|
|
A general approach to the design of high-performance near-infrared (NIR) D-π-A type fluorescent dyes |
Xiao Luoa, Jin Lib, Jie Zhaob, Luyan Gub, Xuhong Qiana,b, Youjun Yangb |
a School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China;
b State Key Laboratory of Bioreactor Engineering, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China |
|
|
Guide A four-step method is presented as a general guideline for design of high performance NIR absorbing/emitting dyes. |
|
Abstract Near infrared (NIR) absorbing and emitting dyes are sought after for their potentials in bioimaging and theranostic applications. They are typically not as stable as dyes absorbing and emitting in the visible spectral range, as the result of a reduced HOMO-LUMO band-gap. Also, they are not as efficient fluorescence emitters due to accelerated internal conversion kinetics. In addition, their large conjugative backbone render them high tendency to form aggregate and low aqueous solubility. In this tutorial, we have described a four-step approach for rational design of organic dyes with an overall high-performance to meet the rigorous requirements of biological applications. Also, some background regarding "NIR" is provided along with some recent breakthroughs of the field.
|
Received: 28 January 2019
|
Fund:The work is supported by the National Natural Science Foundation of China (Nos. 21574039 and 21822805) and Shanghai Municipal Science and Technology Commission (No. 18DZ1112703). |
|
|
|
[1] |
J.V. Frangioni, Curr. Opin. Chem. Biol. 7(2003) 626-634.
|
[2] |
Q.T. Nguyen, E.S. Olson, T.A. Aguilera, et al., Proc. Natl. Acad. Sci. U. S. A. 107(2010) 4317-4322.
|
[3] |
A.W. Czarnik, Chem. Biol. 2(1995) 423-428.
|
[4] |
E. Haustein, P. Schwille, HFSP J. 1(2007) 169-180.
|
[5] |
J. Mei, Y. Huang, H. Tian, ACS Appl. Mater. Interfaces 10(2018) 12217-12261.
|
[6] |
R. Weissleder, Science 312(2006) 1168-1171.
|
[7] |
M. Rudin, R. Weissleder, Nat. Rev. Drug Disc. 2(2003) 123-131.
|
[8] |
K. Pap, S. Plehati, I. Rajkovi c, D. ?igman, International Design Conference-Design, (2010), pp. 1857-1862.
|
[9] |
BSI ISO 20473:2007 Optics and Photonics. Spectral Bands, British Standards Institution (BSI) and International Organization for Standardisation (ISO), 2007 checked 2015.
|
[10] |
C.M. Lin, S.M. Usama, K. Burgess, Molecules 23(2018) 2900.
|
[11] |
M. Manley, Chem. Soc. Rev. 43(2014) 8200-8214.
|
[12] |
M. Kamper, H. Ta, N.A. Jensen, S.W. Hell, S. Jakobs, Nat. Commun. 9(2018) 4762.
|
[13] |
Z.H. Lei, X.R. Li, X. Luo, et al., Angew. Chem. Int. Ed. 56(2017) 2979-2983.
|
[14] |
Z.Y. Wang, Near-Infrared Organic Materials and Emerging Applications, CRC Press, New York, 2013.
|
[15] |
J.R. Hou, D. Jin, B. Chen, L.L. Si, Y. Li, Chin. Chem. Lett. 28(2017) 1875-1877.
|
[16] |
M.S. Lin, B.A. Rasco, A.G. Cavinato, M. Al-Holy, Infrared Spectroscopy for Food Quality Analysis and Control, Elsevier Publishing, Burlington, MA, USA, 2009.
|
[17] |
B.A. Kairdolf, A.M. Smith, T.H. Stokes, et al., Annu. Rev. Anal. Chem. 6(2013) 143-162.
|
[18] |
J. Qian, B.Z. Tang, Chemisty 3(2017) 56-91.
|
[19] |
Z.Q. Guo, S. Park, J. Yoon, I. Shin, Chem. Soc. Rev. 43(2014) 16-29.
|
[20] |
K.Y. Zhang, Q. Yu, H.J. Wei, et al., Chem. Rev. 118(2018) 1770-1839.
|
[21] |
R. Weissleder, M.J. Pittet, Nature 452(2008) 580-589.
|
[22] |
J. Zhang, R.E. Campbell, A.Y. Ting, et al., Nat. Rev. Mol. Cell Biol. 3(2002) 906-918.
|
[23] |
W.R. Zipfel, R.M. Williams, W.W. Webb, Nat. Biotechnol. 21(2003) 1369-1377.
|
[24] |
B. Huang, M. Bates, X.W. Zhuang, Annu. Rev. Biochem. 78(2009) 993-1016.
|
[25] |
V. Ntziachristos, Annu. Rev. Biomed. Eng. 8(2006) 1-33.
|
[26] |
D.W. Domaille, E.L. Que, C.J. Chang, Nat. Chem. Biol. 4(2008) 168-175.
|
[27] |
J.H. Rao, A. Dragulescu-Andrasi, H.Q. Yao, Curr. Opin. Biotechnol. 18(2007) 17-25.
|
[28] |
S.L. Luo, E.L. Zhang, Y.P. Su, T.M. Cheng, C.M. Shi, Biomaterials 32(2011) 7127-7138.
|
[29] |
E.A. Specht, E. Braselmann, A.E. Palmer, Ann. Rev. Physiol. 79(2017) 93-117.
|
[30] |
S.L. Jacques, Phys. Med. Biol. 58(2013) R37-R61.
|
[31] |
L.Y. Shi, L.A. Sordillo, A. Rodríguez-Contreras, R. Alfano, J. Biophotonics 9(2016) 38-43.
|
[32] |
Z.P. Qin, J.C. Bischof, Chem. Soc. Rev. 41(2012) 1191-1217.
|
[33] |
K. Welsher, Z. Liu, S.P. Sherlock, et al., Nat. Nanotechnol. 4(2009) 773-780.
|
[34] |
P.Y. Wang, Y. Fan, L.F. Lu, et al., Nat. Commun. 9(2018) 2898.
|
[35] |
J.Y. Zhao, D. Zhong, S.B. Zhou, Mater. Chem. B 6(2018) 349-365.
|
[36] |
A.L. Antaris, H. Chen, K. Cheng, et al., Nat. Mater. 15(2016) 235-242.
|
[37] |
S. Zhu, Z. Hu, R. Tian, et al., Adv. Mater. 30(2018) 1802546.
|
[38] |
V.J. Pansare, S. Hejazi, W.J. Faenza, R.K. Prud'homme, Chem. Mater. 24(2012) 812-827.
|
[39] |
E. Hemmer, A. Benayas, F. Légaré, F. Vetrone, Nanoscale Horiz. 1(2016) 168-184.
|
[40] |
J. Gao, X. Chen, Z. Cheng, Curr. Top Med. Chem. 10(2010) 1147-1157.
|
[41] |
G. Qian, Z.Y. Wang, Chem. Asian J. 5(2010) 1006-1029.
|
[42] |
M. Baloban, D.M. Shcherbakova, S. Pletnev, et al., Chem. Sci. 8(2017) 4546-4557.
|
[43] |
J. Piccard, Ber. Dtsch. Chem. Ges. 46(1913) 1843-1860.
|
[44] |
A. Mishra, R.K. Behera, P.K. Behera, B.K. Mishra, G.B. Behera, Chem. Rev. 100(2000) 1973-2012.
|
[45] |
S. Daehne, Ute. Resch-Genger, O.S. Wolfbeis, Near-Infrared Dyes for High Technology Applications, Springer Science & Business Media, Berlin/Heidelberg, Germany, 2012.
|
[46] |
J. Yao, M. Yang, Y.X. Duan, Chem. Rev. 114(2014) 6130-6178.
|
[47] |
M.V. Marshall, J.C. Rasmussen, I. Tan, et al., Open Surg. Oncol. J. 2(2010) 12-25.
|
[48] |
I.J. Fox, E.H. Wood, Proc. Staff Meet. Mayo Clin. 35(1960) 732-744.
|
[49] |
Z. Starosolski, R. Bhavane, K.B. Ghaghada, et al., PLoS One 12(2017) e0187563.
|
[50] |
J.T. Alander, I. Kaartinen, A. Laakso, et al., Int. J. Biomed. Imaging 2012(2012) 940585.
|
[51] |
M.L. Landsman, G. Kwant, G.A. Mook, W.G. Zijlstra, J. Appl. Physiol. 40(1976) 575-583.
|
[52] |
W. Holzer, M. Mauerer, A. Penzkofer, et al., J. Photochem. Photobiol. B Biol. 47(1998) 155-164.
|
[53] |
S. Yoneya, T. Saito, Y. Komatsu, et al., Invest. Ophthalmol. Visual Sci. 39(1998) 1286-1290.
|
[54] |
E. Engel, T. Schraml, T. Maisch, et al., Invest. Ophthalmol. Visual Sci. 49(2008) 1777-1783.
|
[55] |
D.H. Oushiki, H. Kojima, T. Terai, et al., J. Am. Chem. Soc. 132(2010) 2795-2801.
|
[56] |
W. Sun, S.G. Guo, C. Hu, J.L. Fan, X.J. Peng, Chem. Rev. 116(2016) 7768-7817.
|
[57] |
M.T. Sun, H. Yu, H.J. Zhu, et al., Anal. Chem. 86(2014) 671-677.
|
[58] |
K. Kundu, S.F. Knight, N. Willett, et al., Angew. Chem. Int. Ed. 48(2009) 299-303.
|
[59] |
X.T. Jia, Q.Q. Chen, Y.F. Yang, et al., J. Am. Chem. Soc.138(2016) 10778-10781.
|
[60] |
G.T. Dempsey, M. Bates, W.E. Kowtoniuk, et al., J. Am. Chem. Soc. 131(2009) 18192-18193.
|
[61] |
H. Niu, X. Jiang, J. He, et al., Tetrahedron Lett. 50(2009) 6668-6671.
|
[62] |
L. Yuan, W.Y. Lin, K.B. Zheng, L.W. He, W.M. Huang, Chem. Soc. Rev. 42(2013) 622-661.
|
[63] |
M.Y. Li, P.C. Cui, K. Li, et al., Chin. Chem. Lett. 29(2018) 992-994.
|
[64] |
Y. Yang, H. Wang, Y.L. Wei, et al., Chin. Chem. Lett. 28(2017) 2023-2026.
|
[65] |
S. Dähne, Science 199(1978) 1163-1167.
|
[66] |
J. Griffiths, Colour and Constitution of Organic Molecules, Academic Press, London, 1976.
|
[67] |
R.L.M. Allen, Colour Chemistry, 1st ed., Appleton-Century-Crofts, New York, 1971.
|
[68] |
J. Clayden, N. Greeves, S. Warren, Organic Chemistry, 2nd ed., Oxford University Press, 2001.
|
[69] |
R.L. Christensen, A. Faksh, J.A. Meyers, et al., J. Phys. Chem. A 108(2004) 8229-8236.
|
[70] |
J. Rissler, Chem. Phys. Lett. 395(2004) 92-96.
|
[71] |
C.B. Gorman, E.J. Ginsburg, S.R. Marder, R.H. Grubbs, Angew. Chem. Int. Ed. 28(1989) 1571-1574.
|
[72] |
K. Mullen, G. Wegner, Electronic Materials:The Oligomer Approach, WileyVCH, Berlin, 1998.
|
[73] |
R. Duval, C. Duplaisb, Nat. Prod. Rep. 34(2017) 161-193.
|
[74] |
W.P. Chen, R.F. Chen, Q.P. Liu, Y. He, K. He, Chem. Sci. 8(2017) 4917-4925.
|
[75] |
J.M. Gao, S.X. Yang, J.C. Qin, Chem. Rev. 113(2013) 4755-4811.
|
[76] |
J. Bendig, U. Schedler, T. Harder, et al., J. Photochem. Photobiol. A 91(1995) 53-57.
|
[77] |
S.A. Tikhonov, V.I. Vovna, N.A. Gelfand, et al., J. Phys. Chem. A 120(2016) 7361-7369.
|
[78] |
A. Chaudhuri, Y. Venkatesh, K.K. Behara, N.D.P. Singh, Org. Lett. 19(2017) 1598-1601.
|
[79] |
S. Imazeki, A. Mukoh, T. Yoneyama, M. Kaneko, Mol. Cryst. Liq. Cryst. 145(1987) 79-93.
|
[80] |
Y.M. Shen, Z.H. Shang, Y.H. Yang, et al., J. Org. Chem. 80(2015) 5906-5911.
|
[81] |
Y. Xiao, F.Y. Liu, Z. Chen, et al., Chem. Commun. 51(2015) 6480-6488.
|
[82] |
A. Treibs, K. Jacob, Justus Liebigs Ann. Chem. 699(1966) 153-167.
|
[83] |
A. Schmitt, B. Hinkeldey, M. Wild, G. Jung, J. Fluoresc. 19(2009) 755-758.
|
[84] |
M.Y. Fu, Y. Xiao, X.H. Qian, D.F. Zhao, Y.F. Xu, Chem. Commun.15(2008) 1780-1782.
|
[85] |
G. Sathyamoorthi, M.L. Soong, T.W. Ross, J.H. Boyer, Heteroat. Chem. 4(1993) 603-608.
|
[86] |
A.K.-Y. Jen, Y.Q. Liu, L.X. Zheng, et al., Adv. Mater. 11(1999) 452-455.
|
[87] |
Y.Y. Cheng, G.C. Li, Y. Liu, et al., J. Am. Chem. Soc. 138(2016) 4730-4738.
|
[88] |
W.M. Liu, B.J. Zhou, G. Niu, et al., ACS Appl. Mater. Interfaces 7(2015) 7421-7427.
|
[89] |
L. Yuan, W.Y. Lin, Y.T. Yang, H. Chen, J. Am. Chem. Soc. 134(2012) 1200-1211.
|
[90] |
M. Sibrian-Vazquez, J.O. Escobedo, M. Lowry, R.M. Strongin, Pure Appl. Chem. 84(2012) 2443-2456.
|
[91] |
E. Azuma, N. Nakamura, K. Kuramochi, et al., J. Org. Chem. 77(2012) 3492-3500.
|
[92] |
A.B. Descalzo, K. Rurack, Chem. Eur. J. 15(2009) 3173-3185.
|
[93] |
R.S. Lepkowicz, C.M. Cirloganu, O.V. Przhonska, et al., Chem. Phys. 306(2004) 171-183.
|
[94] |
A. Treibs, K. Jacob, Angew. Chem. Int. Ed. 4(1965) 694-694.
|
[95] |
X.Z. Song, J.W. Foley, Dyes Pigm. 78(2008) 60-64.
|
[96] |
B.H. Li, L.F. Lu, M.Y. Zhao, Z.H. Lei, F. Zhang, Angew. Chem. Int. Ed. 57(2018) 7483-7487.
|
[97] |
B.L. Guennic, D. Jacquemin, Acc. Chem. Res. 48(2015) 530-537.
|
[98] |
K.Z. Gu, Y.S. Xu, H. Li, et al., J. Am. Chem. Soc. 138(2016) 5334-5340.
|
[99] |
N. Karton-Lifshin, L. Albertazzi, M. Bendikov, et al., J. Am. Chem. Soc. 134(2012) 20412-20420.
|
[100] |
H.Y. Li, X.H. Li, W. Shi, Y.H. Xu, H.M. Ma, Angew. Chem. Int. Ed. 57(2018) 12830-12834.
|
[101] |
L. Strekowski, Heterocyclic Polymethine Dyes:Synthesis, Properties and Applications, Springer-Verlag, Berlin, 2008.
|
[102] |
K. Umezawa, Y. Nakamura, H. Makino, D. Citterio, K. Suzuki, J. Am. Chem. Soc. 130(2008) 1550-1551.
|
[103] |
M. Irie, Chem. Rev. 100(2000) 1685-1716.
|
[104] |
G.L. Niu, W.M. Liu, B.J. Zhou, et al., J. Org. Chem. 81(2016) 7393-7399.
|
[105] |
D. Wu, Y.Z. Shen, J.H. Chen, et al., Chin. Chem. Lett. 28(2017) 1979-1982.
|
[106] |
F.L. Song, R. Liang, J.D. Deng, Z.W. Liu, X.J. Peng, Chin. Chem. Lett. 28(2017) 1997-2000.
|
[107] |
Z.H. Lei, Z.H. Zeng, X.H. Qian, Y.J. Yang, Chin. Chem. Lett. 28(2017) 2001-2004.
|
[108] |
P. Ning, W.J. Wang, M. Chen, Y. Feng, X.M. Meng 28(2017) 1943-1951.
|
[109] |
X.T. Jia, Q.Q. Chen, Y.F. Yang, et al., J. Am. Chem. Soc.138(2016) 10778-10781.
|
[110] |
A.P. Gorka, R.R. Nani, J.J. Zhu, S. Mackem, M.J. Schnermann, J. Am. Chem. Soc. 136(2014) 14153-14159.
|
[111] |
X. Jing, C. He, L. Zhao, C.Y. Duan, Acc. Chem. Res. 52(2019) 100-109.
|
[112] |
S.Y. Hsueh, C.C. Lai, Y.H. Liu, et al., Org. Lett. 9(2007) 4523-4526.
|
[113] |
A.G. Cheetham, T.D.W. Claridge, H.L. Anderson, Org. Biomol. Chem. 5(2007) 457-462.
|
[114] |
E.J.F. Klotz, T.D.W. Claridge, H.L. Anderson, J. Am. Chem. Soc. 128(2006) 15374-15375.
|
[115] |
E. Arunkumar, C.C. Forbes, B.C. Noll, B.D. Smith, J. Am. Chem. Soc. 127(2005) 3288-3289.
|
[116] |
Z.M. Tao, G.S. Hong, C. Shinji, et al., Angew. Chem. Int. Ed. 125(2013) 13240-13244.
|
[117] |
S. Hecht, J.M.J. Frechet, Angew. Chem. Int. Ed. 40(2001) 74-91.
|
[118] |
K. Yanagi, K. Iakoubovskii, H. Matsui, et al., J. Am. Chem. Soc. 129(2007) 4992-4997.
|
[119] |
X.M. Wu, S. Chang, X.R. Sun, Chem. Sci. 4(2013) 1221-1228.
|
[120] |
J.E.H. Buston, J.R. Young, H.L. Anderson, Chem. Commun.11(2000) 905-906.
|
[121] |
M. Cooper, A. Ebner, M. Briggs, et al., J. Fluoresc. 14(2004) 145-150.
|
[122] |
C.Y. Fan, J.C. Hsiang, R.M. Dickson, ChemPhysChem 13(2012) 1023-1029.
|
[123] |
B. Li, Z. He, H. Zhou, H. Zhang, T. Cheng, Chin. Chem. Lett. 28(2017) 1929-1934.
|
[124] |
J.L. Bricks, A.D. Kachkovskii, Y.L. Slominskii, A.O. Gerasov, S.V. Popov, Dyes Pigm. 121(2015) 238-255.
|
[125] |
M.S. Michie, R. Götz, C. Franke, et al., J. Am. Chem. Soc. 139(2017) 12406-12409.
|
[126] |
M.L. Korb, Y.E. Hartman, J. Kovar, et al., J. Surg. Res. 188(2014) 119-128.
|
[127] |
A. Baeyer, Ber. Dtsch. Chem. Ges. 4(1871) 555-558.
|
[128] |
Y.J. Yang, M. Lowry, X.Y. Xu, et al., Proc. Natl. Acad. Sci. U. S. A. 105(2008) 8829-8834.
|
[129] |
J.B. Grimm, A.J. Sung, W.R. Legant, et al., ACS Chem. Biol. 8(2013) 1303-1310.
|
[130] |
T. Egawa, Y. Koide, K. Hanaoka, et al., Chem. Commun. 47(2011) 4162-4164.
|
[131] |
A. Fukazawa, S. Suda, M. Taki, et al., Chem. Commun. 52(2016) 1120-1123.
|
[132] |
J.B. Grimm, B.P. English, J.J. Chen, et al., Nat. Methods 12(2015) 244-250.
|
[133] |
L. Wu, K. Burgess, Org. Lett. 10(2008) 1779-1782.
|
[134] |
Y. Koide, Y. Urano, K. Hanaoka, T. Terai, T. Nagano, ACS Chem. Biol. 6(2011) 600-608.
|
[135] |
C. Aaron, C.C. Barker, J. Chem. Soc. (1963) 2655-2662.
|
[136] |
X.Q. Zhou, R. Lai, J.R. Beck, H. Li, C.I. Stains, Chem. Commun. 52(2016) 12290-12293.
|
[137] |
J. Liu, Y.Q. Sun, H.X. Zhang, et al., ACS Appl. Mater. Interfaces 8(2016) 22953-22962.
|
[138] |
M. Sauer, K.T. Han, R. Muller, et al., J. Fluoresc. 5(1995) 247-261.
|
[139] |
M. Sauer, K.T. Han, R. Muller, et al., J. Fluoresc. 3(1993) 131-139.
|
[140] |
O.O. Abugo, R. Nair, J.R. Lakowicz, Anal. Biochem. 279(2000) 142-150.
|
[141] |
A.V. Anzalone, T.Y. Wang, Z.X. Chen, V.W. Cornish, Angew. Chem. Int. Ed. 52(2013) 650-654.
|
[142] |
J. Arden-Jacob, J. Frantzeskos, N.U. Kemnitzer, A. Zilles, K.H. Drexhage, Spectrochimica Acta Part A 57(2001) 2271-2283.
|
|
|
|