptens, metals, DNA, RNA, amino acids}
- G01N 33/5308: {for analytes not provided for elsewhere, e.g. nucleic acids, uric acid, worms, mites}
- C07K 2317/33: Crossreactivity, e.g. for species or epitope, or lack of said crossreactivity
- C07K 2317/622: Single chain antibody (scFv)
- C07K 2317/92: Affinity (KD), association rate (Ka), dissociation rate (Kd) or EC50 value
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

The invention is directed to antibody compositions that specifically bind to polycyclic aromatic hydrocarbons (PAHs) and kits encompassing the same.

## Claims

### Claim 1

A recombinant antibody or fragment thereof that specifically binds to a polycyclic aromatic hydrocarbon (PAH), wherein the PAH is selected from the group consisting of naphthalene, acenapthene, acenapthylene, phenanthrene, fluorene, anthracene, benz[a]anthracene, chrysene, pyrene, fluoranthene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, indeno[1,2,3-cd]pyrene, benzol[ghi]perylene, and dibenz[a,h]anthracene,
wherein the recombinant antibody or fragment thereof comprises
a) a heavy chain with three CDRs comprising the amino acid sequences GYTFTSYWMH (SEQ ID NO: 60), EINPRNGRSNYNEKFKN (SEQ ID NO: 61), and DGGDY (SEQ ID NO: 62), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQDVGTAVA (SEQ ID NO: 63), WASTRHT (SEQ ID NO: 64), and QQYSSYPLT (SEQ ID NO: 65), respectively;
b) a heavy chain with three CDRs comprising the amino acid sequences GNTFTSYTMH (SEQ ID NO: 69), YINPSSGYTEYNQKFKD (SEQ ID NO: 70), and GPRY (SEQ ID NO: 71), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQNVGTNVA (SEQ ID NO: 72), SASYRYS (SEQ ID NO: 73), and QQYNSYPYT (SEQ ID NO: 74), respectively;
c) a heavy chain with three CDRs comprising the amino acid sequences GYTFTSYWMH (SEQ ID NO: 145), EINPSNGRTNYNEKFKS (SEQ ID NO: 77), and DGGDY (SEQ ID NO: 78), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQDVGTAVA (SEQ ID NO: 79), WASTRHT (SEQ ID NO: 80), and QQYSSYPLT (SEQ ID NO: 81), respectively;
d) a heavy chain with three CDRs comprising the amino acid sequences GYTFTSYWIVH (SEQ ID NO: 85), EINPRNGRSNYNEKFKN (SEQ ID NO: 86), and DGGDY (SEQ ID NO: 87), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQNVGTNVA (SEQ ID NO: 88), SASYRYS (SEQ ID NO: 89), and QQYNSYPLT (SEQ ID NO: 90), respectively;
e) a heavy chain with three CDRs comprising the amino acid sequences GYTFTSYWIVH (SEQ ID NO: 94), EINPRNGRSNYNEKFKN (SEQ ID NO: 95), and DGGDY (SEQ ID NO: 96), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQDVGTAVA (SEQ ID NO: 97), WASTRHT (SEQ ID NO: 98), and XQYXXYPLT (SEQ ID NO: 99), respectively;
f) a heavy chain with three CDRs comprising the amino acid sequences GYAFTKYLIE (SEQ ID NO: 103), VINPGSGSTSYNEKFRY (SEQ ID NO: 104), and IPASYRSDSLDC (SEQ ID NO: 105), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQDVGTAVA (SEQ ID NO: 106), WASTRHT (SEQ ID NO: 107), and QQYSSYPWT (SEQ ID NO: 108), respectively;
g) a heavy chain with three CDRs comprising the amino acid sequences GYTFTKYLIE (SEQ ID NO: 112), VINPGSGSTSYNEKFRYK (SEQ ID NO: 113), and IPASYRSDSLDC (SEQ ID NO: 114), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQDVGTAVA (SEQ ID NO: 115), WASTRHT (SEQ ID NO: 116), and QQYSSYPWT (SEQ ID NO: 117), respectively;
h) a heavy chain with three CDRs comprising the amino acid sequences GYAFTKYLIE (SEQ ID NO: 121), VINPGSGSTSYNEKFRY (SEQ ID NO: 122), and IPASYRSDSLDC (SEQ ID NO: 123), respectively, and a light chain with three CDRs comprising the amino acid sequences KASQDVGTAVA (SEQ ID NO: 124), WASTRHT (SEQ ID NO: 125), and QQYKSYPLT (SEQ ID NO: 126), respectively;
i) a heavy chain with three CDRs comprising the amino acid sequences GYVFTNFLIE (SEQ ID NO: 130), VINPGNGGAAYNEKFKG (SEQ ID NO: 131), and LPPSYDYDGDIDY (SEQ ID NO: 132), respectively, and a light chain with three CDRs comprising the amino acid sequences RASKSVTTSGYSLMH (SEQ ID NO: 133), PASNLES (SEQ ID NO: 134), and QHSRELPWT (SEQ ID NO: 135), respectively; or
j) a heavy chain with three CDRs comprising the amino acid sequences GYAFTNFLIE (SEQ ID NO: 139), VINPGSGGTGYNEKFKG (SEQ ID NO: 140), and LPPSYDYDGDIDY (SEQ ID NO: 141), respectively, and a light chain with three CDRs comprising the amino acid sequences RASKSVSSSGYSLIH (SEQ ID NO: 142), LASNLXS (SEQ ID NO: 143), and XHSXXLPWX (SEQ ID NO: 144), respectively.

### Claim 2 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein the PAH is petrogenic.

### Claim 3 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein the antibody specifically binds to phenanthrene, and wherein the antibody does not show substantial cross-reactivity against a PAH selected from the group consisting of naphthalene, acenapthene, acenapthylene, fluorene, anthracene, benz[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, benzol[ghi]perylene, and dibenz[a,h]anthracene.

### Claim 4 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein phenanthrene is methylated.

### Claim 5 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein the antibody or fragment thereof comprises a variable domain having a variable light chain (VL) amino acid sequence comprising SEQ ID NO: 58, 67, 76, 83, 92, 101, 110, 119, 128, or 137, or having a variable heavy chain (VH) amino acid sequence comprising SEQ ID NO:
57, 66, 75, 82, 91, 100, 109, 118, 127, or 136.

### Claim 6 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein the antibody or fragment thereof has an IC50 less than or equal to 8.3 μM.

### Claim 7 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein phenanthrene is 1-methylphenanthrene (1-MP), 2-methylphenanthrene (2-MP), 3-methylphenanthrene (3-MP), 4-methylphenanthrene (4-MP), 9-methylphenanthrene (9-MP), or 3,6-dimethylphenanthrene (3,6-DMP).

### Claim 8 (depends on 1)

The recombinant antibody or fragment thereof of claim 1, wherein the antibody or fragment thereof comprises the amino acid sequence of any one of SEQ ID NOS: 37-46.

### Claim 9 (depends on 1)

The recombinant antibody or fragment thereof of claim 1 encoded by a nucleic acid comprising any one of SEQ ID NOS: 47-56.

### Claim 10 (depends on 1)

A method of detecting the presence of a methylated PAH, the method comprising:
a) obtaining a sample;
b) contacting the sample with the recombinant antibody or fragment thereof of claim 1 for at least a period of time sufficient for the antibody or fragment thereof to bind its target; and
c) determining whether a methylated PAH is present in the sample.

### Claim 11 (depends on 10)

The method of claim 10, wherein the PAH is selected from the group consisting of naphthalene, acenapthene, acenapthylene, phenanthrene, fluorene, anthracene, benz[a]anthracene, chrysene, pyrene, fluoranthene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, indeno[1,2,3-cd]pyrene, benzol[ghi]perylene, and dibenz[a,h]anthracene.

### Claim 12 (depends on 11)

The method of claim 11, wherein phenanthrene is 1-methylphenanthrene (1-MP), 2-methylphenanthrene (2-MP), 3-methylphenanthrene (3-MP), 4-methylphenanthrene (4-MP), 9-methylphenanthrene (9-MP), or 3,6-dimethylphenanthrene (3,6-DMP).