How does aggregation of doxorubicin molecules affect its solvation and membrane penetration?
文献情報
Sadaf Shirazi-Fard, Amin Reza Zolghadr
Intermolecular interactions of drug molecules can lead to aggregation, which has a significant impact on their application. This problem might escape the attention when studying their solubility as small aggregates might behave almost as single molecules. We studied the aggregation behaviour of doxorubicin (DOX) molecules through density functional (DFT) methods and molecular dynamics (MD) simulations in water, dimethylformamide (DMF), ethanol (EtOH), and dimethyl sulfoxide (DMSO). We described the degree of aggregation by MD-calculated radial distribution function, combined radial/angular distribution functions, autocorrelation functions, and the number of hydrogen bonds of individual DOX and solvent atoms. MD-calculated diffusion coefficients for DOX decrease along the series water > DMF > EtOH > DMSO (0.101 × 10−9, 0.047 × 10−9, 0.025 × 10−9, and 0.007 × 10−9 m2 s−1, respectively) consistent with increasing aggregation found in the MD simulations. These aggregates have different characters, depending on the DOX⋯solvent interactions, and include hydrogen bonding and π-stacking. Even though the solvation energy of a single DOX molecule in DMSO (−24.8 kcal mol−1) is higher than in other solvents, the formation of larger aggregates in this solvent prevents proper solvation. Further, the orientation of doxorubicin molecules at octanol/water and dipalmitoylphosphatidylcholine (DPPC)/water interfaces was studied with two different orientations from the bivariate maps. In the case of the DPPC/water interface, the anthracycline part points toward the aqueous phase, while this part is oriented almost parallel to the octanol/water interface in DMSO.
関連文献
Investigating the effect of Ag nanocube polydispersity on gap-mode SERS enhancement factors
Tyler J. Dill, Matthew J. Rozin, Eric R. Brown, Stephen Palani, Andrea R. Tao
DOI: 10.1039/C6AN00212A
Correction: Shell-isolated nanoparticle-enhanced Raman spectroscopy study of the adsorption behaviour of DNA bases on Au(111) electrode surfaces
Bao-Ying Wen, Xi Jin, Yue Li, Ya-Hao Wang, Chao-Yu Li, Miao-Miao Liang, Rajapandiyan Panneerselvam, Qing-Chi Xu, De-Yin Wu, Zhi-Lin Yang, Jian-Feng Li, Zhong-Qun Tian
DOI: 10.1039/C6AN90033J
A rhodol-hemicyanine based ratiometric fluorescent probe for real-time monitoring of glutathione dynamics in living cells
Minghao Ren, Linfang Wang, Xin Lv, Yuanqiang Sun, Hu Chen, Keyuan Zhang, Qi Wu, Yurong Bai, Wei Guo
DOI: 10.1039/C9AN01852B
A new label-free fluorescent sensor for human immunodeficiency virus detection based on exonuclease III-assisted quadratic recycling amplification and DNA-scaffolded silver nanoclusters
Wen Yang, Jianniao Tian, Lijun Wang, Shui Fu, Hongyun Huang, Yanchun Zhao, Shulin Zhao
DOI: 10.1039/C6AN00184J
SERS monitoring the dynamics of local pH in lysosome of living cells during photothermal therapy
Rongxing Luo, Yinhui Li, Qifeng Zhou, Jing Zheng, Dandan Ma, Pinting Tang, Sheng Yang, Zhihe Qing
DOI: 10.1039/C6AN00467A
Feature engineering applied to intraoperative in vivo Raman spectroscopy sheds light on molecular processes in brain cancer: a retrospective study of 65 patients
Rajeev Yadav, Rajeev Agarwal, Samuel Kadoury, Dominique Trudel, Marie-Christine Guiot, Kevin Petrecca
DOI: 10.1039/C9AN01144G
Rapid and improved characterization of therapeutic antibodies and antibody related products using IdeS digestion and subunit analysis
Jonathan Sjögren, Fredrik Olsson, Alain Beck
DOI: 10.1039/C6AN00071A
Mass spectrometric analysis of PTM dynamics using stable isotope labeled metabolic precursors in cell culture
Alienke van Pijkeren, Rainer Bischoff
DOI: 10.1039/C9AN01258C
The origin of the band at around 730 cm−1 in the SERS spectra of bacteria: a stable isotope approach
Patrick Kubryk, Reinhard Niessner, Natalia P. Ivleva
DOI: 10.1039/C6AN00306K
こちらもおすすめ
2-ブロモ-9,9-ジフェニル-9H-フルオレンの主な用途は何ですか?
2-溴-9,9-二苯基芴は、医薬品、工業材料、有機合成の研究分野で応用されます。特に、レーザー材料や機能性ポリマーの合成に使用されることがあります。また、蛍光色...
四氯化铱の市場動向や研究トレンドはどうですか?
四氯化铱の市場は研究開発分野で注目されており、特にナノ技術や金属有機框架(MOFs)の分野での需要が増加傾向にあります。価格は安定しており、中国や韓国での生産が...
1-(4-溴-3-氟苯基)-2-氯乙酮を含む廃棄物はどのように処理すべきですか?
1-(4-溴-3-氟苯基)-2-氯乙酮 (CAS番号: 1260857-14-4) の廃棄物は専門的な廃棄処理が必要です。まず、廃棄物は密閉された容器に収集し、...
苦参酚Kとは何ですか?
苦参酚Kは、CAS番号101236-49-1を持つ化合物で、主に天然由来の生薬から抽出されます。この化合物は、抗炎症作用や抗癌作用を持つことが報告されています。
POTASSIUM (1-(TERTBUTOXYCARBONYL)AZETIDIN-3-YL)TRIFLUOROBORATE を含む廃棄物はどのように処理すべきですか?
POTASSIUM (1-(TERTBUTOXYCARBONYL)AZETIDIN-3-YL)TRIFLUOROBORATE を含む廃棄物は、まず安全なエント...
4-庚基-4’-联苯羧酸の市場動向や研究トレンドはどうですか?
4-庚基-4’-聯苯羧酸は、特殊化学品や合成化学の分野で用いられる化学物質ですが、市場動向としては、研究開発の進展とともに需要が増加しています。また、環境配慮型...
6-ブロモ-3-メトキシ-1-フェニル-1H-インドゾールを含む廃棄物はどのように処理すべきですか?
6-ブロモ-3-メトキシ-1-フェニル-1H-インドゾールを含む廃棄物は、適切な化学廃棄処理が必要です。通常、廃棄物は密閉容器に収集され、専門の廃棄処理業者に引...
4,4-二甲基-2-吡咯烷酮はどの業界で使用されていますか?
4,4-二甲基-2-吡咯烷酮は医薬、ポリマー、センサー、半導体などの業界で広く使用されています。特に溶媒としての性能が高く評価されています。
掲載誌
New Journal of Chemistry

NJC (New Journal of Chemistry) is a broad-based primary journal encompassing all branches of chemistry and its sub-disciplines. It contains full research articles, communications, perspectives and focus articles. This well-established journal, owned by the Centre National de la Recherche Scientifique (CNRS) of France, has been co-published with the Royal Society of Chemistry since January 1998. NJC is the forum for the publication of high-quality, original and significant work that opens new directions in chemistry or other scientific disciplines. In addition to having a significant chemical component, work published in NJC must demonstrate that it will have an impact on areas of research other than that of the reported work.












![5-Acetyl-2,3-dihydrobenzo[b]furan structure 5-Acetyl-2,3-dihydrobenzo[b]furan structure](https://static.chemtradehub.com/structs/908/90843-31-5-eea4.webp)

