Optimization of hypocrellin B derivative amphiphilicity and biological activity

Liu, Xin; Xie, Jie; Zhang, Luyong; Chen, Hongxia; Gu, Ying; Zhao, Jingquan

doi:10.1007/s11434-009-0036-3

Cited by 4 publications

(3 citation statements)

References 28 publications

(32 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[25,[30][31][32][33][34][35][36] Different chemical modifications on HB induce variations in absorption properties and 1 O 2 yields. [37][38][39][40][41][42] Amino-substituted HB derivatives at position 2 could remarkably enhance longerwavelength absorption bands near 600 nm compared with that of HB (Scheme 1). Substitution on the carbonyl groups (position 3 or 4, Scheme 1) of HB could distinctly red-shifted the absorption wavelength longer than 600 nm.…”

Section: Introductionmentioning

confidence: 99%

“…In previous studies, functional groups, such as halogen, aliphatic amine, and amino acids, were introduced to a specific site in HB [25,30–36] . Different chemical modifications on HB induce variations in absorption properties and 1 O 2 yields [37–42] . Amino‐substituted HB derivatives at position 2 could remarkably enhance longer‐wavelength absorption bands near 600 nm compared with that of HB (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Near‐Infrared Hypocrellin Derivatives for Synergistic Photodynamic and Photothermal Therapy

Ding

Liu

et al. 2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

Hypocrellin B (HB) derived from naturally produced hypocrellins has attracted considerable attention in photodynamic therapy (PDT) because of its excellent photosensitive properties. However, the weak absorption within a "phototherapy window" (600-900 nm) and poor water solubility of HB have limited its clinical application. In this study, two HB derivatives (i. e., HE and HF) were designed and synthesized for the first time by introducing two different substituent groups into the HB structure. The obtained derivatives showed a broad absorption band covering the near-infrared (NIR) region, NIR emission (peaked at 805 nm), and singlet oxygen quantum yields of 0.27/0.31. HE-PEG-NPs were also prepared using 2-distearoyl-sn-glycero-3-phosphoethanolamine-N-[methoxy(polyethyleneglycol)-2000] (DSPE-mPEG2000) to achieve excellent dispersion in water and further explored their practical applications. HE-PEG-NPs not only retained their 1 O 2-generating ability, but also exhibited a photothermal conversion efficiency of 25.9%. In vitro and in vivo therapeutic results revealed that the synergetic effect of HE-PEG-NPs on PDT and photothermal therapy (PTT) could achieve a good performance. Therefore, HE-PEG-NPs could be regarded as a promising phototheranostic agent.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Near‐Infrared Hypocrellin Derivatives for Synergistic Photodynamic and Photothermal Therapy

Ding

Liu

et al. 2020

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

“…Besides what has been mentioned, another advantage of hypocrellins is that the chemical structures are readily modifiable by introducing various substituent(s) to site 2, 5, 8, 11, 13, 14, or 17, but singlet oxygen yields of the derivatives vary greatly. Generally, 2-, 5-, or 8-substituted derivatives exhibit a low singlet oxygen ( 1 O 2 ) yield − and 13-, 14-, or 17-substituted derivatives a higher 1 O 2 yield. ,, Especially the singlet oxygen yield for 17-(3-amino-1-propanesulfonic acid)-substituted hypocrellin B Schiff base ( 4 ) is almost comparable to that of the parent 2 ; however, it was synthesized in strong alkali solution in a yield of no more than 10%.…”

Section: Introductionmentioning

confidence: 99%

Quantitative and Site-Directed Chemical Modification of Hypocrellins toward Direct Drug Delivery and Effective Photodynamic Activity

et al. 2012

Self Cite

View full text Add to dashboard Cite

For photodynamic therapy (PDT) treatment of microvascular diseases, drugs are delivered via blood circulation and the targets are vasculature endothelial cells, for which the contradictory requirements of hydrophilicity and lipophilicity of the drugs have been achieved by liposome preparations. Herein, it is demonstrated that the drug delivery and target affinity are achieved by a single chemical compound, hypocrellin B (HB) derivative 6 selected from three novel aminoalkanesulfonic acid HB derivatives, 5-7. 6 exhibits a much higher PDT activity (IC(50) = 22 nM) on human gastric carcinoma BGC823 cells than HB, while it has no cellular toxicity in the dark. On the basis of estimation of the clinically required concentration according to relative PDT activity and clinical criteria, it can be predicted that 6 is directly deliverable to and PDT effective on target cells. The enhanced red absorption and superhigh photoactivity suggest that 6 is more powerful for PDT of tumors than HB.

show abstract

Light activated drug deliveryplatform for dental applications- current technologies and future perspectives

Krishnaswami,

Sugumaran,

Jacob Raja

et al. 2024

Laser Dent Sci

View full text Add to dashboard Cite

Optimization of hypocrellin B derivative amphiphilicity and biological activity

Cited by 4 publications

References 28 publications

Near‐Infrared Hypocrellin Derivatives for Synergistic Photodynamic and Photothermal Therapy

Near‐Infrared Hypocrellin Derivatives for Synergistic Photodynamic and Photothermal Therapy

Quantitative and Site-Directed Chemical Modification of Hypocrellins toward Direct Drug Delivery and Effective Photodynamic Activity

Light activated drug deliveryplatform for dental applications- current technologies and future perspectives

Contact Info

Product

Resources

About