Specific Interaction between an Oligosaccharide on the Tumor Cell Surface and the Novel Antitumor Agents, Sulfoquinovosylacylglycerols

Ohta, Keisuke; Mizushina, Yoshiyuki; Yamazaki, Takayuki; Hanashima, Shinya; Sugawara, Fumio; Sakaguchi, Kengo

doi:10.1006/bbrc.2001.5852

Cited by 21 publications

(5 citation statements)

References 13 publications

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“…Recently, in our ongoing research on immunomodulatory substances, we reported the pharmacological development of the non-natural 1,2- O -distearoyl-3- O -β- d -sulfoquinovosylglycerol, here named Sulfavant A ( 1 ) ( Figure 1 ), as a prototype for a new class of molecular adjuvants based on a sulfolipid skeleton [ 4 ]. This family of products is structurally inspired by the natural α- d -sulfoquinovosyl-diacylglycerols (α-SQDG), bioactive metabolites bearing a 6-sulfonic function on d -glucose (sulfoquinovose) linked to a glycerol moiety with two fatty acyl chains [ 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. The natural sulfoglycoglycerolipids are marked by the α-configuration of the anomeric carbon and the β-configuration type is not present in nature.…”

Section: Introductionmentioning

confidence: 99%

Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants

et al. 2017

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Vaccines play a primary role in the protection of human health by preventing infectious and chronic diseases. Recently we have reported 1,2-O-distearoyl-3-O-β-d-sulfoquinovosylglycerol (β-SQDG18), here named Sulfavant A (1), which shows promising properties as a new molecular adjuvant in in vitro and in vivo tests. In the present manuscript, we provide full details about a synthetic strategy for the preparation of 1, including a discussion of chemical determinants of the activity and the major technical hurdles we faced during the study. Synthesis of Sulfavant A (1) is achieved by a versatile procedure based on a trichloroacetimidate methodology and peracetate sugar precursors. The final design opens possibilities for the preparation of a series of interesting analogs for further pharmacological optimization and development, including derivatives containing different saturated and polyunsaturated fatty acids (e.g., 17 and 22).

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Section: Introductionmentioning

confidence: 99%

Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants

et al. 2017

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“…Sulfoquinovosyl acylglycerol (SQAG) 25 was isolated from sea algae and characterized by Sakaguchi et al, and 25 and its derivative sulfoquinovosyl acylpropanediol (SQAP) 26 were reported to be accumulated in cancer cells and exhibit weak toxicity against normal cells (Figure 13a) [33]. Because the modification of the long alkyl chain of SQAG has negligible effect on its biological activity, the design and synthesis of SQAP derivatives 27 and 28 containing a boron cluster unit and iodine atoms as BNCT agents and imaging agents for X-ray computed tomography (CT) were conducted [34,35].…”

Section: Design and Synthesis Of Boron-containing Sugars For Bnctmentioning

confidence: 99%

Design, Synthesis, and Biological Applications of Boron-Containing Polyamine and Sugar Derivatives

Aoki¹,

Ueda²,

Tanaka³

et al. 2022

Characteristics and Applications of Boron

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Boron (B), an element that is present in ultratrace amounts in animal cells and tissues, is expected to be useful in many scientific fields. We have found the hydrolysis of C–B bond in phenylboronic acid-pendant cyclen (cyclen = 1,4,7,10-tetraazacyclododecane) and the full decomposition of ortho-carborane attached with cyclen and ethylenediamines in aqueous solution at neutral pH upon complexation with intracellular metals. The change in the chemical shift of the 11B signals in 11B-NMR spectra of these boron-containing metal chelators can be applied to the magnetic resonance imaging (MRI) of metal ions in solutions and in living cells.

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“…It has recently been reported that some SQDGs show anti-tumor and anti-viral activity (human immunodeficiency virus (HIV) and herpes simplex virus (HSV)) via the inhibition of DNA polymerase. [2][3][4][5][6] Sulfoquinovosyl acylglycerol (SQAG) 1 is one such naturally occurring SQDG derivative that was isolated from sea algae and characterized by Sakaguchi, Sugawara and colleagues 7) (Chart 1). It has been reported that SQAG and its analogue sulfoquinovosyl acylpropandiol (SQAP) 2 accumulates in tumor cells and has a low cytotoxicity against normal cells.…”

mentioning

confidence: 99%

Concise and Versatile Synthesis of Sulfoquinovosyl Acyl Glycerol Derivatives for Biological Applications

Tanaka

Sawamoto

Aoki

2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sulfoquinovosyl acylpropanediol (SQAP), a chemically modified analogue of sulfoquinovosyl acylglycerol (SQAG) that occurs in sea algae, has been reported to show a variety of biological activities, including accumulation in tumor cells and the inhibition of tumor cell growth. We report herein on a new concise and versatile synthesis of SQAP itself and derivatives bearing iodoaryl groups and boronclusters. This method should be useful for the design and synthesis of SQAG/SQAP derivatives for diagnosis and the treatment of cancer and related diseases.

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Specific Interaction between an Oligosaccharide on the Tumor Cell Surface and the Novel Antitumor Agents, Sulfoquinovosylacylglycerols

Cited by 21 publications

References 13 publications

Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants

Chemical Synthesis of Marine-Derived Sulfoglycolipids, a New Class of Molecular Adjuvants

Design, Synthesis, and Biological Applications of Boron-Containing Polyamine and Sugar Derivatives

Concise and Versatile Synthesis of Sulfoquinovosyl Acyl Glycerol Derivatives for Biological Applications

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