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Hydrophobin mimics: process for preparation thereof

a technology of hydrophobin and mimics, applied in the field of hydrophobin mimics, can solve the problems of limiting protein nanotechnology application, difficult to predict the effects of various mutations, and high-throughput screening which may not be feasible for all proteins

Active Publication Date: 2017-08-17
INDIAN INST OF SCI EDUCATION & RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides hydrophobin mimics of varying size and shapes for use in bio-nano technology. These mimics can self-assemble or in a specified chemical environment to yield supramolecular protein assemblies. The mimics can be prepared by coupling a protein with an amphiphilic activity probe (AAP) using click chemistry. The AAPs can be reacted with a hydrophobic azide to obtain the mimics. The mimics can be used in various applications such as drug development and material science. The invention also provides a process for preparing the AAPs and a method for purifying the mimics.

Problems solved by technology

However, the technique has the major drawback in that in most instances the detailed structural knowledge of protein is often unavailable and further it may sometimes become difficult to predict the effects of various mutations.
The drawback of the method is that it requires high-throughput screening which may not be feasible for all proteins.
Further, the functional group diversity in natural protein is limited to standard 20 amino acids and therefore diversity of protein scaffold is small which limits protein nanotechnology application.
Moreover, most of the work related to protein nanotechnology is carried out using standard genetic engineering which is costly.
Yet another objective is to create a library of hydrophobin mimics by tuning the protein head group, linker and hydrophobic part synthetically which is difficult to achieve in other reported method to cater to the needs of bio-nanotechnology.

Method used

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  • Hydrophobin mimics: process for preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

of 1-Tail (1T) Hydrophobic Azides

[0110]1.1 Synthesis of 4-hydroxybenzyl Alcohol

[0111]To a suspension of 4-hydroxybenzaldehyde in DCM, silica was added, followed by sodium borohydride. The reaction mixture was stirred for five minutes prior to the dropwise addition of methanol after which it was left to stir for a further thirty minutes. The entire reaction mixture was poured onto a short silica pad and was flushed with acetone. Combined organic layer was dried over Na2SO4 and evaporated under vacuum to get product which was used without further purification.

[0112]1.2 Synthesis of 1-Tail Alkyl Alcohol

[0113]4-hydroxybenzyl alcohol (1.0 eq), alkyl bromide (1.1 eq), K2CO3 (1.2 eq), crown ether (0.1 eq) were taken in an oven dried RBF. The flask was then purged with nitrogen and acetone was added under stirring to dissolve the mixture and refluxed for 24 hours. Upon completion, reaction mixture was concentrated and extracted thrice with DCM. Combined organic layer was dried over Na2SO4 a...

example 2

rocedures for Synthesis of 2-Tail (2T) Hydrophobic Azides

[0118]2.1 Synthesis of Ethyl 3, 5-dihydroxybenzoate

[0119]3,5-dihydroxybenzoic acid (35 g, 227 mmol) was taken in an oven dried RBF, ethyl alcohol (250 mL) was added and dissolved with stirring, sulphuric acid (24 mL) was added drop wise and refluxed for 22 hours. Upon completion, reaction mixture was neutralized with aqueous NaHCO3 and extracted thrice with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulphate (Na2SO4) and concentrated under vacuum to get crude product, which was further purified using silica gel column chromatography using ethyl acetate / hexane (30:70) to get white colour solid (41 g, 214 mmol, 94%).

[0120]2.2 Synthesis of 2-Tail Alkyl Esters

[0121]Ethyl 3,5-dihydroxy benzoate (1.0 eq), alkyl bromide (2.5 eq), K2CO3(3.5 eq), KI (0.05 eq) were taken in an oven dried RBF. The flask was then purged with nitrogen; DMF was added under stirring to dissolve the mixture and refluxed...

example 3

rocedure for Synthesis of 3-Tail (3T) Hydrophobic Azides

[0128]3.1 Synthesis of Ethyl 3,4,5-trihydroxybenzoate

[0129]To the stirring solution of 3,4,5-trihydroxybenzoic acid (6 g, 38 mmol) in ethyl alcohol (70 mL), sulphuric acid (4 mL) was added drop wise and refluxed for 22 hours. Reaction mixture was neutralized with aqueous Na2CO3 solution, extracted thrice with ethyl acetate. The combined organic layer was washed with brine and concentrated under vacuum to get crude product which was purified using silica gel column chromatography using ethyl acetate / hexane (30:70) to get white colour solid (6.73 g, 36 mmol, 95%).

[0130]3.2 Synthesis of 3-Tail Esters

[0131]Ethyl 3,4,5-trihydroxybenzoate of step (3.1) (1.0 eq), alkyl bromide (3.5 eq), K2CO3 (3.5 eq) and KI (0.05 eq) were taken in an oven dried flask. The flask was then purged with nitrogen; DMF was added under stirring to dissolve the mixture and refluxed for 12 hours. Upon completion, reaction mixture was neutralized with acidic wa...

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Abstract

The present invention discloses hydrophobin mimics of formula (I) comprising a protein head group, hydrophilic linker and hydrophobic tail and to a process for synthesis of library of hydrophobin mimics thereof. The hydrophobin mimics of the present invention self-assemble to form protein nanoparticles / nanocontainer either alone or in a specified chemical environment. The hydrophobin mimics (I) of the present invention find application in area of bio-nanotechnology.

Description

TECHNICAL FIELD OF THE INVENTION[0001]The present invention relates to Hydrophobin mimics of formula (I) comprising a protein head group, hydrophilic linker and hydrophobic tail and to a process for synthesis of library of hydrophobin mimics thereof. The hydrophobin mimics of the present invention self-assemble to form protein nanoparticles / nanocontainer either alone or in a specified chemical environment. The hydrophobin mimics (I) of the present invention find application in bio-nanotechnology.BACKGROUND AND PRIOR ARTS[0002]Biomolecular nanotechnology is one of the emerging fields to design biological structures on natural scale. The technology includes using DNA, RNA, proteins, peptides, carbohydrates as templates for providing nanomaterials as multivalent scaffolds for drug delivery, enzyme inhibition and for vaccine development, glycan related biological and medical problems.[0003]Self assembling of the biomaterials particularly composed of nucleic acids, peptides using DNA and...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A23L33/17A61K8/66A61Q17/00C12N9/50A61K51/08A61K49/14A61K49/00C07K1/14A61K39/00A61K9/48
CPCA23L33/17A23V2002/00A61K8/66A61Q17/005A61K47/48369A61K9/4825A61K51/08A61K49/14A61K49/0056C07K1/14C12Y304/21001C12Y304/21004C12Y304/21062C12Y304/21064C12N9/50A61K39/00A61K8/55A61Q19/00B82Y5/00A61K2800/10A61K9/48
Inventor BRITTO, SANDANARAJ SELVARAJREDDY, MULLAPUDI MOHANBHANDARI, PAVANKUMAR JANARDHANRAO, KASULADEVU JAGANNADHA
Owner INDIAN INST OF SCI EDUCATION & RES
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