Monophosphoryl lipid A analogues with varying 3-O-substitution: synthesis and potent adjuvant activity

Jiang, Zi‐Hua; Budzyński, W; Qiu, Dongxu; Damayanthi, Y.; Koganty, R. Rao

doi:10.1016/j.carres.2007.01.012

Cited by 39 publications

(30 citation statements)

References 33 publications

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“…Three such analogues, synthesized by different substitutions at 3-O-position of the reducing sugar, were all found as effective as the natural compound in inducing antigen specific T-cell proliferation and interferon- production with a liposome vaccine [319]. A hexaacylated lipid A derivative was recently found to be more potent than MPL on DC maturation and expression of cytokines/chemokines [305].…”

Section: Monophosphoryl Lpid A/lipidsmentioning

confidence: 99%

Selection of Adjuvants for Enhanced Vaccine Potency

Wang¹,

Singh²

2011

WJV

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Section: Monophosphoryl Lpid A/lipidsmentioning

confidence: 99%

Selection of Adjuvants for Enhanced Vaccine Potency

Wang¹,

Singh²

2011

WJV

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“…Some of these molecules exhibit reduced toxicity in respect to wild-type Lipid A (wtLipid A) and promoted protective immune responses after vaccination [86]. Consequently, these compounds were proposed as alternative enhancers of immune response to the current approved adjuvants [103][104][105][106] (Table 1). An advantage of these molecules over MPL ® is that the synthesis can be done resulting in higher purity and lower costs.…”

Section: Synthesis Of Lipid a Analogousmentioning

confidence: 98%

The Role of Bacterial Lipopolysaccharides as Immune Modulator in Vaccine and Drug Development

Arenas

2012

EMIDDT

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Bacterial lipopolysaccharide (LPS, endotoxin) is the major constituent of the outer membrane of Gram-negative bacteria. LPS can cause a variety of immune- and cellular disorders that lead to lethal effects and clinical manifestations of infectious diseases. Several molecular and cellular in vitro techniques, besides synthesis of analogous molecules of the LPS active region, have provided insight in the molecular mechanisms of LPS bioactivity in cellular systems. These advances have facilitated the application of diverse LPS-based molecules in relevant areas such as vaccine technology, allergen immunotherapy, treatment of immune-related diseases/disorders, LPS-related inflammatory processes and sepsis. The purpose of this review is to examine the progress in the generation of new LPS-based molecules and their therapeutic potential.

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“…However, MPLAs derived from bacterial sources are heterogeneous and thus lack consistency in structure, property, and biological performance. To overcome this problem and to find new MPLA adjuvants with improved immunostimulatory properties, various MPLA derivatives with defined structures have been designed, synthesized, and immunologically evaluated …”

Section: Chemical Synthesis Of Lipid a And Its Derivativesmentioning

confidence: 99%

Progress in the synthesis and biological evaluation of lipid A and its derivatives

Gao

Guo

2017

Medicinal Research Reviews

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Lipid A is one of the core structures of bacterial lipopolysaccharides (LPSs), and it is mainly responsible for the strong immunostimulatory activities of LPS through interactions with the Toll-like receptors and other molecules in the human immune system. To obtain structurally homogeneous and well-defined lipid As and its derivatives in quantities meaningful for various biological studies and applications, their chemical synthesis has become a focal point. This review has provided a survey of significant progresses made in the synthesis of lipid A, and its derivatives that carry diverse saturated and unsaturated lipids, have the phosphate group at its reducing end replaced with a more stable phosphate or carboxyl group, or lack the reducing end phosphate or both phosphate groups, as well as progresses in the synthesis of LPS analogs and other lipid A conjugates. These synthetic molecules have facilitated the elucidation of the structure-activity relationships of lipid A useful for the design and development of lipid A based therapeutics, such as those utilized to treat sepsis, and other medical applications, for example the use of monophosphoryl lipid A as a carrier molecule for the study of fully synthetic self-adjuvanting conjugate vaccines. These topics are also briefly covered in the current review.

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Monophosphoryl lipid A analogues with varying 3-O-substitution: synthesis and potent adjuvant activity

Cited by 39 publications

References 33 publications

Selection of Adjuvants for Enhanced Vaccine Potency

Selection of Adjuvants for Enhanced Vaccine Potency

The Role of Bacterial Lipopolysaccharides as Immune Modulator in Vaccine and Drug Development

Progress in the synthesis and biological evaluation of lipid A and its derivatives

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