ADPM06
ADPM06 is an emerging non-porphyrin PDT agent which has been specifically designed for therapeutic application. It was demonstrated that ADPM06-PDT was well tolerated in vivo and elicited impressive complete response rates in various models of cancer when a short drug-light interval was applied. Using a drug and light combination that reduced the clonogenicity of MDA-MB-231 cells by >90%. PDT-induced apoptosis was also found to be independent of p53 tumor suppressor status. A robust therapeutic response in vivo was demonstrated, with a substantial reduction in tumor proliferation observed, as well as a rapid induction of apoptosis and initiation of ER stress, mirroring numerous aspects of the mechanism of action of ADPM06 in vitro. Finally, using a combination of (18) F-labeled 3'-deoxy-3'-fluorothymidine ((18) F-FLT) nuclear and optical imaging, a considerable decrease in tumor proliferation over 24-hr in two models of human cancer was observed. Taken together, this data clearly establishes ADPM06 as an exciting novel PDT agent with significant potential for further translational development. (source
1: O'Connor AE, McGee MM, Likar Y, Ponomarev V, Callanan JJ, O'shea DF, Byrne AT, Gallagher WM. Mechanism of cell death mediated by a BF(2) -chelated tetraryl-azadipyrromethene photodynamic therapeutic: Dissection of the apoptotic pathway in vitro and in vivo. Int J Cancer. 2011 Mar 16. doi: 10.1002/ijc.26073. [Epub ahead of print] PubMed PMID: 21413012.
2: Flavin K, Lawrence K, Bartelmess J, Tasior M, Navio C, Bittencourt C, O'Shea DF, Guldi DM, Giordani S. Synthesis and characterization of boron azadipyrromethene single-wall carbon nanotube electron donor-acceptor conjugates. ACS Nano. 2011 Feb 22;5(2):1198-206. Epub 2011 Feb 3. PubMed PMID: 21291283.
3: Byrne AT, O'Connor AE, Hall M, Murtagh J, O'Neill K, Curran KM, Mongrain K, Rousseau JA, Lecomte R, McGee S, Callanan JJ, O'Shea DF, Gallagher WM. Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessment. Br J Cancer. 2009 Nov 3;101(9):1565-73. Epub 2009 Oct 13. PubMed PMID: 19826417; PubMed Central PMCID: PMC2778519.
4: Teets TS, Updegraff JB, Esswein AJ, Gray TG. Three-coordinate, phosphine-ligated azadipyrromethene complexes of univalent group 11 metals. Inorg Chem. 2009 Sep 7;48(17):8134-44. PubMed PMID: 19655715.
5: Loudet A, Bandichhor R, Wu L, Burgess K. Functionalized BF(2) Chelated Azadipyrromethene Dyes. Tetrahedron. 2008 Apr 21;64(17):3642-3654. PubMed PMID: 19458781; PubMed Central PMCID: PMC2390871.
6: Teets TS, Partyka DV, Updegraff JB 3rd, Gray TG. Homoleptic, four-coordinate azadipyrromethene complexes of d10 zinc and mercury. Inorg Chem. 2008 Apr 7;47(7):2338-46. Epub 2008 Feb 27. PubMed PMID: 18311885.
7: Teets TS, Partyka DV, Esswein AJ, Updegraff JB 3rd, Zeller M, Hunter AD, Gray TG. Luminescent, three-coordinate azadipyrromethene complexes of d(10) copper, silver, and gold. Inorg Chem. 2007 Aug 6;46(16):6218-20. Epub 2007 Jul 14. PubMed PMID: 17630731.
8: Killoran J, O'Shea DF. Impact of a conformationally restricted receptor on the BF2 chelated azadipyrromethene fluorosensing platform. Chem Commun (Camb). 2006 Apr 14;(14):1503-5. Epub 2006 Feb 27. PubMed PMID: 16575441.
9: Hall MJ, Allen LT, O'Shea DF. PET modulated fluorescent sensing from the BF2 chelated azadipyrromethene platform. Org Biomol Chem. 2006 Mar 7;4(5):776-80. Epub 2006 Jan 19. PubMed PMID: 16493459.
2: Flavin K, Lawrence K, Bartelmess J, Tasior M, Navio C, Bittencourt C, O'Shea DF, Guldi DM, Giordani S. Synthesis and characterization of boron azadipyrromethene single-wall carbon nanotube electron donor-acceptor conjugates. ACS Nano. 2011 Feb 22;5(2):1198-206. Epub 2011 Feb 3. PubMed PMID: 21291283.
3: Byrne AT, O'Connor AE, Hall M, Murtagh J, O'Neill K, Curran KM, Mongrain K, Rousseau JA, Lecomte R, McGee S, Callanan JJ, O'Shea DF, Gallagher WM. Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessment. Br J Cancer. 2009 Nov 3;101(9):1565-73. Epub 2009 Oct 13. PubMed PMID: 19826417; PubMed Central PMCID: PMC2778519.
4: Teets TS, Updegraff JB, Esswein AJ, Gray TG. Three-coordinate, phosphine-ligated azadipyrromethene complexes of univalent group 11 metals. Inorg Chem. 2009 Sep 7;48(17):8134-44. PubMed PMID: 19655715.
5: Loudet A, Bandichhor R, Wu L, Burgess K. Functionalized BF(2) Chelated Azadipyrromethene Dyes. Tetrahedron. 2008 Apr 21;64(17):3642-3654. PubMed PMID: 19458781; PubMed Central PMCID: PMC2390871.
6: Teets TS, Partyka DV, Updegraff JB 3rd, Gray TG. Homoleptic, four-coordinate azadipyrromethene complexes of d10 zinc and mercury. Inorg Chem. 2008 Apr 7;47(7):2338-46. Epub 2008 Feb 27. PubMed PMID: 18311885.
7: Teets TS, Partyka DV, Esswein AJ, Updegraff JB 3rd, Zeller M, Hunter AD, Gray TG. Luminescent, three-coordinate azadipyrromethene complexes of d(10) copper, silver, and gold. Inorg Chem. 2007 Aug 6;46(16):6218-20. Epub 2007 Jul 14. PubMed PMID: 17630731.
8: Killoran J, O'Shea DF. Impact of a conformationally restricted receptor on the BF2 chelated azadipyrromethene fluorosensing platform. Chem Commun (Camb). 2006 Apr 14;(14):1503-5. Epub 2006 Feb 27. PubMed PMID: 16575441.
9: Hall MJ, Allen LT, O'Shea DF. PET modulated fluorescent sensing from the BF2 chelated azadipyrromethene platform. Org Biomol Chem. 2006 Mar 7;4(5):776-80. Epub 2006 Jan 19. PubMed PMID: 16493459.
| Chemical | |
|---|---|
| CAS Num | 490035-90-0 |
| Chemical Formula | C34H24BBr2F2N3O2 |
| Molecular Weight | 715.19 |
| IUPAC Chemical Name | 2,8-dibromo-5,5-difluoro-3,7-bis(4-methoxyphenyl)-1,9-diphenyl-5H-dipyrrolo[1,2-c |
| Exact Mass | 713.02964 |
| Elemental Analysis | C, 57.10; H, 3.38; B, 1.51; Br, 22.34; F, 5.31; N, 5.88; O, 4.47 |
| Synonym | Azadipyrromethane ADPM06; ADPM 06; ADPM-06. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | COC1=CC=C(C2=C(Br)C(C3=CC=CC=C3)=C(N2[B-]4(F)F)N=C5[N+]4=C(C6=CC=C(OC)C=C6)C(Br)=C5C7=CC=CC=C7)C=C1 |
| Biological | |
| Targets and Effects | NA |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >2 years if stored properly |
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