D-10-camphorsulfonic acid: Safety evaluation

Fehr, Markus; Appl, Ádám; Esdaile, David J.; Naumann, Steffen C.; Schulz, Markus; Dahms, Irina

doi:10.1016/j.mrgentox.2020.503257

Cited by 6 publications

(6 citation statements)

References 9 publications

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“…All the detectable molecules we found are shown in Fig. 5a; interestingly, most of them have either directly biological functions 84,85 or are important pharmaceutical intermediates. [86][87][88][89] Computational results show that these molecules have a comparable size to that of 2 (Table S14 †), suggesting they are included in the cages of 1 : 1 stoichiometry.…”

Section: Ccd and 1 H Nmr Chemical Shifts Utilized For Guest Fingerpri...mentioning

confidence: 89%

Guest differentiation and fingerprinting based on the conformational diversity of a dynamic corannulene-based cage

et al. 2023

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Section: Ccd and 1 H Nmr Chemical Shifts Utilized For Guest Fingerpri...mentioning

confidence: 89%

Guest differentiation and fingerprinting based on the conformational diversity of a dynamic corannulene-based cage

et al. 2023

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“…SLS is used in pharmaceutical formulations for solubilization and permeation enhancement, and its potential to form lipid soluble IL with ionizable drugs has been previously demonstrated. , (+)-10-Camphorsulfonic acid (camsylate) is a cyclic sulfonate anion with good oral safety, and camsylate salts of weakly basic hydrophobic drugs such rucaparib and amlodipine are approved for oral use. , Taurocholic acid is an endogenous sulfonate containing bile acid that has been used as an absorption enhancer by increasing the solubility of the hydrophobic drug and promoting its chemical and enzymatic stability. − However, to date, the potential of camsylate and taurocholate to transform drug into IL has not been explored. The theoretical basic p K a of BX795 predicted by MarvinSketch (Version: 21.2) is 3.68, whereas the p K a values of docusate, taurocholate, lauryl sulfate, and (+)-10-camphorsulfonic acid are −0.75, 1.4, −1.5, and 1.2 respectively.…”

Section: Discussionmentioning

confidence: 99%

Oral Self-Nanoemulsifying System Containing Ionic Liquid of BX795 Is Effective against Genital HSV-2 Infection in Mice

Sutar,

Singh,

Dhoble

et al. 2023

ACS Infect. Dis.

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BX795 is an emerging drug candidate that has shown a lot of promise as a next-generation non-nucleoside antiviral agent for the topical treatment of herpes simplex virus type-1 (HSV-1) and herpes simplex virus type-2 (HSV-2) infections. Our studies indicated that BX795 has limited oral bioavailability, which could be attributed to its low and pH-dependent solubility. Lipidbased formulations such as self-nanoemulsifying systems (SNESs) can improve the solubility and oral bioavailability of BX795, but the poor lipid solubility of BX795 further limits the development of SNES. To improve the loading of BX795 into SNES, we evaluated the ability of various bulky and biocompatible anions to transform BX795 into an ionic liquid (IL) with higher lipid solubility. Our studies showed that sodium lauryl sulfate and docusate sodium were able to transform BX795 into IL. Compared to pure BX795, the developed BX795 ILs showed differential in vitro cytocompatibility to HeLa cells but exhibited similar in vitro antiviral activity against HSV-2. Interestingly, BX795 docusate (BX795-Doc), an IL of BX795 with ∼135-fold higher lipid solubility than pure BX795, could be successfully incorporated into an SNES, and the developed BX795-Doc-SNES could readily form nanoemulsions of size ≤200 nm irrespective of the pH of the buffer used for dilution. Our in vitro studies showed that BX795-Doc-SNES retained the inherent antiviral activity against HSV-2 and showed similar in vitro cytocompatibility, indicating the availability of BX795 from the SNES in vitro. Finally, orally delivered SNES containing BX795-Doc showed a significant reduction in HSV-2 infection in mice compared to the untreated control. Thus, the transformation of BX795 into IL and the subsequent incorporation of the BX795 IL into the SNES are an effective strategy to improve oral therapy of genital herpes infection.

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“…Therefore, we searched for an alternative TBS deprotection reagent that is easily removed. Camphorsulfonic acid [(-)-CSA] [42,43] emerged as a reagent of choice; it is an acid derived from camphor that has low sensitivity to air, is compatible with water, and is environmentally friendly. Treatment of 7 with (-)-CSA in MeOH leads to the 2 ,3 -didehydro-2 ,3 -dideoxynucleosides of uracil and thymine 8a and 8b with 92% and 95% yield, respectively.…”

Section: Scheme 1 Regioselective Enzymatic Acylation Ofmentioning

confidence: 99%

Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives

Martín-Nieves

Sanghvi²,

Fernández

et al. 2022

Molecules

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An improved protocol for the transformation of ribonucleosides into 2’,3’-dideoxynucleoside and 2’,3’-didehydro-2’,3’-dideoxynucleoside derivatives, including the anti-HIV drugs stavudine (d4T), zalcitabine (ddC) and didanosine (ddI), was established. The process involves radical deoxygenation of xanthate using environmentally friendly and low-cost reagents. Bromoethane or 3-bromopropanenitrile was the alkylating agent of choice to prepare the ribonucleoside 2′,3′-bisxanthates. In the subsequent radical deoxygenation reaction, tris(trimethylsilyl)silane and 1,1’-azobis(cyclohexanecarbonitrile) were used to replace hazardous Bu3SnH and AIBN, respectively. In addition, TBAF was substituted for camphorsulfonic acid in the deprotection step of the 5′-O-silyl ether group, and an enzyme (adenosine deaminase) was used to transform 2’,3’-dideoxyadenosine into 2’,3’-dideoxyinosine (ddI) in excellent yield.

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D-10-camphorsulfonic acid: Safety evaluation

Cited by 6 publications

References 9 publications

Guest differentiation and fingerprinting based on the conformational diversity of a dynamic corannulene-based cage

Guest differentiation and fingerprinting based on the conformational diversity of a dynamic corannulene-based cage

Oral Self-Nanoemulsifying System Containing Ionic Liquid of BX795 Is Effective against Genital HSV-2 Infection in Mice

Sustainable Protocol for the Synthesis of 2′,3′-Dideoxynucleoside and 2′,3′-Didehydro-2′,3′-dideoxynucleoside Derivatives

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