Abstract
BODIPYs are photosensitizers activatable by light to generate highly reactive singlet oxygen (1O2) from molecular oxygen, leading to tissue damage in the photoirradiated region. Despite their extraordinary photophysical characteristics, they are not featured in clinical photodynamic therapy. This review discusses the recent advances in the design and/or modifications of BODIPYs since 2013, to improve their potential in photodynamic cancer therapy and related areas.
Similar content being viewed by others
References
A. Kamkaew, S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung and K. Burgess, Chem. Soc. Rev., 2013, 42, 77–88.
S. G. Awuah and Y. You, RSCAdv., 2012, 2, 11169–11183.
B. Kim, B. Sui, X. Yue, S. Tang, M. G. Tichy and K. D. Belfield, Eur. J. Org. Chem., 2017, 2017, 25–28.
J. Zou, Z. Yin, K. Ding, Q. Tang, J. Li, W. Si, J. Shao, Q. Zhang, W. Huang and X. Dong, ACS Appl. Mater. Interfaces, 2017, 9, 32475–32481.
J. Wang, Y. Hou, W. Lei, Q. Zhou, C. Li, B. Zhang and X. Wang, ChemPhysChem, 2012, 13, 2739–2747.
Y. Yang, Q. Guo, H. Chen, Z. Zhou, Z. Guo and Z. Shen, ChemComm, 2013, 49, 3940–3942.
Y. Chen, J. Zhao, L. Xie, H. Guo and Q. Li, RSC Adv., 2012, 2, 3942–3953.
R. Lincoln, A. M. Durantini, L. E. Greene, S. R. Martinez, R. Knox, M. C. Becerra and G. Cosa, Photochem. Photobiol. Sci., 2017, 16, 178–184.
M. Pawlicki, H. A. Collins, R. G. Denning and H. L. Anderson, Angew. Chem., Int. Ed., 2009, 48, 3244–3266.
Y. Shen, A. J. Shuhendler, D. Ye, J.-J. Xu and H.-Y. Chen, Chem. Soc. Rev., 2016, 45, 6725–6741.
T. Zhang, R. Lan, L. Gong, B. Wu, Y. Wang, D. W. J. Kwong, W.-K. Wong, K.-L. Wong and D. Xing, ChemBioChem, 2015, 16, 2357–2364.
R. L. Watley, S. G. Awuah, M. Bio, R. Cantu, H. B. Gobeze, V. N. Nesterov, S. K. Das, F. D’Souza and Y. You, Chem. - Asian J., 2015, 10, 1335–1343.
X. F. Zhang and N. Feng, Chem.- Asian J., 2017, 12, 2447–2456.
Y.-C. Lai, S.-Y. Su and C.-C. Chang, ACS Appl. Mater. Interfaces, 2013, 5, 12935–12943.
N. Epelde-Elezcano, E. Palao, H. Manzano, A. Prieto-Castaneda, A. R. Agarrabeitia, A. Tabero, A. Villanueva, S. de la Moya, I. Lopez-Arbeloa, V. Martinez-Martinez and M. J. Ortiz, Chemistry, 2017, 23, 4837–4848.
X. Cui, J. Zhao, Z. Mohmood and C. Zhang, Chem. Rec., 2016, 16, 173–188.
Y. You and W. Nam, Chem. Soc. Rev., 2012, 41, 7061–7084.
P. Majumdar, X. Yuan, S. Li, B. Le Guennic, J. Ma, C. Zhang, D. Jacquemind and J. Zhao, J. Mater. Chem. B, 2014, 2, 2838–2854.
E. Palao, R. Sola-Llano, A. Tabero, H. Manzano, A. R. Agarrabeitia, A. Villanueva, I. Lopez-Arbeloa, V. Martinez-Martinez and M. J. Ortiz, Chemistry, 2017, 23, 10139–10147.
L. Tabrizi and H. Chiniforoshan, RSC Adv., 2017, 7, 34160–34169.
Y. Liu, N. Song, L. Chen and Z. G. Xie, Chin. J. Polym. Sci., 2018, 36, 417–424.
K. D. Mjos and C. Orvig, Chem. Rev., 2014, 114, 4540–4563.
C. Mari, V. Pierroz, S. Ferrari and G. Gasser, Chem. Sci., 2015, 6, 2660–2686.
T. Wang, Y. Hou, Y. Chen, K. Li, X. Cheng, Q. Zhou and X. Wang, Dalton Trans., 2015, 44, 12726–12734.
J. Chalissery, D. Jalal, Z. Al-Natour and A. H. Hassan, DNA Repair, 2017, 51, 2–13.
A. Bhattacharyya, A. Dixit, K. Mitra, S. Banerjee, A. A. Karande and A. R. Chakravarty, Med. Chem. Commun., 2015, 6, 846–851.
N. Mukherjee, S. Podder, K. Mitra, S. Majumdar, D. Nandi and A. R. Chakravarty, Dalton Trans., 2018, 47, 823–835.
U. Bhattacharyya, B. Kumar, A. Garai, A. Bhattacharyya, A. Kumar, S. Banerjee, P. Kondaiah and A. R. Chakravarty, Inorg. Chem., 2017, 56, 12457–12468.
K. Mitra, S. Gautam, P. Kondaiah and A. R. Chakravarty, ChemMedChem, 2016, 11, 1956–1967.
M. K. Raza, S. Gautam, A. Garai, K. Mitra, P. Kondaiah and A. R. Chakravarty, Inorg. Chem., 2017, 56, 11019–11029.
Y. Liu, Z. Li, L. Chen and Z. Xie, Dyes Pigm., 2017, 141, 5–12.
M. Ucuncu, E. Karakus, E. Kurulgan Demirci, M. Sayar, S. Dartar and M. Emrullahoglu, Org. Lett., 2017, 19, 2522–2525.
C. S. Kue, A. Kamkaew, K. Burgess, L. V. Kiew, L. Y. Chung and H. B. Lee, Med. Res. Rev., 2016, 36, 494–575.
A. Kamkaew and K. Burgess, J. Med. Chem., 2013, 56, 7608–7614.
C. S. Kue, A. Kamkaew, H. B. Lee, L. Y. Chung, L. V. Kiew and K. Burgess, Mol. Pharm., 2015, 12, 212–222.
C. S. Kue, A. Kamkaew, S. H. Voon, L. V. Kiew, L. Y. Chung, K. Burgess and H. B. Lee, Sci. Rep., 2016, 6, 37209.
N. Zhao, T. M. Williams, Z. Zhou, F. R. Fronczek, M. Sibrian-Vazquez, S. D. Jois and M. G. H. Vicente, Bioconjugate Chem., 2017, 28, 1566–1579.
C. A. Puckett and J. K. Barton, Bioorg. Med. Chem., 2010, 18, 3564–3569.
P. Verwilst, C. C. David, V. Leen, J. Hofkens, P. A. de Witte and W. M. De Borggraeve, Bioorg. Med. Chem. Lett., 2013, 23, 3204–3207.
J. Gruenberg and H. Stenmark, Nat. Rev. Mol. Cell Biol., 2004, 5, 317–323.
M. Li, R. Tian, J. Fan, J. Du, S. Long and X. Peng, Dyes Pigm., 2017, 147, 99–105.
N. Shivran, M. Tyagi, S. Mula, P. Gupta, B. Saha, B. S. Patro and S. Chattopadhyay, Eur. J. Med. Chem., 2016, 122, 352–365.
Z. Lu, X. Zhang, Z. Wu, T. Zhai, Y. Xue, L. Mei and C. Li, RSCAdv., 2014, 4, 19495–19501.
X. J. Jiang, J. T. Lau, Q. Wang, D. K. Ng and P. C. Lo, Chemistry, 2016, 22, 8273–8281.
M. P. Gamcsik, M. S. Kasibhatla, S. D. Teeter and O. M. Colvin, Biomarkers, 2012, 17, 671–691.
I. S. Turan, F. P. Cakmak, D. C. Yildirim, R. Cetin-Atalay and E. U. Akkaya, Chemistry, 2014, 20, 16088–16092.
I. S. Turan, D. Yildiz, A. Turksoy, G. Gunaydin and E. U. Akkaya, Angew. Chem., Int. Ed., 2016, 55, 2875–2878.
I. S. Turan, G. Gunaydin, S. Ayan and E. U. Akkaya, Nat. Commun., 2018, 9, 805.
S. H. Voon, L. V. Kiew, H. B. Lee, S. H. Lim, M. I. Noordin, A. Kamkaew, K. Burgess and L. Y. Chung, Small, 2014, 10, 4993–5013.
Z. Guo, Y. Zou, H. He, J. Rao, S. Ji, X. Cui, H. Ke, Y. Deng, H. Yang, C. Chen, Y. Zhao and H. Chen, Adv. Mater., 2016, 28, 10155–10164.
Z. Wang, X. Hong, S. Zong, C. Tang, Y. Cui and Q. Zheng, Sci. Rep., 2015, 5, 12602.
W. Wang, L. Wang, Z. Li and Z. Xie, ChemComm, 2016, 52, 5402–5405.
Q. Zhang, Y. Cai, Q. Y. Li, L. N. Hao, Z. Ma, X. J. Wang and J. Yin, Chemistry, 2017, 23, 14307–14315.
Q. Zhang, Y. Cai, X.-J. Wang, J.-L. Xu, Z. Ye, S. Wang, P. H. Seeberger and J. Yin, ACS Appl. Mater. Interfaces, 2016, 8, 33405–33411.
W. Hu, H. Ma, B. Hou, H. Zhao, Y. Ji, R. Jiang, X. Hu, X. Lu, L. Zhang, Y. Tang, Q. Fan and W. Huang, ACS Appl. Mater. Interfaces, 2016, 8, 12039–12047.
S. H. Voon, S. X. Tiew, C. S. Kue, H. B. Lee, L. V. Kiew, M. Misran, A. Kamkaew, K. Burgess and L. Y. Chung, J. Biomed. Nanotechnol., 2016, 12, 1431–1452.
L. Liu, L. Fu, T. Jing, Z. Ruan and L. Yan, ACS Appl. Mater. Interfaces, 2016, 8, 8980–8990.
Y. Lv, L. Hao, W. Hu, Y. Ran, Y. Bai and L. Zhang, Sci. Rep., 2016, 6, 29321.
L. B. Meng, W. Zhang, D. Li, Y. Li, X. Y. Hu, L. Wang and G. Li, ChemComm, 2015, 51, 14381–14384.
D. Chen, Q. Tang, J. Zou, X. Yang, W. Huang, Q. Zhang, J. Shao and X. Dong, Adv. Healthcare Mater., 2018, e1701272.
L. Liu, Z. Ruan, T. Li, P. Yuan and L. Yan, Biomater. Sci., 2016, 4, 1638–1645.
X.-L. Xu, J. Shao, Q.-Y. Chen, C.-H. Li, M.-Y. Kong, F. Fang, L. Ji, D. Boison, T. Huang, J. Gao and C.-J. Feng, J. Inorg. Biochem., 2016, 159, 1–6.
Acknowledgments
This research study was supported by Postgraduate Research Grant (PPP) — Research, project no. PG222-2016A.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Kue, C.S., Ng, S.Y., Voon, S.H. et al. Recent strategies to improve boron dipyrromethene (BODIPY) for photodynamic cancer therapy: an updated review. Photochem Photobiol Sci 17, 1691–1708 (2018). https://doi.org/10.1039/c8pp00113h
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/c8pp00113h