Novel phytol derived immunoadjuvants and their use in vaccine formulations

a vaccine formulation and immunoadjuvant technology, applied in the field of immunoadjuvants, can solve the problems of inducing severe side reactions, severe adverse inflammatory reactions, and toxic adjuvants, and achieve the effect of enhancing the immunogenicity of a vaccine composition and inducing the immunogenic respons

Inactive Publication Date: 2005-07-21
GHOSH SWAPAN K
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008] In another form, the present invention provides a method of enhancing the immunogenicity of a vaccine composition. The method comprises selecting an antigen that induces a desired immunogenic response in a mammal; combining the antigen with phytol, isophytol, or a phytol derivative in a physiologically acceptable carrier; and treating a mammal with the vaccine composition in an amount effective to induce the immunogenic response. In preferred embodiments, the vaccine formulation includes the antigen in a lower effective dose than another vaccine formulation that includes the same antigen but without the benefit of or in the absence of the phytol or a phytol derivative. The preferred vaccine formulation still elicits the desired immunogenic response substantially the same as the vaccine that does not include the phytol, isophytol, or phytol derivative.

Problems solved by technology

However, many adjuvants, while effective, are also often toxic to humans.
These adjuvants can cause severe adverse inflammatory reactions.
Therefore, while adjuvants can be effective in enhancing the immunogenicity of the antigens in the vaccines, they can also induce severe side reactions.
While this adjuvant presents fewer instances of adverse reactions, it is not as effective in inducing humoral or cellular immune responses as other adjuvants, such as incomplete Freund's adjuvant (IFA) or complete Freund's adjuvant (CFA, which is IFA plus mycobacterial components).

Method used

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  • Novel phytol derived immunoadjuvants and their use in vaccine formulations
  • Novel phytol derived immunoadjuvants and their use in vaccine formulations
  • Novel phytol derived immunoadjuvants and their use in vaccine formulations

Examples

Experimental program
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Effect test

example 1

Preparation of 2,3-Dihydrophytol (phytanol or H-phytol)

[0043]

[0044] To a solution of 1.00 g phytol in dry tetrahydrofuran was added 0.10 g 5% palladium on carbon. The mixture was allowed to stir 24 h under hydrogen at 1 atm. The catalyst was removed by centrifugation and the solvent was then removed by rotary evaporation. The resulting oil was purified by molecular distillation at about 100° C. and 0.1 mm Hg to give a colorless oil: 1H NMRδ (ppm) 0.90 (d, ˜15H), 1-1.8 (m, ˜25H), 3.7 (t, 2H).

[0045] Hydrogenation of phytol can also be accomplished using Raney nickel and hydrogen to yield phytanol as referenced in Bendavid, A., Burns, C. J., Leslie, D. F., Hashimoto, K., Ridley, D. D., Sandanayake, S., and Wieczorek L., J. Org. Chem. (2001), 66, 3709-3716; Kim, T., Chan, K. C, and Crooks, R. M., J. Am. Chem. Soc. (1997) 119, 189; and Jellum, E., Eldjarn, L., and Try, K., Acta Chem. Scand. (1966), 20, 2335.

example 2

Preparation of Halogenated Phytol / Phytanol

[0046] Hologenated phytol can be prepared according the procedure outlined below. The procedure shown below is a general one and can be found in the above references, and in particular in Bendavid, A., Burns, C. J., Leslie, D. F., Hashimoto, K., Ridley, D. D., Sandanayake, S., and Wieczorek, L., J. Org. Chem. (2001), 66, 3709-3716.

example 3

Preparation of Phytanyl Glucose / Phytanyl Mannose

[0047] Phytanyl glucose has been previously reported (1, 2). The procedure used by Hato and coworkers (2) to make this compound in moderate yield is the same procedure that they used to make some similar acetals several years earlier (3). However, recent reports (4, 5, 6) of the preparation of some similar lipidated carbohydrate acetals appear to offer even better ways of making phytanyl glucose. Hinguchi and coworkers (4) converted glucose acetate to a bromide by treating with HBr and then converted this to an acetal by treating it with a long-chain alcohol, AgClO4 and AgCO3. It is envisioned that a procedure, as shown below, can be used with phytanol.

[0048] Alternatively, a phytanyl glucose conjugate can be prepared by adapting a procedure reported by Clausen and coworkers (glucose acetate, ROH, BF3—OEt2, CH2Cl2) (5) or by the procedure disclosed by Konstantinovic and coworkers (glucose acetate, ROH, SnCl4) (6). A similar scheme c...

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Abstract

This invention relates to a novel immunoadjuvant, an adjuvant component, and vaccines containing the adjuvant component. The adjuvant includes phytol or a phytol derivative. The adjuvant component, when combined with a soluble or particulate antigen, provides a vaccine with an enhanced ability to induce both humoral and cytotoxic immune responses while displaying reduced toxicity and / or adverse side effects over vaccines that include the antigen but without the benefit of this adjuvant component.

Description

BACKGROUND [0001] The present invention relates to immunoadjuvants that include phytol or a phytol derivative and the use of the immunoadjuvants in a pharmaceutical formulation to effect treatment by augmenting immunogenicity and effectiveness of vaccines. [0002] Vaccines are used to provide effective immunity to prevent infection and even cancer. With the introduction of widespread immunization in the last century, diseases such as diphtheria, tetanus, polio, small pox, and pertussis have been significantly reduced if not eliminated. Moreover, new generations of vaccines are constantly being sought after for treatment of diseases such as AIDS, hepatitis, and herpes. [0003] Vaccines are meant to stimulate the individual's specific and non-specific immune responses. Vaccines are accompanied by an adjuvant which can increase the efficacy of the vaccine by a variety of actions, including retaining the vaccine in the body or at the site of injection for a significantly long period of ti...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/045A61K39/39
CPCA61K31/045A61K2039/55511A61K39/39
Inventor GHOSH, SWAPAN K.
Owner GHOSH SWAPAN K
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