Colchicine-Binding Site Inhibitors from Chemistry to Clinic: A Review
Abstract
:1. Microtubules as a Target for Treating Cancer
2. Colchicine: Historical Uses, Structure and Mechanism of Action
3. Targeting the Colchicine-Binding Site for Anti-Cancer Therapy
4. Colchicine-Binding Site Inhibitors Known before 2017
4.1. Combretastatin A-4 and Analogues
4.2. Successful Modifications of Combretastatin A-4
- (1)
- 3,4,5-trimethoxyphenyl-subsituted ring A.
- (2)
- 3-hydroxy-4-methoxyphenyl-substituted ring B.
- (3)
- cis double bond separating the two phenyl rings.
- (1)
- Three-membered ring bridges,
- (2)
- Six-membered ring bridges, and
- (3)
- Immobilized trimethoxyphenyl moieties.
4.2.1. Potent Chalcone Derivatives of CA-4
4.2.2. Phenstatin and Derivatives
4.2.3. IsoCA-4 and Selenium CA-4 Derivatives
4.3. New Combretastatin A-4 Analogues Reported between 2017 and 2019
4.3.1. New Combretastatin A-4 Analogues of 2017
β-Lactam Cis Restricted Analogues
β-Lactam CA-4 Analogues with an Azide Substituted B Ring
4.3.2. New Combretastatin A-4 Analogues of 2018
Dihydronapthalene Derivatives
Quinazolinone Derivatives
Photo-Responsive Azo CA-4 Analogues
Replacement of the Trimethoxyphenyl Moiety
4.3.3. New Combretastatin A-4 Analogues of 2019
ABI-231 Analogues
3-Vinyl Substituted β-Lactams
Pyrazole Analogues
Piperazine Conjugates
Oxazole-Bridged Analogues
Quinoline and Indole Derivatives of isoCA-4
Heterocyclic isoCA-4 Derivatives
Novel Benzosuberene Analogues
1,2,4-Triazole-3-Carboxamide Derivatives
5. CBSIs Derived from Sources Other Than Combretastatins
5.1. Podophyllotoxin and Analogues
5.2. Chalcones
5.2.1. Millepachine and Derivatives
5.2.2. New Quinolone Chalcones: CBSIs and Inhibitors of MRP1 Function
5.2.3. Quinoline-Chalcone Derivatives of 2019
5.3. Curacin A
5.4. Imidazo[4,5]pyridine DJ95 (DJ101)
5.5. 2-Methoxyestradiol and ENMD1198
5.6. Avanbulin (BAL27862) (75)
5.7. Nitrobenzoate IMB5046
5.8. Imidazole BZML
5.9. Crolibulin (MX-58151)
5.10. Novel Nicotinonitrile Analogues of Crolibulin and CA-4
5.11. Indenes CP248 and CP461
6. CBSIs in Clinical Trials and Clinical Use
6.1. Combretastatin A-4 Analogues in the Clinic
6.1.1. Fosbretabulin—A CA-4 Analogue Prodrug
6.1.2. Oxi4503—A CA-1 Prodrug
6.1.3. Ombrabulin/AVE8062—An CA-4 Amino Analogue Prodrug
6.2. Non-Combretastatin A-4 Analogues in Clinical Trials
6.2.1. Tivantinib
6.2.2. Plinabulin (BPI-2358, formerly NPI-2358)
6.2.3. Lisavanbulin (BAL101553)
6.2.4. Crolibulin
7. Conclusions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
AML | Acute myeloid leukaemia |
CA-1 | Combretastatin A-1 |
CA-4 | Combretastatin A-4 |
CA-4P | Combretastatin A-4 phosphate |
CBS | Colchicine-binding site |
CBSI | Colchicine-binding site inhibitor |
DAMA-colchicine | N-deacetyl-N-(2-mercaptoacetyl) colchicine |
DAPI | 4′,6-diamidino-2-phenylindole |
EGFR | Epidermal growth factor receptor |
FITC | Fluorescein isothiocyanate |
GDP | Guanosine diphosphate |
GEP-NETs | Gastro-entero-pancreatic neuroendocrine tumours |
GTP | Guanosine triphosphate |
HCC | Hepatocellular carcinoma |
HDAC | Histone deacetylase enzyme |
KRAS | Kirsten rat sarcoma viral analogue homologue |
MDR | Multi-drug resistance |
MDS | Myelodysplastic syndrome |
MTA | Microtubule-targeting agent |
NLRP3 | nucleotide-binding domain (NOD)-like receptor protein |
NSCLC | Non-small-cell lung carcinoma |
P-gp | P-glycoprotein |
PPTP | Paediatric preclinical testing program |
SAR | Structure–activity relationship |
UGT | UDP-glucuronyl transferase |
VDA | Vascular-disrupting agent |
VEGFR | Vascular endothelial growth factor receptor |
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Drug Name | Section | Structural Features | Stage in Clinical Trials and Disease Treated | Company Developing Drug |
---|---|---|---|---|
ENMD1198 (74) | Section 5.5 | 2-Methoxyestradiol derivative | Phase I refractory solid tumours | Casi pharmaceuticals (no data published in recent years) |
CP461/OSI-461 (82) | Section 5.11 | Derivative of exisulind | Phase II
| Astellas |
Tivantinib (86) | Section 6.2.1 | Heterocyclic fused ring system | Phase II
| Kyowa Hakko Kirin Co. Ltd. (development discontinued in 2018 following multiple poor clinical trial outcomes) |
Plinabulin (75b) | Section 6.2.2 | Piperazinedione structure | Phase III stage IIIb/IV NSCLC (in combination with docetaxel) | Beyond Spring Inc. |
Lisavanbulin (BAL101553) (87) | Section 6.2.3 | Lysine prodrug of Avanbulin | Phase I/IIa advanced solid tumours, refractory to standard therapy | Basilea Pharmaceutica |
Crolibulin (78) | Section 6.2.4 | Chromene derivative | Phase I/II Clinical trials Anaplastic Thyroid Cancer | Immune Pharmaceuticals Inc; National Cancer Institute (USA) (clinical trial progression limited due to recruitment issues) |
Drug Name | Section | Structural Features | Stage in Clinical Trials and Disease Treated | Company Developing Drug |
---|---|---|---|---|
Fosbretabulin (83) | Section 6.1.1 | Phosphate prodrug of CA-4 | Phase I/II/III
| Diamond Biopharm Limited |
Oxi4503 (84) | Section 6.1.2 | DiPhosphate prodrug of CA-1 | Phase Ib/II
| Mateon Therapeutics (previously Oxigene) |
Ombrabulin/AVE8062 (85) | Section 6.1.3 | Serine prodrug of CA-4 | Phase II
| Sanofi Aventis |
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McLoughlin, E.C.; O’Boyle, N.M. Colchicine-Binding Site Inhibitors from Chemistry to Clinic: A Review. Pharmaceuticals 2020, 13, 8. https://doi.org/10.3390/ph13010008
McLoughlin EC, O’Boyle NM. Colchicine-Binding Site Inhibitors from Chemistry to Clinic: A Review. Pharmaceuticals. 2020; 13(1):8. https://doi.org/10.3390/ph13010008
Chicago/Turabian StyleMcLoughlin, Eavan C., and Niamh M. O’Boyle. 2020. "Colchicine-Binding Site Inhibitors from Chemistry to Clinic: A Review" Pharmaceuticals 13, no. 1: 8. https://doi.org/10.3390/ph13010008