Hydrazonyl sultones and uses thereof

A compound with aryl or heteroaryl groups and PET radionuclides is developed to address the lack of specificity and sensitivity in disease diagnosis, enabling enhanced PET imaging for targeted molecular detection.

HK40135165APending Publication Date: 2026-07-17THE RES FOUNDATION FOR THE STATE UNIV OF NEW YORK
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Patent Information

Authority / Receiving Office
HK · HK
Patent Type
Applications
Current Assignee / Owner
THE RES FOUNDATION FOR THE STATE UNIV OF NEW YORK
Filing Date
2026-05-19
Publication Date
2026-07-17

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Abstract

A compound comprising Formula I: (I) or Formula II: (II) where A is an aryl group or heteroaryl group, B is an aryl group, heteroaryl group, or alkyl group, and R is independently at each occurrence a H group, alkyl group, or halogenated alkyl group, or the two R groups are linked to form a ring. A probe comprising P-FRG or P-HS, where P is a probe group, HS is a hydrazonyl sultone group, FRG is a first reactive group. A method of diagnosing a disease in an individual, comprising administering one or more probe(s); administering i) if the probe(s) comprise(s) a hydrazonyl sultone group, one or more compound(s) comprising an alkenyl group or alkynyl group and one or more PET radionuclide group(s), or ii) if the probe(s) comprise(s) a first reactive group, one or more compound(s) comprising a hydrazonyl sultone group and one or more PET radionuclide group(s), and PET imaging the individual.
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Description

Abstract A compound comprising formula I: (I) or formula II: (II); wherein A is aryl or heteroaryl, B is aryl, heteroaryl, or alkyl, and R at each position is independently hydrogen-based, alkyl, or haloalkyl, or two R groups are linked to form a ring. A probe comprising P-FRG or P-HS, wherein P is a probe group, HS is a hydrazone sulfonyl group, and FRG is a first reactive group. A method for diagnosing an individual disease, the method comprising: administering one or more probes; (i) if the one or more probes comprise a hydrazone sulfonyl group, administering one or more compounds comprising an alkenyl or alkynyl group and one or more PET radionuclide groups; or (ii) if the one or more probes comprise a first reactive group, administering one or more compounds comprising a hydrazone sulfonyl group and one or more PET radionuclide groups, and performing PET imaging on the individual.

Claims

CLAIMS:

1. A compound comprising the following structure: a structural analog thereof, or a pharmaceutically a polymorph, or a stereoisomer, or a mixture ofan a wherein A is chosen from aryl groups, and heteroaryl groups, B is chosen from aryl groups, heteroaryl groups, and alkyl groups, and R is independently at each occurrence chosen from H group, alkyl groups, and halogenated alkyl groups, or the two R groups are linked to form a ring.

2. The compound of claim 1, wherein the compound comprises the following structure: O ROO O ,R1is independently at each occurrence chosen from H group, alkyl groups, halogenated alkyl groups, radionuclide groups, one or more imaging modalit(ies), and any combination thereof, and R2is independently at each occurrence chosen from H group, alkyl groups, halogenated alkyl groups, one or more imaging modalit(ies), and any combination thereof.

3. The compound of claim 2, wherein the one or more imaging modalit(ies) is / are independently at each occurrence chosen from fluorophore group(s) and PET radionuclide(s).

4. The compound of claim 3, wherein the PET radionuclide(s) is / are independently at each occurrence chosen from11C,13N,15O,18F,44Sc,64Cu,68Ga,82Rb,99mTc,123I,201Tl, and any combination thereof.

5. A compound of claim 2, wherein one or more R1and / or R2group(s) is / are independently at each occurrence chosen from carboxylic acid groups and carboxylate groups.

6. A compound of claim 1, wherein the compound comprises the following structure: , ,, 57. A composition comprising one or more compound(s) of claim 1.

8. A composition of claim 7, further comprising one or more pharmaceutical excipient(s).

9. A probe comprising: P-FRG or P-HS, wherein P is a probe group, HS is a hydrazonyl sultone group, FRG is a first reactive group, and wherein the hydrazonyl sultone group can react with a second reactive group to form a first 1,3- dipolar cycloaddition product, or wherein the first reactive group can react with a second reactive group to form a first 1,3-dipolar cycloaddition product.

10. The probe of claim 9, wherein the probe group is chosen from proteins, peptides, antibodies, structural analogs thereof, any fragments thereof, and any combinations thereof.

11. The probe of claim 9, wherein the first reactive group comprises an alkenyl group or an alkynyl group.

12. The probe of claim 11, wherein the first reactive group comprises a strained ring.

13. The probe of claim 12, wherein the strained ring is a BCN group chosen from [(1R,8S)-9- bicyclo[6.1.0]non-4-ynyl]methanol, bicyclo[6.1.0]non-4-yn-9-ylmethanol, bicyclo[6.1.0]non-4- yne, norbornenes, trans-cyclooctenes, cyclopropenes, spiroalkenes, cyclooctynes, and structural analogs thereof.

14. The probe of claim 9, wherein a compound comprising the second reactive group comprises one or more PET radionuclide group(s).

15. A composition comprising one or more probe(s) of claim 9.

16. A composition of claim 15, further comprising the composition further comprising one or more pharmaceutical excipient(s).

17. A method of diagnosing a current or potential disease, disease state, condition, disorder, side effect, or any combination thereof, in an individual, comprising: administering one or more probe(s) of claim 9; administering i) if the probe(s) comprise(s) a hydrazonyl sultone group, one or more compound(s) comprising an alkenyl group or alkynyl group and one or more PET radionuclide group(s), or ii) if the probe(s) comprise(s) a first reactive group, one or more compound(s) comprising a hydrazonyl sultone group and one or more PET radionuclide group(s), and PET imaging the individual, wherein the PET imaging is used to diagnose a current or potential disease, disease state, condition, disorder, side effect, or any combination thereof, in the individual.

18. A method of claim 17, wherein each first reactive group of the one or more probe(s) independently comprises an alkenyl or an alkynyl group.

19. A method of claim 17, wherein one or both of the administrations is / are intravenous.

20. A method of claim 17, wherein the current or potential disease, disease state, condition, disorder, side effect, or any combination thereof, is chosen from infections, cancers, neurological conditions / diseases, neurodegenerative diseases, psychological conditions / diseases, inflammatory conditions / diseases, cardio-vascular diseases, and any combination thereof.

21. A method of claim 17, wherein the cancer is chosen from brain cancers, melanomas, prostate cancer, breast cancer, lung cancer, and any combination thereof.

22. A method of claim 17, further comprising waiting for a duration of time between the two administering steps.

23. A method of claim 22, wherein the duration of time is 1 h to 3 weeks.

24. A method of claim 23, wherein the duration of time is 1 h to 1 week.

25. A method of claim 24, wherein the duration of time is 1 h to 4 h.

26. A method of claim 17, wherein the individual is human or a non-human animal.