Citation: Ying Xu, Chengying Shen, Hailong Yuan, Wei Wu. Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting[J]. Chinese Chemical Letters, ;2024, 35(9): 109324. doi: 10.1016/j.cclet.2023.109324 shu

Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting

Ying Xu ^{a, 1} ,
Chengying Shen ^{c, d, 1} ,
Hailong Yuan ^c ,
Wei Wu ^{a, b, *,}

a.
Key Laboratory of Smart Drug Delivery of MOE, School of Pharmacy, Fudan University, Shanghai 201203, China
b.
Center for Medical Research and Innovation, Shanghai Pudong Hospital, Fudan University Pudong Medical Center, Shanghai 201399, China
c.
Department of Pharmacy, Air Force Medical Center, PLA, Beijing 100142, China
d.
Jiangxi Provincial People's Hospital, The First Affiliated Hospital of Nanchang Medical College, Nanchang 330006, China

wuwei@shmu.edu.cn

Received Date: 8 October 2023
Revised Date: 10 November 2023
Accepted Date: 15 November 2023
Available Online: 19 November 2023

Figures(6)

The microphases and miscibility in binary curcumin (Cur) solid dispersions (SDs) with amorphous polyvinylpyrrolidone K30 (PVP K30) and semi-crystalline poloxamer (P407) and poly(ethylene glycol) 6000 (PEG6000) as carriers were investigated by fluorescence contrasting utilizing confocal laser scanning microscopy. A super sensitive fluorophore P4 with typical aggregation-caused quenching properties was employed to stain the continuous polymer phases and contrasted with the autofluorescence of the model drug Cur. In addition, differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD) were utilized to assist in explanation of the fluorescence results. In all three SD systems, there is always a homogenous polymer phase stained by P4 and it is difficult to adulterate Cur crystals by P4. Cur-enriched rather than polymer-enriched domains could be detected. In the Cur-PVP K30 system, Cur exists in an amorphous form at a Cur loading level of 50% and below, while Cur crystallines phase out and continuously grow with the increase of Cur loading from 60% to 90%. The phase behaviors in the Cur-P407 and Cur-PEG 6000 systems are similar but with minor differences. In both systems, Cur phases out as clusters of drug-enriched domains at a loading level of 20% and below, which however cannot be correlated with crystallization, as evidenced by both DSC and PXRD. There is a transition from an amorphous to a crystalline state from 20% to 30% Cur loading, above which Cur crystallines can be detected. It is interesting that a co-mix phase of both Cur- and PEG 6000-enriched domains can be identified at Cur loading levels of 10% and less. Taking together, it is concluded that contrasting Cur autofluorescence with the signals of P4 proves to be a functional strategy to reveal multiple phases in the binary SD systems investigated.
- Solid dispersion,
- Curcumin,
- PEG,
- PVP,
- Poloxamer,
- Fluorescence,
- Environment-responsive,
- Confocal laser scanning microscopy
1. [1]
  W.L. Chiou, S. Riegelman, J. Pharm. Sci. 60 (1971) 1281–1302. doi: 10.1002/jps.2600600902
2. [2]
  A.T. Serajuddin, J. Pharm. Sci. 88 (1999) 1058–1566. doi: 10.1021/js980403l
3. [3]
  C.L. Vo, C. Park, B.J. Lee, Eur. J. Pharm. Biopharm. 85 (2013) 799–813. doi: 10.1016/j.ejpb.2013.09.007
4. [4]
  S.V. Bhujbal, B. Mitra, U. Jain, et al., Acta Pharm. Sin. B 8 (2021) 2505–2536.
5. [5]
  Y. Kong, W. Wang, C. Wang, et al., Int. J. Pharm. 631 (2023) 122524. doi: 10.1016/j.ijpharm.2022.122524
6. [6]
  K. Sekiguchi, N. Obi, Chem. Pharm. Bull. 9 (1961) 866–872. doi: 10.1248/cpb.9.866
7. [7]
  A.G. Nambiar, M. Singh, A.R. Mali, et al., AAPS PharmSciTech 23 (2022) 249. doi: 10.1208/s12249-022-02408-4
8. [8]
  A. Butreddy, Eur. J. Pharm. Biopharm. 177 (2022) 289–307. doi: 10.1016/j.ejpb.2022.07.010
9. [9]
  F. Meng, U. Gala, H. Chauhan, Drug Dev. Ind. Pharm. 41 (2015) 1401–1415. doi: 10.3109/03639045.2015.1018274
10. [10]
  L.S. Taylor, G.G.Z. Zhang, Adv. Drug Deliv. Rev. 101 (2016) 122–142. doi: 10.1016/j.addr.2016.03.006
11. [11]
  T. Van Duong, G. Van den Mooter, Expert Opin. Drug Deliv. 13 (2016) 1681–1694. doi: 10.1080/17425247.2016.1198769
12. [12]
  K. DeBoyace, P.L.D. Wildfong, J. Pharm. Sci. 107 (2018) 57–74. doi: 10.1016/j.xphs.2017.03.029
13. [13]
  F. Qian, J. Huang, M.A. Hussain, J. Pharm. Sci. 99 (2010) 2941–2947. doi: 10.1002/jps.22074
14. [14]
  D.N. Bikiaris, Expert Opin. Drug Deliv. 8 (2011) 1501–1519. doi: 10.1517/17425247.2011.618181
15. [15]
  J. Qi, Y. Lu, W. Wu, Curr. Pharm. Des. 21 (2015) 2668–2676. doi: 10.2174/1381612821666150416100639
16. [16]
  F. Meng, V. Dave, H. Chauhan, Eur. J. Pharm. Sci. 77 (2015) 106–111. doi: 10.1016/j.ejps.2015.05.018
17. [17]
  S. Baghel, H. Cathcart, N.J. O'Reilly, J. Pharm. Sci. 105 (2016) 2527–2544. doi: 10.1016/j.xphs.2015.10.008
18. [18]
  D. Gramaglia, B.R. Conway, V.L. Kett, et al., Int. J. Pharm. 301 (2005) 1–5. doi: 10.1016/j.ijpharm.2005.04.038
19. [19]
  D. Lin, Y. Huang, Int. J. Pharm. 399 (2010) 109–115. doi: 10.1016/j.ijpharm.2010.08.013
20. [20]
  Y. Sun, J. Tao, G.G. Zhang, et al., J. Pharm. Sci. 99 (2010) 4023–4031. doi: 10.1002/jps.22251
21. [21]
  B. Tian, X. Wang, Y. Zhang, et al., Pharm. Res. 32 (2015) 840–851. doi: 10.1007/s11095-014-1500-6
22. [22]
  J.A. Baird, L.S. Taylor, Adv. Drug Deliv. Rev. 64 (2012) 396–421. doi: 10.1016/j.addr.2011.07.009
23. [23]
  Z. Chen, Z. Liu, F. Qian, Mol. Pharm. 12 (2015) 590–599. doi: 10.1021/mp500661v
24. [24]
  S. Baghel, H. Cathcart, N.J. O'Reilly, Eur. J. Pharm. Biopharm. 107 (2016) 16–31. doi: 10.1016/j.ejpb.2016.06.024
25. [25]
  S.G. Gumaste, S.S. Gupta, A.T.M. Serajuddin, AAPS J. 18 (2016) 1131–1143. doi: 10.1208/s12248-016-9939-5
26. [26]
  R. Jog, R. Gokhale, D.J. Burgess, Int. J. Pharm. 509 (2016) 285–295. doi: 10.1016/j.ijpharm.2016.05.068
27. [27]
  N. Li, L.S. Taylor, Mol. Pharm. 13 (2016) 1123–1136. doi: 10.1021/acs.molpharmaceut.5b00925
28. [28]
  H.S. Purohit, L.S. Taylor, Mol. Pharm. 12 (2015) 4542–4553. doi: 10.1021/acs.molpharmaceut.5b00761
29. [29]
  B. Tian, X. Tang, L.S. Taylor, Mol. Pharm. 13 (2016) 3988–4000. doi: 10.1021/acs.molpharmaceut.6b00803
30. [30]
  H.S. Purohit, J.D. Ormes, S. Saboo, et al., Pharm. Res. 34 (2017) 1364–1377. doi: 10.1007/s11095-017-2145-z
31. [31]
  R. Yang, G.G.Z. Zhang, K. Kjoller, et al., Int. J. Pharm. 619 (2022) 121708. doi: 10.1016/j.ijpharm.2022.121708
32. [32]
  R. Yang, G.G.Z. Zhang, D.Y. Zemlyanov, et al., J. Pharm. Sci. 112 (2023) 304–317. doi: 10.3390/agriculture13020304
33. [33]
  L.A. Wegiel, Y. Zhao, L.J. Mauer, et al., Pharm. Dev. Technol. 19 (2014) 976–986. doi: 10.3109/10837450.2013.846374
34. [34]
  X. Hu, J. Zhang, Z. Yu, et al., Nanomedicine 11 (2015) 1939–1948. doi: 10.1016/j.nano.2015.06.013
35. [35]
  X. Hu, W. Fan, Z. Yu, et al., Nanoscale 8 (2016) 7024–7035. doi: 10.1039/C5NR07474F
36. [36]
  Y. Cai, X. Ji, Y. Zhang, et al., Aggregate 4 (2023) e277. doi: 10.1002/agt2.277
37. [37]
  H. He, C. Liu, J. Ming, et al., Aggregate 3 (2022) e163. doi: 10.1002/agt2.163
38. [38]
  J. Qi, X. Hu, X. Dong, et al., Adv. Drug Deliv. Rev. 143 (2019) 206–225. doi: 10.1016/j.addr.2019.05.009
39. [39]
  X. Wang, L. Qiu, X. Wang, et al., Int. J. Pharm. 573 (2020) 118840. doi: 10.1016/j.ijpharm.2019.118840
40. [40]
  Y. Yang, Y. Lv, C. Shen, et al., Acta Pharm. Sin. B 11 (2021) 1056–1068. doi: 10.1016/j.apsb.2020.08.002
41. [41]
  Z. Huang, Y. Huang, W. Wang, et al., J. Control. Release 325 (2020) 206–222. doi: 10.1016/j.jconrel.2020.06.004
42. [42]
  I. Zoya, H. He, L. Wang, et al., Chin. Chem. Lett. 32 (2021) 1545–1549. doi: 10.1016/j.cclet.2020.09.038
43. [43]
  Y. Jiang, Y. Jiang, Z. Ding, et al., Int. J. Nanomed. 17 (2022) 3443–3456. doi: 10.2147/ijn.s369978
44. [44]
  L. Li, S. Chunta, X. Zheng, et al., Chin. Chem. Lett. 35 (2024) 108662. doi: 10.1016/j.cclet.2023.108662
45. [45]
  B. Shen, C. Shen, W. Zhu, et al., Acta Pharm. Sin. B 11 (2021) 978–988. doi: 10.1016/j.apsb.2021.02.015
46. [46]
  L. Hang, C. Shen, B. Shen, et al., Chin. Chem. Lett. 33 (2022) 4948–4951. doi: 10.1016/j.cclet.2022.03.108
47. [47]
  C. Shen, Y. Yang, B. Shen, et al., Nanoscale 10 (2017) 436–450. doi: 10.1109/EIT.2017.8053401
48. [48]
  Y. Xie, B. Shi, F. Xia, et al., J. Control. Release 270 (2018) 65–75. doi: 10.1016/j.jconrel.2017.11.046
49. [49]
  C.C.C. Teixeira, L.M. Mendonça, M.M. Bergamaschi, et al., AAPS PharmSciTech 17 (2016) 252–261. doi: 10.1208/s12249-015-0337-6
50. [50]
  H. McFall, S. Sarabu, V. Shankar, et al., Int. J. Pharm. 554 (2019) 302–311. doi: 10.1016/j.ijpharm.2018.11.005
51. [51]
  C. Muangnoi, P.R.N. Bhuket, P. Jithavech, et al., Pharmaceutics 11 (2019) 373. doi: 10.3390/pharmaceutics11080373
52. [52]
  R. Bajracharya, S.H. Lee, J.G. Song, et al., Pharmaceutics 11 (2019) 206. doi: 10.3390/pharmaceutics11050206
53. [53]
  X. Ji, Y. Cai, X. Dong, et al., Nanoscale 15 (2023) 9290–9296. doi: 10.1039/d3nr01018j
54. [54]
  S. Saboo, N.A. Mugheirbi, D.Y. Zemlyanov, et al., J. Control. Release 298 (2019) 68–82. doi: 10.1016/j.jconrel.2019.01.039
55. [55]
  S. Saboo, L.S. Taylor, Int. J. Pharm. 529 (2017) 654–666. doi: 10.1016/j.ijpharm.2017.07.034
56. [56]
  M.J. Jackson, S.J. Toth, U.S. Kestur, et al., Mol. Pharm. 11 (2014) 3027–3038. doi: 10.1021/mp500201s
57. [57]
  L.I. Mosquera-Giraldo, L.S. Taylor, Mol. Pharm. 12 (2015) 496–503. doi: 10.1021/mp500573z
58. [58]
  S.A. Raina, D.E. Alonzo, G.G. Zhang, et al., Pharm. Res. 32 (2015) 3660–3673. doi: 10.1007/s11095-015-1725-z
59. [59]
  M.J. Jackson, U.S. Kestur, M.A. Hussain, et al., Pharm. Res. 33 (2016) 1276–1288. doi: 10.1007/s11095-016-1871-y
60. [60]
  L. Lindfors, S. Forssén, J. Westergren, et al., J. Colloid. Interf. Sci. 325 (2008) 404–413. doi: 10.1016/j.jcis.2008.05.034
1. [1]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
2. [2]
  Kuan Deng , Fei Yang , Zhi-Qi Cheng , Bi-Wen Ren , Hua Liu , Jiao Chen , Meng-Yao She , Le Yu , Xiao-Gang Liu , Hai-Tao Feng , Jian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464
3. [3]
  Yuxin Li , Chengbin Liu , Qiuju Li , Shun Mao . Fluorescence analysis of antibiotics and antibiotic-resistance genes in the environment: A mini review. Chinese Chemical Letters, 2024, 35(10): 109541-. doi: 10.1016/j.cclet.2024.109541
4. [4]
  Rui Cheng , Xin Huang , Tingting Zhang , Jiazhuang Guo , Jian Yu , Su Chen . Solid superacid catalysts promote high-performance carbon dots with narrow-band fluorescence emission for luminescence solar concentrators. Chinese Chemical Letters, 2024, 35(8): 109278-. doi: 10.1016/j.cclet.2023.109278
5. [5]
  Wen Xiao , Fazhan Wang , Yangzhuo Gu , Xi He , Na Fan , Qian Zheng , Shugang Qin , Zhongshan He , Yuquan Wei , Xiangrong Song . PEG400-mediated nanocarriers improve the delivery and therapeutic efficiency of mRNA tumor vaccines. Chinese Chemical Letters, 2024, 35(5): 108755-. doi: 10.1016/j.cclet.2023.108755
6. [6]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
7. [7]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
8. [8]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
9. [9]
  Zhiqiang Liu , Qiang Gao , Wei Shen , Meifeng Xu , Yunxin Li , Weilin Hou , Hai-Wei Shi , Yaozuo Yuan , Erwin Adams , Hian Kee Lee , Sheng Tang . Removal and fluorescence detection of antibiotics from wastewater by layered double oxides/metal-organic frameworks with different topological configurations. Chinese Chemical Letters, 2024, 35(8): 109338-. doi: 10.1016/j.cclet.2023.109338
10. [10]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
11. [11]
  Zhichao Zhou , Fuqian Chen , Xiaotong Xia , Dong Ye , Rong Zhou , Lei Li , Tao Deng , Zhenhua Ding , Fang Liu . Developing a fluorescence substrate for HRP-based diagnostic assays with superiorities over the commercial ADHP. Chinese Chemical Letters, 2024, 35(6): 108970-. doi: 10.1016/j.cclet.2023.108970
12. [12]
  Zixi Zou , Jingyuan Wang , Yian Sun , Qian Wang , Da-Hui Qu . Controlling molecular assembly on time scale: Time-dependent multicolor fluorescence for information encryption. Chinese Chemical Letters, 2024, 35(7): 108972-. doi: 10.1016/j.cclet.2023.108972
13. [13]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
14. [14]
  Peide Zhu , Yangjia Liu , Yaoyao Tang , Siqi Zhu , Xinyang Liu , Lei Yin , Quan Liu , Zhiqiang Yu , Quan Xu , Dixian Luo , Juncheng Wang . Bi-doped carbon quantum dots functionalized liposomes with fluorescence visualization imaging for tumor diagnosis and treatment. Chinese Chemical Letters, 2024, 35(4): 108689-. doi: 10.1016/j.cclet.2023.108689
15. [15]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
16. [16]
  Zheng Zhao , Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270
17. [17]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
18. [18]
  Ya-Wen Zhang , Ming-Ming Gan , Li-Ying Sun , Ying-Feng Han . Supramolecular dinuclear silver(I) and gold(I) tetracarbene metallacycles and fluorescence sensing of penicillamine. Chinese Journal of Structural Chemistry, 2024, 43(9): 100356-100356. doi: 10.1016/j.cjsc.2024.100356
19. [19]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
20. [20]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(163)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142